WEBVTT 00:00:00.000 --> 00:00:02.540 You know, we talk about potential a lot in these 00:00:02.540 --> 00:00:07.820 deep dives. Usually it's about a tech startup 00:00:07.820 --> 00:00:10.539 that almost made it, or maybe a movie that got 00:00:10.539 --> 00:00:12.839 stuck in development hell. It's usually this 00:00:12.839 --> 00:00:15.080 abstract thing. Sure, there could have been stories. 00:00:15.240 --> 00:00:17.480 The ones that got away, they're always fascinating. 00:00:17.859 --> 00:00:21.960 Exactly. But in music, potential is, well, it's 00:00:21.960 --> 00:00:24.100 usually a nice way of saying, didn't quite make 00:00:24.100 --> 00:00:26.309 it. You know, oh, they had so much potential, 00:00:26.350 --> 00:00:29.129 which is really just code for they had one good 00:00:29.129 --> 00:00:32.149 song on the radio in 2004 and then poof, they 00:00:32.149 --> 00:00:34.270 vanished into the ether. It's the one hit wonder 00:00:34.270 --> 00:00:36.509 syndrome. Or you see it with a band that puts 00:00:36.509 --> 00:00:38.670 out a classic first album and then just breaks 00:00:38.670 --> 00:00:40.149 up before the second one, that kind of thing. 00:00:40.390 --> 00:00:44.469 But today, today's Deep Dive, it feels really 00:00:44.469 --> 00:00:47.429 different. I was reading through just the massive 00:00:47.429 --> 00:00:49.609 stack of research you sent over. And by the way, 00:00:49.630 --> 00:00:51.689 thank you for the extra material on that ethylene 00:00:51.689 --> 00:00:53.469 book, which we absolutely need to talk about. 00:00:53.530 --> 00:00:55.750 Oh, for sure. That's a crucial piece of the puzzle. 00:00:55.890 --> 00:00:58.490 Reading all of this, I genuinely got angry. Angry. 00:00:58.609 --> 00:01:00.329 That's a strong reaction. Not usually the one 00:01:00.329 --> 00:01:02.670 we aim for. Yeah. No, it was. It was frustration. 00:01:03.409 --> 00:01:06.530 Because we were looking at a story where the 00:01:06.530 --> 00:01:08.890 potential wasn't theoretical. It wasn't a maybe. 00:01:09.209 --> 00:01:12.079 It was literally. It was being signed on a piece 00:01:12.079 --> 00:01:14.519 of paper. It was days away. It was imminent. 00:01:14.760 --> 00:01:16.799 Yes. We aren't talking about a guy who might 00:01:16.799 --> 00:01:18.939 have become a star. We're talking about a guy 00:01:18.939 --> 00:01:21.280 who was standing on the absolute threshold of 00:01:21.280 --> 00:01:24.140 becoming the king of New York, arguably a billionaire 00:01:24.140 --> 00:01:26.459 mogul right alongside Jay -Z, and then the door 00:01:26.459 --> 00:01:30.379 just slammed shut. That is the perfect way to 00:01:30.379 --> 00:01:33.079 frame the tragedy of Lamont Coleman. Better known 00:01:33.079 --> 00:01:36.099 to the entire world as Big L. The punchline king. 00:01:36.680 --> 00:01:40.519 The lyricist, a legend's legend. But see, here 00:01:40.519 --> 00:01:41.920 is the tension I want to start with, because 00:01:41.920 --> 00:01:44.019 I really need you to explain this to me. If I 00:01:44.019 --> 00:01:47.079 look at the stats, just the raw numbers, Big 00:01:47.079 --> 00:01:50.780 L released exactly one studio album while he 00:01:50.780 --> 00:01:53.459 was alive. Just one. One. And it peaked at number 00:01:53.459 --> 00:01:56.700 149 on the Billboard 200. Which, statistically 00:01:56.700 --> 00:01:59.680 speaking, in the major label system of the 1990s, 00:01:59.680 --> 00:02:01.819 is a commercial flop. There's no other way to 00:02:01.819 --> 00:02:04.409 put it. Right. So if I'm an alien landing on 00:02:04.409 --> 00:02:06.150 Earth and I'm just looking at the spreadsheets, 00:02:06.170 --> 00:02:08.569 Big L is a footnote. He's a blip on the radar. 00:02:09.090 --> 00:02:14.590 But if I talk to Nas, if I talk to Jay -Z or 00:02:14.590 --> 00:02:17.330 Eminem, they talk about this guy like he's a 00:02:17.330 --> 00:02:19.889 deity. A force of nature. Miles literally said 00:02:19.889 --> 00:02:22.569 he was scared to death to rap against him. So 00:02:22.569 --> 00:02:25.949 what is the disconnect here? That's my mission 00:02:25.949 --> 00:02:28.330 for this deep dive. I want to understand how 00:02:28.330 --> 00:02:31.590 a guy with a quote unquote failed debut album. 00:02:32.139 --> 00:02:34.740 became a hip hop god. And we are absolutely going 00:02:34.740 --> 00:02:36.400 to bridge that gap because to understand Big 00:02:36.400 --> 00:02:38.240 L, you can't look at the sales figures. That's 00:02:38.240 --> 00:02:40.219 the wrong metric. You have to look at the mechanics, 00:02:40.340 --> 00:02:42.300 the actual science of what he was doing with 00:02:42.300 --> 00:02:44.240 words. The technique. The technique. We're going 00:02:44.240 --> 00:02:46.199 to talk about something later on called compounding. 00:02:46.199 --> 00:02:47.960 It's a rhyme technique that he had mastered before 00:02:47.960 --> 00:02:50.259 almost anyone else was even attempting it. And 00:02:50.259 --> 00:02:52.580 we have to talk about the what if, the giant 00:02:52.580 --> 00:02:55.919 looming what if of the Rockefeller deal. It might 00:02:55.919 --> 00:02:58.240 be the biggest what if in all of hip hop history. 00:02:59.240 --> 00:03:01.960 We have sources today, including that biography, 00:03:02.199 --> 00:03:04.539 Ethylene, you mentioned, and some very recent, 00:03:04.620 --> 00:03:07.800 very controversial updates from 2025 that paint 00:03:07.800 --> 00:03:10.400 the picture of a guy who is about to merge his 00:03:10.400 --> 00:03:12.860 untouchable underground credibility with Jay 00:03:12.860 --> 00:03:15.500 -Z's unstockable commercial machine. And we're 00:03:15.500 --> 00:03:17.460 also going to get into the darkness. Yeah. I 00:03:17.460 --> 00:03:19.120 mean, you can't tell this story without talking 00:03:19.120 --> 00:03:22.699 about 139th Street, the danger zone, and the 00:03:22.699 --> 00:03:25.479 cold case murder that went unsolved for decades. 00:03:25.560 --> 00:03:28.060 And the prevailing theory that it wasn't just 00:03:28.060 --> 00:03:30.719 random street. violence, that it was a specific 00:03:30.719 --> 00:03:34.400 targeted hit involving a complex, almost Shakespearean 00:03:34.400 --> 00:03:37.639 web of family loyalty and ultimately betrayal. 00:03:38.039 --> 00:03:40.580 It's a heavy one today, but it's a necessary 00:03:40.580 --> 00:03:42.620 one. Absolutely necessary. He's too important 00:03:42.620 --> 00:03:44.659 to be just a footnote. OK, let's drop the needle 00:03:44.659 --> 00:03:47.719 then. Take us back. Who was Lamont Coleman before 00:03:47.719 --> 00:03:50.219 he was a legend? To understand Lamont, you really 00:03:50.219 --> 00:03:52.439 have to understand the geography first. He was 00:03:52.439 --> 00:03:56.219 born May 30, 1974, Harlem, New York City, specifically 00:03:56.219 --> 00:03:58.979 139th Street between Lenox and Fifth Avenue. 00:03:59.139 --> 00:04:02.759 And 1974. I mean, New York is a completely different 00:04:02.759 --> 00:04:05.120 planet back then. It's not the tourist -friendly, 00:04:05.240 --> 00:04:07.919 sanitized Times Square you see today. Oh, not 00:04:07.919 --> 00:04:10.199 at all. It's gritty. It's dangerous, especially 00:04:10.199 --> 00:04:13.020 in certain neighborhoods. But it's also incredibly 00:04:13.020 --> 00:04:15.879 vibrant. It's the incubator for what hip -hop 00:04:15.879 --> 00:04:19.420 is about to become. And Lamont was the baby of 00:04:19.420 --> 00:04:21.639 the family. The youngest of three. The youngest 00:04:21.639 --> 00:04:24.160 of three, yes. His mother was Gilda Terry and 00:04:24.160 --> 00:04:27.560 his father was Charles Davis. But, and this is 00:04:27.560 --> 00:04:29.720 a common story for that era, the father leaves 00:04:29.720 --> 00:04:32.120 the picture very early on while Lamont is still 00:04:32.120 --> 00:04:34.180 a child. So it's essentially a single mother 00:04:34.180 --> 00:04:37.290 household. Mostly, yes. But the real dynamic 00:04:37.290 --> 00:04:39.089 you need to pay attention to is the siblings. 00:04:39.329 --> 00:04:42.269 He grew up with two older half -brothers, Donald 00:04:42.269 --> 00:04:45.430 and Leroy Finazzi. Finazzi. Okay, that name is 00:04:45.430 --> 00:04:47.389 important. And these brothers, they aren't just 00:04:47.389 --> 00:04:49.029 background characters, right? They're not just 00:04:49.029 --> 00:04:51.829 names on a family tree. No, absolutely not. They 00:04:51.829 --> 00:04:53.970 are, in a way, the bookends of his life. One 00:04:53.970 --> 00:04:56.410 of them, Donald, introduces him to the dream 00:04:56.410 --> 00:04:59.230 that will make him a star. And the other, well, 00:04:59.350 --> 00:05:02.370 the other, Leroy, is inextricably tied to the 00:05:02.370 --> 00:05:04.350 nightmare that ends it all. But we'll get there. 00:05:04.649 --> 00:05:07.889 So as a kid, he's little Al. He's Montmont. Just 00:05:07.889 --> 00:05:10.790 a neighborhood kid. Every superhero has an origin 00:05:10.790 --> 00:05:14.110 story. You know, a radioactive spire bite or 00:05:14.110 --> 00:05:17.189 a traumatic event in an alleyway. What was Big 00:05:17.189 --> 00:05:19.889 Al's radioactive spider? It was a ticket stub. 00:05:20.149 --> 00:05:23.750 A ticket stub? Seriously? It was 1981. Lamont 00:05:23.750 --> 00:05:26.089 is just seven years old, and his big brother 00:05:26.089 --> 00:05:29.089 Donald takes him to the Beacon Theater. The Beacon. 00:05:29.230 --> 00:05:31.389 That's a legendary venue on the Upper West Side. 00:05:31.509 --> 00:05:34.540 Who was playing that night? Run DMC. Oh, come 00:05:34.540 --> 00:05:37.540 on. At seven years old, I was eating paste and 00:05:37.540 --> 00:05:39.680 watching cartoons when I was seven. He's at a 00:05:39.680 --> 00:05:42.319 Run DMC concert. Well, Lamont was getting a very 00:05:42.319 --> 00:05:44.480 different kind of education. I mean, try to imagine 00:05:44.480 --> 00:05:47.620 that. It's 1981. Hip -hop is still young. It's 00:05:47.620 --> 00:05:50.459 raw. It's electrifying. And you're a seven -year 00:05:50.459 --> 00:05:53.220 -old kid from Harlem seeing Run DMC and Jam Master 00:05:53.220 --> 00:05:56.000 Jay on stage, controlling a crowd of thousands 00:05:56.000 --> 00:05:58.180 of people with just two turntables and a microphone. 00:05:58.379 --> 00:05:59.959 It must have been like seeing magic for the first 00:05:59.959 --> 00:06:02.449 time. That's exactly how his brother described 00:06:02.449 --> 00:06:04.589 it. Donald said that Lamont didn't just enjoy 00:06:04.589 --> 00:06:07.529 the show, he was awed by it, completely mesmerized. 00:06:07.709 --> 00:06:10.170 It's one thing to see the trick, but it's another 00:06:10.170 --> 00:06:12.649 to want to know how it's done. Precisely. It 00:06:12.649 --> 00:06:15.420 flipped a switch in his brain. Donald said from 00:06:15.420 --> 00:06:18.160 that moment on, Lamont was different. He wasn't 00:06:18.160 --> 00:06:20.139 just passively listening to the music anymore. 00:06:20.319 --> 00:06:23.420 He was studying it. He was deconstructing it, 00:06:23.439 --> 00:06:25.540 trying to figure out the rhyme patterns, the 00:06:25.540 --> 00:06:28.120 cadences. I just love that image. The little 00:06:28.120 --> 00:06:30.139 seven -year -old scholar of rhythm in his bedroom. 00:06:30.300 --> 00:06:33.240 So he starts practicing early. Very early. By 00:06:33.240 --> 00:06:35.459 the time he's 12 years old, he's not just playing 00:06:35.459 --> 00:06:37.980 tag in the streets. He's freestyling with his 00:06:37.980 --> 00:06:41.430 neighbors. He's... Battling people on the block, 00:06:41.629 --> 00:06:45.490 older kids, anyone. And around 1990, he starts 00:06:45.490 --> 00:06:47.790 officially writing his rhymes down. And this 00:06:47.790 --> 00:06:50.389 is where we see the first real sign of his personality 00:06:50.389 --> 00:06:52.970 type, his drive. What do you mean by that? Well, 00:06:52.970 --> 00:06:54.329 he doesn't just want to be good. He wants to 00:06:54.329 --> 00:06:57.430 be organized. He forms a group. He does. In 1990, 00:06:57.629 --> 00:06:59.829 he founded a group called Three the Hard Way. 00:07:00.029 --> 00:07:02.870 Three the Hard Way. That has some very 90s action 00:07:02.870 --> 00:07:05.550 movie energy to it. I love it. It was him, a 00:07:05.550 --> 00:07:08.050 guy named Doc Ream, and another guy named Rodney. 00:07:08.649 --> 00:07:11.370 But the group implodes almost immediately. Ah, 00:07:11.470 --> 00:07:14.310 the classic creative differences. Not even that, 00:07:14.350 --> 00:07:16.430 really. It was a lack of hustle, at least from 00:07:16.430 --> 00:07:18.810 his perspective. The other guys just didn't care 00:07:18.810 --> 00:07:21.069 as much as he did. They treated it like a fun 00:07:21.069 --> 00:07:23.189 hobby on a Friday night. He treated it like it 00:07:23.189 --> 00:07:24.970 was his career already. He was a professional 00:07:24.970 --> 00:07:29.110 at 16. Mentally, yes. So Rodney left. They tried 00:07:29.110 --> 00:07:31.870 to rebrand the remaining duo, him and Doc Ream. 00:07:31.949 --> 00:07:34.589 And what did they call themselves? Two Hard Motherfuckers. 00:07:34.610 --> 00:07:37.579 Okay, very subtle. I like it. A branding consultant's 00:07:37.579 --> 00:07:39.800 nightmare, but I respect the directness. Not 00:07:39.800 --> 00:07:42.500 exactly a radio -friendly name for 1990, no. 00:07:42.699 --> 00:07:45.199 But that group folded, too, for the same reason. 00:07:45.220 --> 00:07:47.319 And I think this is a crucial character moment 00:07:47.319 --> 00:07:50.980 for him. How so? Big L looks around at his friends, 00:07:50.980 --> 00:07:53.399 at the people he came up with, and he has this 00:07:53.399 --> 00:07:56.420 powerful realization. If I wait for anyone else 00:07:56.420 --> 00:07:59.100 to be as hungry as I am, I'm going to starve. 00:07:59.319 --> 00:08:02.480 It's a very profound and kind of lonely realization 00:08:02.480 --> 00:08:05.139 for a teenager to have. It is. So he decides 00:08:05.139 --> 00:08:08.290 to go solo. And he decides to take a massive, 00:08:08.310 --> 00:08:10.310 massive risk. This is the Cinderella moment you 00:08:10.310 --> 00:08:11.990 mentioned at the top of the show. This is my 00:08:11.990 --> 00:08:14.170 favorite part of the story. Because the sheer 00:08:14.170 --> 00:08:17.750 audacity required. I get sweaty palms just thinking 00:08:17.750 --> 00:08:19.790 about doing this. Okay, so it's the summer of 00:08:19.790 --> 00:08:23.399 1990. Picture it. 125th Street in Harlem. There's 00:08:23.399 --> 00:08:26.339 a record shop, Rock and Will's Records, and the 00:08:26.339 --> 00:08:29.339 legendary Lord Finesse is inside, signing autographs 00:08:29.339 --> 00:08:31.160 for his new album. And just for our listeners 00:08:31.160 --> 00:08:34.879 who might not have a PhD in 90s rap hierarchies, 00:08:34.899 --> 00:08:37.919 who is Lord Finesse in the ecosystem at that 00:08:37.919 --> 00:08:40.659 specific time? He is a titan. He's one of the 00:08:40.659 --> 00:08:43.259 most respected lyricists out, a top -tier producer, 00:08:43.539 --> 00:08:46.100 and a key figure in the Bronx and Harlem scene. 00:08:46.639 --> 00:08:49.320 He is, for all intents and purposes, a gatekeeper. 00:08:49.620 --> 00:08:52.669 If Lord Finesse co -signs you, you exist. If 00:08:52.669 --> 00:08:54.370 he ignores you, you might as well be invisible. 00:08:54.690 --> 00:08:56.889 So the scene is set. It's summer in New York, 00:08:56.929 --> 00:08:59.049 so it's probably hot. It's loud. There's a line 00:08:59.049 --> 00:09:01.470 of fans snaking through the store. Everyone is 00:09:01.470 --> 00:09:03.429 probably holding a vinyl record, asking for a 00:09:03.429 --> 00:09:05.629 signature, maybe stammering, I love your work, 00:09:05.690 --> 00:09:08.090 man. Then up to the front of the line walks this 00:09:08.090 --> 00:09:11.610 teenager, Lamont Coleman, 16 years old. He doesn't 00:09:11.610 --> 00:09:13.190 ask for an autograph. He doesn't have a record. 00:09:13.389 --> 00:09:15.610 He looks Lord Finesse right in the eye and asks, 00:09:15.769 --> 00:09:18.470 can I rap for you? See, that is just insane. 00:09:18.970 --> 00:09:21.610 Because usually... Famous rappers hate that. 00:09:21.730 --> 00:09:24.470 It's annoying. Hey, man, listen to my mixtape. 00:09:24.850 --> 00:09:26.909 It's the punchline of a bad joke in hip hop. 00:09:27.289 --> 00:09:29.470 99 times out of 100, the security guard just 00:09:29.470 --> 00:09:31.590 steps in and pushes the kid away. But for some 00:09:31.590 --> 00:09:33.889 reason, maybe it was the look of pure confidence 00:09:33.889 --> 00:09:36.110 in his eye. Maybe finesse was just bored. He 00:09:36.110 --> 00:09:37.789 says, all right, go ahead. Show me what you got. 00:09:38.940 --> 00:09:41.960 And Big Al opens his mouth. And he doesn't stumble. 00:09:42.139 --> 00:09:44.960 He doesn't do some simple nursery rhyme rap. 00:09:45.159 --> 00:09:49.399 He spits a freestyle that is so complex, so full 00:09:49.399 --> 00:09:52.200 of multisyllable rhymes and clever punchlines 00:09:52.200 --> 00:09:54.940 that Finesse doesn't just listen for 10 seconds 00:09:54.940 --> 00:09:57.000 and wave him off. He kept listening. He stopped 00:09:57.000 --> 00:09:59.039 everything. He listened to the whole thing. He 00:09:59.039 --> 00:10:01.200 was so impressed that he exchanged phone numbers 00:10:01.200 --> 00:10:04.159 with the kid right there on the spot. That's 00:10:04.159 --> 00:10:06.639 the modern day equivalent of walking up to Steven 00:10:06.639 --> 00:10:09.539 Spielberg. Pitching a movie idea in a coffee 00:10:09.539 --> 00:10:12.240 shop and walking out with a producer credit. 00:10:13.460 --> 00:10:16.919 This doesn't happen. It really is. And just like 00:10:16.919 --> 00:10:20.179 that, with one freestyle, he's in the game. By 00:10:20.179 --> 00:10:23.779 1991, Lamont Coleman, now officially going by 00:10:23.779 --> 00:10:26.919 Big L, is inducted into Lord Finesse's legendary 00:10:26.919 --> 00:10:29.679 collective, the Diggin' in the Crates crew, or 00:10:29.679 --> 00:10:33.419 DITC. Which is not a small thing. DITC is a super 00:10:33.419 --> 00:10:35.700 group of talent. You've got Finesse, you've got 00:10:35.700 --> 00:10:38.860 Showbiz and AG, Diamond D later on, Fat Joe and 00:10:38.860 --> 00:10:41.759 OC join. He fell in with the absolute heavy hitters 00:10:41.759 --> 00:10:43.840 immediately. And this brings up a really interesting 00:10:43.840 --> 00:10:46.720 point about the barrier to entry in the 90s versus 00:10:46.720 --> 00:10:49.299 today. Oh, it's a huge difference. Today, you 00:10:49.299 --> 00:10:51.539 can just upload a song to SoundCloud or make 00:10:51.539 --> 00:10:54.000 a video for TikTok. If the algorithm likes you, 00:10:54.019 --> 00:10:55.899 you're famous, you don't need anyone's permission. 00:10:56.100 --> 00:10:58.620 You can record a hit song in your bedroom. Exactly. 00:10:58.659 --> 00:11:01.759 But back then... It was gladiatorial. There was 00:11:01.759 --> 00:11:03.919 no internet to hide behind. You couldn't go viral. 00:11:04.139 --> 00:11:06.539 You had to physically stand in front of a gatekeeper, 00:11:06.700 --> 00:11:09.340 a person who knew more than you, who was better 00:11:09.340 --> 00:11:11.620 than you, and prove in real time that you were 00:11:11.620 --> 00:11:13.220 better than everyone else trying to get their 00:11:13.220 --> 00:11:15.539 attention. You had to be undeniable, right then 00:11:15.539 --> 00:11:18.320 and there. No autotune, no second takes, no editing. 00:11:18.669 --> 00:11:21.210 And Big L thrived in that environment. That was 00:11:21.210 --> 00:11:23.389 his element. He went to Julia Richmond High School, 00:11:23.509 --> 00:11:26.769 graduated in 92, but his real education was happening 00:11:26.769 --> 00:11:28.950 in the hallways and on the street corners. He 00:11:28.950 --> 00:11:31.210 said in his last interview, in the beginning, 00:11:31.330 --> 00:11:33.710 all I ever saw me doing was battling everybody 00:11:33.710 --> 00:11:36.029 on the street corners, rhyming in the hallways, 00:11:36.190 --> 00:11:38.570 beating on the wall. It was a sport to him. It 00:11:38.570 --> 00:11:40.370 was his version of playing basketball. It was 00:11:40.370 --> 00:11:42.830 more than a sport. It was combat. And that combat 00:11:42.830 --> 00:11:45.370 mentality is what directly led to the development 00:11:45.370 --> 00:11:48.980 of his specific, unique style. You mentioned 00:11:48.980 --> 00:11:51.379 compounding earlier. Yeah, let's dig into that. 00:11:51.480 --> 00:11:53.740 Because critics and rappers always talk about 00:11:53.740 --> 00:11:56.639 his razor blade flow. What specifically was he 00:11:56.639 --> 00:11:59.440 doing with words that was so different? Because 00:11:59.440 --> 00:12:02.399 to an untrained ear, sometimes rap just sounds 00:12:02.399 --> 00:12:04.620 like rap. Okay, so a very simplified explanation 00:12:04.620 --> 00:12:07.240 is that most rappers at the time, and even most 00:12:07.240 --> 00:12:10.000 rappers now, use what we call end rhymes. You 00:12:10.000 --> 00:12:12.000 say a sentence, and the last word of that sentence 00:12:12.000 --> 00:12:13.899 rhymes with the last word of the next sentence. 00:12:14.120 --> 00:12:18.259 Simple. Cat had that. Simple, effective. I went 00:12:18.259 --> 00:12:20.139 to the store, I wanted to buy some more. Easy 00:12:20.139 --> 00:12:22.940 to follow. Right, it works. But Big L didn't 00:12:22.940 --> 00:12:25.779 do that. He used compounding. He would stack 00:12:25.779 --> 00:12:29.340 internal rhymes, multisyllabic rhymes, and metaphors 00:12:29.340 --> 00:12:32.179 all on top of each other, rapidly, often within 00:12:32.179 --> 00:12:35.299 the same single bar of music. So he's rhyming 00:12:35.299 --> 00:12:36.840 the middle of the sentence with the end of the 00:12:36.840 --> 00:12:39.200 next run, all while setting up a punchline that's 00:12:39.200 --> 00:12:41.289 going to hit you three bars later. So it's like 00:12:41.289 --> 00:12:44.809 he's playing 3D chess with words while everyone 00:12:44.809 --> 00:12:47.070 else is still playing checkers. That's a perfect 00:12:47.070 --> 00:12:49.789 analogy. It's incredibly dense. It's the kind 00:12:49.789 --> 00:12:52.090 of rap you have to rewind the tape three or four 00:12:52.090 --> 00:12:55.230 times just to catch everything he said. Critics 00:12:55.230 --> 00:12:57.289 called it a lyrical snick up. He was basically 00:12:57.289 --> 00:13:00.169 undressing his competition with words. I read 00:13:00.169 --> 00:13:02.409 one review, I think it was from MF DiBella at 00:13:02.409 --> 00:13:05.309 AllMusic, who described his flow as having a 00:13:05.309 --> 00:13:07.970 razor blade under the tongue. That is such a 00:13:07.970 --> 00:13:10.230 vivid and accurate description. It implies that 00:13:10.230 --> 00:13:12.169 if you get too close, if you try to battle him, 00:13:12.230 --> 00:13:14.149 you're going to get cut. And he was cutting people 00:13:14.149 --> 00:13:17.470 left and right. But being that skilled, that, 00:13:17.590 --> 00:13:20.750 I guess, that aggressive with his lyrics, it 00:13:20.750 --> 00:13:23.190 kind of led him into a trap, didn't it? With 00:13:23.190 --> 00:13:26.419 that first single, Devil's Son. It did. This 00:13:26.419 --> 00:13:29.299 is where the story takes a very weird and defining 00:13:29.299 --> 00:13:33.399 turn. This is 1993. He releases a promo single 00:13:33.399 --> 00:13:35.840 called Devil's Son. Now, for people who haven't 00:13:35.840 --> 00:13:38.820 heard this track, it is intense. Intense is a 00:13:38.820 --> 00:13:41.179 very polite word for it. It's graphically violent. 00:13:41.399 --> 00:13:44.440 It's got occult themes. It's basically a slasher 00:13:44.440 --> 00:13:46.440 movie on a beat. It really is. The lyrics are 00:13:46.440 --> 00:13:49.610 shocking, even by today's standards. Was Big 00:13:49.610 --> 00:13:52.389 L a devil worshiper? Was he trying to start some 00:13:52.389 --> 00:13:54.990 kind of satanic cult in Harlem? No, not at all. 00:13:55.049 --> 00:13:57.230 And this is the great misconception that followed 00:13:57.230 --> 00:13:59.269 him for years. He explained it later in interviews. 00:13:59.549 --> 00:14:02.230 He was just a huge fan of horror flicks. He loved 00:14:02.230 --> 00:14:04.649 watching Halloween, Friday the 13th, A Nightmare 00:14:04.649 --> 00:14:07.370 on Elm Street. The classic 80s slashers. Exactly. 00:14:07.529 --> 00:14:09.929 And he looked at his own reality, the very real 00:14:09.929 --> 00:14:12.769 violence he saw in Harlem, the poverty, the desperation. 00:14:13.110 --> 00:14:15.409 And he just combined the two. He said he wanted 00:14:15.409 --> 00:14:17.389 to put it all together in a rhyme. So it was 00:14:17.389 --> 00:14:19.399 cinematic? It was just... another form of storytelling 00:14:19.399 --> 00:14:22.639 for him. It was. But because he was so damn good 00:14:22.639 --> 00:14:25.039 at it, so convincing, the industry looked at 00:14:25.039 --> 00:14:27.919 that one song and said, OK, we know what he is. 00:14:28.019 --> 00:14:31.919 This is the horrorcore guy. Horrorcore. Just 00:14:31.919 --> 00:14:34.659 the name of that subgenre sounds niche and limiting. 00:14:34.779 --> 00:14:37.639 It is. It's a subgenre focused on graphic violence, 00:14:37.879 --> 00:14:41.190 supernatural horror, the macabre. You can think 00:14:41.190 --> 00:14:44.610 of groups like the Gravdegaz or early 3 -6 Mafia. 00:14:44.870 --> 00:14:47.950 Big L inadvertently became a pioneer of a genre 00:14:47.950 --> 00:14:49.570 that he didn't actually want to belong to. It's 00:14:49.570 --> 00:14:51.730 like a brilliant actor who plays a villain just 00:14:51.730 --> 00:14:54.690 one time, but does it so well that nobody will 00:14:54.690 --> 00:14:56.809 ever hire him to play the romantic lead again. 00:14:56.950 --> 00:14:59.509 That is a perfect analogy. He felt completely 00:14:59.509 --> 00:15:01.769 boxed in by it. He wanted a show he could do 00:15:01.769 --> 00:15:03.629 everything. He could make party tracks. He could 00:15:03.629 --> 00:15:06.870 tell stories. He could battle rap. Devil's Son 00:15:06.870 --> 00:15:09.789 cast this long, dark shadow over his early career. 00:15:10.009 --> 00:15:12.370 But he kept grinding. Regardless, he made an 00:15:12.370 --> 00:15:15.769 appearance on Yo! MTV Reps in 92, which was the 00:15:15.769 --> 00:15:18.690 absolute holy grail of exposure for a rapper 00:15:18.690 --> 00:15:21.009 back then. He was on a remix of a Lord Finesse 00:15:21.009 --> 00:15:23.389 track, Yes You May, and he had a standout verse 00:15:23.389 --> 00:15:26.509 on Represent from Showbiz and AG's classic album. 00:15:26.649 --> 00:15:28.230 He was making all the right moves. And then he 00:15:28.230 --> 00:15:30.649 won that amateur freestyle battle hosted by Nubian 00:15:30.649 --> 00:15:32.970 Productions. Yes, that was a huge moment for 00:15:32.970 --> 00:15:35.450 his street credibility. How many people were 00:15:35.450 --> 00:15:37.610 in that battle again? 2 ,000. 2 ,000 contestants. 00:15:37.909 --> 00:15:39.950 And he won the whole thing. He was the last man 00:15:39.950 --> 00:15:42.090 standing. And that just reinforces the level 00:15:42.090 --> 00:15:43.929 of skill we are dealing with here. This wasn't 00:15:43.929 --> 00:15:45.750 hype from his friends. This wasn't a marketing 00:15:45.750 --> 00:15:48.429 gimmick. This was empirical evidence that he 00:15:48.429 --> 00:15:50.509 was the sharpest blade in the entire drawer. 00:15:50.750 --> 00:15:53.490 And all of this momentum, the DITC affiliation, 00:15:53.490 --> 00:15:56.409 the battle wins, it finally led to a major label 00:15:56.409 --> 00:16:00.240 deal with Columbia Records. Signed in 1993. And 00:16:00.240 --> 00:16:02.960 that led to the debut album in March of 1995. 00:16:03.620 --> 00:16:05.860 Lifestyles of Depor and Dangerous. An iconic 00:16:05.860 --> 00:16:08.659 title. An iconic album cover. One of the best 00:16:08.659 --> 00:16:11.259 of the decade. But not iconic sales. Yeah. Not 00:16:11.259 --> 00:16:13.759 even close. No. And this is where the story just 00:16:13.759 --> 00:16:15.700 gets so frustrating. Let's really talk about 00:16:15.700 --> 00:16:18.740 that disconnect. It's 1995. This is a golden 00:16:18.740 --> 00:16:21.389 era. for New York hip -hop. You have Biggie's 00:16:21.389 --> 00:16:24.090 Ready to Die. You have Wu -Tang's 36 Chambers. 00:16:24.110 --> 00:16:26.690 You have Nas' Illmatic. Hip -hop is selling millions 00:16:26.690 --> 00:16:29.429 of records. Why did Big L's debut album come 00:16:29.429 --> 00:16:32.529 out and only hit number 149? That's barely charting. 00:16:32.720 --> 00:16:35.559 It's a mix of a few crucial factors. First and 00:16:35.559 --> 00:16:37.340 foremost, you have to look at the label, Columbia 00:16:37.340 --> 00:16:40.399 Records. They were a massive pop and rock label. 00:16:40.620 --> 00:16:43.340 They knew how to sell a Michael Jackson or a 00:16:43.340 --> 00:16:45.659 Bruce Springsteen record. I honestly don't think 00:16:45.659 --> 00:16:47.980 they had any idea what to do with an artist like 00:16:47.980 --> 00:16:50.519 Big L. So the marketing was just completely off. 00:16:50.700 --> 00:16:52.779 The marketing was practically non -existent for 00:16:52.779 --> 00:16:55.139 the mainstream audience. He wasn't making radio 00:16:55.139 --> 00:16:58.639 friendly hits like Big Papa or Juicy. He was 00:16:58.639 --> 00:17:02.340 making gritty, complex, lyrical. underground 00:17:02.340 --> 00:17:05.509 street rap, the kind of stuff that... ditc was 00:17:05.509 --> 00:17:07.769 famous for the underground loved it though the 00:17:07.769 --> 00:17:10.269 streets knew what it was oh absolutely but in 00:17:10.269 --> 00:17:13.829 1995 if you didn't have a glossy high budget 00:17:13.829 --> 00:17:16.829 video on mtv and heavy rotation and a catchy 00:17:16.829 --> 00:17:19.470 hook sung by an r b singer you weren't moving 00:17:19.470 --> 00:17:21.750 a million units it was just that simple and big 00:17:21.750 --> 00:17:23.710 l wasn't willing to compromise on that was he 00:17:23.710 --> 00:17:25.289 he wasn't going to make that kind of record no 00:17:25.289 --> 00:17:28.009 he was a purist and that's why we respect him 00:17:28.009 --> 00:17:29.789 so much today but it's also why he didn't sell 00:17:29.789 --> 00:17:32.750 back then by the year 2000 five years after its 00:17:32.750 --> 00:17:35.359 release the album had only sold about 200 000 00:17:35.359 --> 00:17:38.279 copies which is respectable for an indie artist 00:17:38.279 --> 00:17:41.619 today but for a major label signee in the cd 00:17:41.619 --> 00:17:44.559 era boom that's a failure in the eyes of the 00:17:44.559 --> 00:17:47.559 executives it's a massive failure and that failure 00:17:47.559 --> 00:17:50.579 led to the inevitable in late 1996 he gets the 00:17:50.579 --> 00:17:52.579 phone call he's been dropped from colombia the 00:17:52.579 --> 00:17:55.180 dreaded artistic differences which is almost 00:17:55.180 --> 00:17:57.500 always just industry code for you didn't make 00:17:57.500 --> 00:18:01.089 us enough money Big L put it a lot more bluntly 00:18:01.089 --> 00:18:03.430 in an interview. He said, I was there with a 00:18:03.430 --> 00:18:05.369 bunch of strangers that didn't really know my 00:18:05.369 --> 00:18:08.130 music. So now he's at a major crossroads. He's 00:18:08.130 --> 00:18:09.970 been to the mountaintop. He was signed to a legendary 00:18:09.970 --> 00:18:13.089 label. And now he's been kicked off. Most rappers 00:18:13.089 --> 00:18:15.349 at that point would just quit. They become bitter, 00:18:15.509 --> 00:18:18.309 fade away, and blame the industry. But Big L 00:18:18.309 --> 00:18:20.529 had that hustler mentality from the streets. 00:18:20.769 --> 00:18:24.480 He didn't complain. He pivoted. In 1998, he founded 00:18:24.480 --> 00:18:26.819 Flamboyant Entertainment. His own independent 00:18:26.819 --> 00:18:29.039 record label. His own label. And listen to his 00:18:29.039 --> 00:18:30.900 business model because it's absolutely brilliant. 00:18:31.119 --> 00:18:33.519 He told the Village Voice in an interview that 00:18:33.519 --> 00:18:35.339 he planned to distribute the kind of hip -hop 00:18:35.339 --> 00:18:38.819 that sold without needing top 40 samples or R 00:18:38.819 --> 00:18:41.140 &B hooks. So he was doubling down on his style. 00:18:41.319 --> 00:18:43.039 He was basically saying, I'm not going to change 00:18:43.039 --> 00:18:45.140 my music to fit the market. I'm going to find 00:18:45.140 --> 00:18:47.210 the market that fits my music. He was creating 00:18:47.210 --> 00:18:49.930 his own lane. And that bet paid off almost immediately 00:18:49.930 --> 00:18:52.190 with one of the most important and ingenious 00:18:52.190 --> 00:18:54.750 songs in hip -hop history. Vap -hop history. 00:18:54.950 --> 00:18:57.990 Oh, man. Ebonics. Criminal slang. If you haven't 00:18:57.990 --> 00:18:59.650 heard this song, you need to pause this deep 00:18:59.650 --> 00:19:02.170 dive right now and go listen to it. It was literally 00:19:02.170 --> 00:19:04.789 a dictionary said to a beat. It is linguistic 00:19:04.789 --> 00:19:07.789 anthropology. It's a master class in code switching. 00:19:08.150 --> 00:19:11.009 He breaks down African -American vernacular English, 00:19:11.130 --> 00:19:14.490 or AAVE slang, term by term, for two and a half 00:19:14.490 --> 00:19:17.109 minutes straight. Brand new car is a new wheel. 00:19:17.369 --> 00:19:19.910 If you're broke, you're on your last meal. Coca 00:19:19.910 --> 00:19:23.549 -Cola is Coke. Crack is rock. The feds is the 00:19:23.549 --> 00:19:26.109 pigs. The joint is the box. It's educational, 00:19:26.230 --> 00:19:29.109 but it also slapped. It was catchy as hell. It 00:19:29.109 --> 00:19:31.609 was pure genius. The Source magazine named it 00:19:31.609 --> 00:19:33.710 one of the top five independent singles of the 00:19:33.710 --> 00:19:36.319 year. The playwright Idris Goodwin later called 00:19:36.319 --> 00:19:38.680 it the best example of L's impressive command 00:19:38.680 --> 00:19:41.140 of the English language. It proved unequivocally 00:19:41.140 --> 00:19:43.460 that he didn't need a major label to make a hit. 00:19:43.559 --> 00:19:45.920 He just needed his voice and a good beat. And 00:19:45.920 --> 00:19:48.279 that independence, that incredible buzz he created 00:19:48.279 --> 00:19:51.299 all on his own from the ground up that attracted 00:19:51.299 --> 00:19:54.000 the Sharks in a good way this time. Enter Damon 00:19:54.000 --> 00:19:57.380 Dash. The co -CEO of Rockefeller Records. And 00:19:57.380 --> 00:19:59.099 we need to really set the context here. What 00:19:59.099 --> 00:20:03.000 is Rockefeller in 1998, early 1999? They are 00:20:03.000 --> 00:20:05.240 the New York Yankees of rap. They are the empire. 00:20:05.700 --> 00:20:08.220 Jay -Z has just released Volume 2, Hard Knock 00:20:08.220 --> 00:20:10.799 Life. The single is a global phenomenon. He's 00:20:10.799 --> 00:20:13.500 not just a rapper anymore. He's a certified superstar. 00:20:14.140 --> 00:20:16.980 And Rockefeller is looking to expand. They want 00:20:16.980 --> 00:20:19.460 to corner the entire market. And Dame Dash sees 00:20:19.460 --> 00:20:22.119 Big L's independent hustle with Ebonics. He sees 00:20:22.119 --> 00:20:25.339 a guy who has the raw, uncut street credibility 00:20:25.339 --> 00:20:28.859 that Jay -Z respects, but also the buds and the 00:20:28.859 --> 00:20:30.799 lyrical talent that can make them even more money. 00:20:30.880 --> 00:20:33.539 He wants to sign him. This is the moment. This 00:20:33.539 --> 00:20:36.680 is the what if. Big L is sitting across the table 00:20:36.680 --> 00:20:39.000 from the hottest, most powerful label in the 00:20:39.000 --> 00:20:41.480 world. He could have just signed on the dotted 00:20:41.480 --> 00:20:43.519 line, taken the check and bought a mansion. He 00:20:43.519 --> 00:20:44.900 could have. It would have been the easy thing 00:20:44.900 --> 00:20:48.660 to do. But he had a condition. And this tells 00:20:48.660 --> 00:20:51.500 you everything you need to know about his heart 00:20:51.500 --> 00:20:54.380 and his loyalty. What was the condition? He insisted 00:20:54.380 --> 00:20:57.279 that his crew, a group he had formed called the 00:20:57.279 --> 00:21:01.140 Wolfpack. It was Irv McGruff, C -Town, and Stan 00:21:01.140 --> 00:21:04.039 Spippe signed to Rockefeller as well. If I eat, 00:21:04.119 --> 00:21:06.579 we all eat. He was bringing his whole team with 00:21:06.579 --> 00:21:08.900 him. Exactly. He wasn't going to leave his friends 00:21:08.900 --> 00:21:10.900 behind in Harlem. He basically told Damon Dash, 00:21:11.039 --> 00:21:12.839 I'm not coming alone. It's all of us or none 00:21:12.839 --> 00:21:15.839 of us. That is such a risky move. Yeah. Usually 00:21:15.839 --> 00:21:17.559 a label in that position of power would just 00:21:17.559 --> 00:21:21.079 say, no thanks. We just want you the star. Usually, 00:21:21.119 --> 00:21:24.779 yes. But Rockefeller wanted Big L so badly that 00:21:24.779 --> 00:21:27.190 they agreed. They were moving forward with signing 00:21:27.190 --> 00:21:29.950 the entire group. And Jay -Z himself confirmed 00:21:29.950 --> 00:21:32.049 this later, right? This isn't just a rumor. No, 00:21:32.089 --> 00:21:35.049 it's a fact. Jay -Z said in an interview, quote, 00:21:35.210 --> 00:21:37.369 we were about to sign him right before he passed 00:21:37.369 --> 00:21:41.009 away. It was a done deal. A done deal. Let's 00:21:41.009 --> 00:21:42.910 just pause for a second and imagine that record 00:21:42.910 --> 00:21:46.130 label roster. You have Jay -Z at the peak of 00:21:46.130 --> 00:21:49.049 his powers. You have Memphis Bleak. You have 00:21:49.049 --> 00:21:52.589 Beanie Siegel. And you add Big L to that lineup. 00:21:52.920 --> 00:21:55.539 It completely changes the entire architecture 00:21:55.539 --> 00:21:58.900 of early 2000s hip hop. Does Big L challenge 00:21:58.900 --> 00:22:01.619 Jay -Z for the throne? Do they become a dual 00:22:01.619 --> 00:22:04.039 superpower like the Steph Curry and Kevin Durant 00:22:04.039 --> 00:22:06.339 of rap and just dominate everything? Or do their 00:22:06.339 --> 00:22:09.660 egos clash? It creates a super team before super 00:22:09.660 --> 00:22:12.319 teams were even a thing in sports. The lyrical 00:22:12.319 --> 00:22:14.259 talent on that label would have been frightening. 00:22:14.480 --> 00:22:16.299 It would have been an arms race that nobody else 00:22:16.299 --> 00:22:17.980 could win. And the contracts were being drawn 00:22:17.980 --> 00:22:20.519 up. The process to sign the whole group officially 00:22:20.519 --> 00:22:23.619 started on February 8th, 1999. February 8th, 00:22:23.619 --> 00:22:25.740 okay. Keep that date in your mind. The pen is 00:22:25.740 --> 00:22:27.640 hovering over the paper. The dream is finally, 00:22:27.700 --> 00:22:30.180 finally happening. And then, one week later, 00:22:30.319 --> 00:22:33.079 February 15th, 1999. We have to go there. 45 00:22:33.079 --> 00:22:35.519 West, 139th Street, right in his own neighborhood. 00:22:35.839 --> 00:22:38.299 It was a drive -by shooting. Big L was walking 00:22:38.299 --> 00:22:41.559 near his home. A car pulls up. He was shot nine 00:22:41.559 --> 00:22:45.220 times. Nine times. In the face and chest. It 00:22:45.220 --> 00:22:48.359 was brutal. It was personal. It was not a robbery 00:22:48.359 --> 00:22:51.039 gone wrong. They didn't take his jewelry, which 00:22:51.039 --> 00:22:52.700 was worth a lot of money. They didn't take his 00:22:52.700 --> 00:22:55.299 wallet. It was a targeted execution. That level 00:22:55.299 --> 00:22:59.980 of violence nine times. That implies hatred. 00:23:00.380 --> 00:23:02.380 That implies they were sending a message. It 00:23:02.380 --> 00:23:04.759 does. It was meant to be a definitive brutal 00:23:04.759 --> 00:23:08.400 end. So immediately the NYPD is involved. Who 00:23:08.400 --> 00:23:11.420 did they look at as the primary suspect? Almost 00:23:11.420 --> 00:23:14.000 immediately, the investigation focused on a childhood 00:23:14.000 --> 00:23:16.319 friend of Lamont Coleman's, a guy named Gerard 00:23:16.319 --> 00:23:18.740 Woodley. A friend? Someone he grew up with? They 00:23:18.740 --> 00:23:20.920 grew up on the same block, but the police theory 00:23:20.920 --> 00:23:23.319 was that this was an act of retaliation. but 00:23:23.319 --> 00:23:25.579 not for something that Big L himself had done. 00:23:25.740 --> 00:23:27.460 This is the part of these stories that's always 00:23:27.460 --> 00:23:30.119 so tragic. The successful artist gets pulled 00:23:30.119 --> 00:23:32.440 down by the people and the problems they were 00:23:32.440 --> 00:23:34.440 trying to escape. The police believed it was 00:23:34.440 --> 00:23:37.259 retaliation for something Big L's older brother, 00:23:37.339 --> 00:23:40.099 Leroy Fenazzi, the one known as Big Lee, had 00:23:40.099 --> 00:23:42.799 done or was believed to have done. So Big L was 00:23:42.799 --> 00:23:45.150 a proxy target. He was killed to send a message 00:23:45.150 --> 00:23:47.210 to his brother. That was the working theory for 00:23:47.210 --> 00:23:49.849 a very long time. We can't get to the brother, 00:23:49.950 --> 00:23:51.890 so we get to the famous rapper. But they did 00:23:51.890 --> 00:23:53.750 arrest Woodley, right? They arrested him three 00:23:53.750 --> 00:23:56.750 months later. But here is the problem with street 00:23:56.750 --> 00:24:01.210 crimes in that era. Evidence. And witnesses. 00:24:02.089 --> 00:24:04.009 People in the neighborhood don't talk to the 00:24:04.009 --> 00:24:06.089 police. Witnesses suddenly can't remember what 00:24:06.089 --> 00:24:08.730 they saw. Woodley was released due to a lack 00:24:08.730 --> 00:24:11.380 of evidence. The case went cold. And it stayed 00:24:11.380 --> 00:24:14.279 cold for a very long time. For years. For decades. 00:24:14.339 --> 00:24:17.359 It was just another unsolved Harlem murder. And 00:24:17.359 --> 00:24:20.319 Gerard Woodley. He didn't exactly get a happy 00:24:20.319 --> 00:24:22.380 ending out of this either. No. What happened 00:24:22.380 --> 00:24:24.559 to him? Gerard Woodley was killed himself in 00:24:24.559 --> 00:24:27.319 2016. Shot in the head in Harlem. Live by the 00:24:27.319 --> 00:24:29.339 sword, die by the sword, I guess. It seems that 00:24:29.339 --> 00:24:33.160 way. And even then, things remained murky. The 00:24:33.160 --> 00:24:35.539 rapper Cameron, who grew up with and knew both 00:24:35.539 --> 00:24:38.319 of them very well, posted a video after Woodley's 00:24:38.319 --> 00:24:40.480 death claiming that Big L had actually attempted 00:24:40.480 --> 00:24:43.460 to have Woodley killed a week before L's own 00:24:43.460 --> 00:24:46.299 death. Wait, what? That turns the entire narrative 00:24:46.299 --> 00:24:48.900 on its head. But that just sounds messy. That 00:24:48.900 --> 00:24:51.440 sounds like street rumors. It is incredibly messy. 00:24:51.519 --> 00:24:53.500 And for a long, long time, that's all it was. 00:24:53.720 --> 00:24:58.700 Rumors, street talk, whispers. Until 2017. 2017. 00:24:59.660 --> 00:25:01.940 A book is published. It's called Epheline, The 00:25:01.940 --> 00:25:05.279 Rise and Fall of the 139th St. NFL Crew. Written 00:25:05.279 --> 00:25:07.740 by an author named Lou Black. And who is Lou 00:25:07.740 --> 00:25:10.099 Black in this story? He was Gerard Woodley's 00:25:10.099 --> 00:25:12.440 cousin. So this isn't a journalist speculating 00:25:12.440 --> 00:25:14.920 from a desk in midtown Manhattan. This is coming 00:25:14.920 --> 00:25:17.480 from inside the circle. This is family business 00:25:17.480 --> 00:25:19.640 being aired out for the world to see. And the 00:25:19.640 --> 00:25:22.339 story this book tells, it's not just a simple 00:25:22.339 --> 00:25:25.579 case of retaliation. It's much more specific 00:25:25.579 --> 00:25:28.569 and much, much darker. It is. The book alleges 00:25:28.569 --> 00:25:30.890 that Big Lee El's brother was in prison at the 00:25:30.890 --> 00:25:33.029 time of these events. And from his prison cell, 00:25:33.190 --> 00:25:35.650 he allegedly hired a hitman to take out Gerard 00:25:35.650 --> 00:25:37.569 Woodley and some of his associates on the street. 00:25:37.710 --> 00:25:39.950 Okay, so the brother, Big Lee, orders a hit from 00:25:39.950 --> 00:25:43.250 jail. Where does Big El fit into this alleged 00:25:43.250 --> 00:25:45.210 plot? This is the part of the story that just 00:25:45.210 --> 00:25:48.049 hurts to read. The allegation in the book is 00:25:48.049 --> 00:25:50.650 that Big El Amant was tasked by his older brother 00:25:50.650 --> 00:25:53.269 with identifying the targets to the hired hitman. 00:25:53.769 --> 00:25:56.750 He was supposed to be the spotter. Oh, wow. So 00:25:56.750 --> 00:25:59.069 in this version of the story, he isn't just an 00:25:59.069 --> 00:26:01.309 innocent bystander caught in the crossfire. He's 00:26:01.309 --> 00:26:03.450 an active participant in the plot. According 00:26:03.450 --> 00:26:06.690 to this account, yes. The story goes that on 00:26:06.690 --> 00:26:09.130 the planned day of the hit, Woodley noticed he 00:26:09.130 --> 00:26:11.630 was being followed and watched. He got spooked 00:26:11.630 --> 00:26:15.069 and the hit failed. But later that day. Woodley 00:26:15.069 --> 00:26:17.950 allegedly saw Big L with the man he recognized 00:26:17.950 --> 00:26:20.250 as the hitman. He put two and two together. He 00:26:20.250 --> 00:26:22.549 connected the dots. Exactly. In that moment, 00:26:22.569 --> 00:26:25.250 he realized, my childhood friend Lamont just 00:26:25.250 --> 00:26:27.589 tried to have me killed for his brother. And 00:26:27.589 --> 00:26:29.710 the implication of the book is? The implication 00:26:29.710 --> 00:26:32.769 is that Big L was killed a week later to prevent 00:26:32.769 --> 00:26:36.150 another attempt on Woodley's life. It was a preemptive 00:26:36.150 --> 00:26:38.640 strike. That is just heartbreaking. Because it 00:26:38.640 --> 00:26:41.539 takes this larger than life legend figure and 00:26:41.539 --> 00:26:44.160 reminds us that he was still a human being, a 00:26:44.160 --> 00:26:46.660 young man living in what was essentially a war 00:26:46.660 --> 00:26:49.890 zone. It complicates the narrative so much. We 00:26:49.890 --> 00:26:53.089 want our heroes to be pure and untouchable. But 00:26:53.089 --> 00:26:56.309 the reality of 139th Street in the 90s didn't 00:26:56.309 --> 00:26:58.289 allow for that kind of purity. He was caught 00:26:58.289 --> 00:27:01.309 between two worlds, the lyrical prodigy world 00:27:01.309 --> 00:27:03.690 where he was about to sign with Jay -Z and the 00:27:03.690 --> 00:27:05.990 violent, unforgiving reality of his family dynamics 00:27:05.990 --> 00:27:08.690 and neighborhood ties. And the ultimate tragedy 00:27:08.690 --> 00:27:11.289 is that he was so close to getting out for good. 00:27:11.789 --> 00:27:14.509 One week. If he signs that deal a week earlier, 00:27:14.690 --> 00:27:17.450 maybe he moves to a mansion in New Jersey. Maybe 00:27:17.450 --> 00:27:19.890 he's on a tour bus in another state. Maybe he's 00:27:19.890 --> 00:27:22.250 alive today and the entire history of modern 00:27:22.250 --> 00:27:25.089 music is different. So Big L is gone in 1999. 00:27:25.450 --> 00:27:28.220 But the weird thing about music is... Sometimes, 00:27:28.279 --> 00:27:30.519 death is just a career move. It sounds incredibly 00:27:30.519 --> 00:27:32.980 cynical to say, but in the music business, it's 00:27:32.980 --> 00:27:35.900 often true. And his posthumous career is almost 00:27:35.900 --> 00:27:38.480 as robust and successful as his living one. In 00:27:38.480 --> 00:27:41.339 August of 2000, his manager, Rich King, managed 00:27:41.339 --> 00:27:43.539 to put together a posthumous album, The Big Picture. 00:27:43.740 --> 00:27:45.460 And just look at the difference in the commercial 00:27:45.460 --> 00:27:48.500 reception. His debut album flopped. The Big Picture. 00:27:48.599 --> 00:27:51.059 It was certified gold. 500 ,000 copies sold. 00:27:51.369 --> 00:27:53.990 It debuted at number 13 on the Billboard 200. 00:27:54.470 --> 00:27:57.829 It had guest features from Tupac, Fat Joe, Big 00:27:57.829 --> 00:28:00.549 Daddy Kane. It was treated like the coronation 00:28:00.549 --> 00:28:03.589 he never got in life. And the single Flamboyant, 00:28:03.670 --> 00:28:06.529 a track he released independently before his 00:28:06.529 --> 00:28:09.109 death, it became a number one hit on the Billboard 00:28:09.109 --> 00:28:11.819 Hot Rap Tracks chart. His only number one single. 00:28:11.900 --> 00:28:14.779 It's a perfect, tragic example of the mainstream 00:28:14.779 --> 00:28:17.480 finally being ready for him just a few years 00:28:17.480 --> 00:28:19.940 too late. And the releases didn't stop there. 00:28:20.299 --> 00:28:23.059 Over the years, we've seen compilations, unruly 00:28:23.059 --> 00:28:26.220 tracks. But let's fast forward to 2025. This 00:28:26.220 --> 00:28:27.740 is where it gets really interesting for our listeners 00:28:27.740 --> 00:28:29.559 who might think the story ended 20 years ago. 00:28:29.660 --> 00:28:32.660 Right. 2025 has been a massive and somewhat controversial 00:28:32.660 --> 00:28:35.779 year for the Big L legacy. In April of 2025, 00:28:36.319 --> 00:28:39.539 Nas announced that his company, Mass Appeal, 00:28:39.599 --> 00:28:42.640 was launching a Legend Has It series to preserve 00:28:42.640 --> 00:28:45.539 the legacies of hip hop icons. And Big L was 00:28:45.539 --> 00:28:47.880 one of the first artists mentioned. Nas is essentially 00:28:47.880 --> 00:28:50.420 curating the legacy. He knows what Big L meant 00:28:50.420 --> 00:28:52.079 to the culture, and he's stepping in to make 00:28:52.079 --> 00:28:54.279 sure it's handled properly. And then on April 00:28:54.279 --> 00:28:58.500 17, 2025, the Coleman family officially confirmed 00:28:58.500 --> 00:29:02.019 a final, definitive album was on the way. It's 00:29:02.019 --> 00:29:05.160 titled Harlem's Finest, Return of the King. And 00:29:05.160 --> 00:29:08.279 it was released on Halloween, October 31, 2025. 00:29:08.700 --> 00:29:10.680 Halloween. That seems very fitting for the guy 00:29:10.680 --> 00:29:12.900 who famously wrote Devil's Son. Very fitting. 00:29:13.059 --> 00:29:15.759 But it hasn't been a completely smooth rollout. 00:29:16.009 --> 00:29:18.289 The family also released a statement explaining 00:29:18.289 --> 00:29:21.190 why a lot of Big L's older songs have been removed 00:29:21.190 --> 00:29:23.349 from streaming services recently. Why is that 00:29:23.349 --> 00:29:26.289 happening? It's the legal nightmare of 90s hip 00:29:26.289 --> 00:29:29.349 hop preservation. Uncleared samples, uncredited 00:29:29.349 --> 00:29:32.069 producers. The music was made in a time when 00:29:32.069 --> 00:29:33.869 you could just grab a piece of a James Brown 00:29:33.869 --> 00:29:36.990 record and loop it. Now, decades later, lawyers 00:29:36.990 --> 00:29:39.069 get involved and things get pulled down. So the 00:29:39.069 --> 00:29:41.329 legacy is literally fighting to stay audible 00:29:41.329 --> 00:29:44.069 in the digital age. It is. But the fact that 00:29:44.069 --> 00:29:46.369 we are getting a new, officially sanctioned album 00:29:46.369 --> 00:29:49.990 in 2025 shows just how hungry the culture still 00:29:49.990 --> 00:29:52.910 is for his voice. His influence hasn't faded. 00:29:53.089 --> 00:29:54.670 And there was supposed to be a documentary, too, 00:29:54.750 --> 00:29:56.869 right? For years, we've heard about Street Struck. 00:29:57.150 --> 00:29:59.950 Yeah, Street Struck, the Big L story. It was 00:29:59.950 --> 00:30:01.990 being directed by a childhood friend, a guy named 00:30:01.990 --> 00:30:05.470 Juz. They announced it way back in 2017, and 00:30:05.470 --> 00:30:07.849 a trailer was released even earlier in 2009. 00:30:08.190 --> 00:30:11.369 But as of 2024, it was still unreleased. It's 00:30:11.369 --> 00:30:13.650 become one of those lost artifacts of hip -hop 00:30:13.650 --> 00:30:16.470 history. Hopefully, with the momentum from the 00:30:16.470 --> 00:30:19.829 2025 album, that project finally sees the light 00:30:19.829 --> 00:30:22.119 of day. Because people need to see the footage. 00:30:22.259 --> 00:30:23.960 They need to see him rapping in the park as a 00:30:23.960 --> 00:30:26.440 teenager to really get it. Absolutely. Because 00:30:26.440 --> 00:30:29.160 when you see him, you realize his peers weren't 00:30:29.160 --> 00:30:32.220 lying or exaggerating about his skill. The legendary 00:30:32.220 --> 00:30:35.480 DJ Funkmaster Flex went on record in 2019 saying 00:30:35.480 --> 00:30:37.940 that Big L was a better lyricist than the notorious 00:30:37.940 --> 00:30:40.880 B .I .G. and Jay -Z. That is an incredibly bold 00:30:40.880 --> 00:30:43.000 statement. In New York City, that's almost blasphemy. 00:30:43.140 --> 00:30:45.339 It is. But he said, I know people will get mad 00:30:45.339 --> 00:30:47.700 at me. But it's the truth. And another elite 00:30:47.700 --> 00:30:50.460 lyricist, Royce Day, 5 '9", said he believed 00:30:50.460 --> 00:30:53.079 L would be a consensus top three rapper of all 00:30:53.079 --> 00:30:55.599 time if he had lived. And the streets that raised 00:30:55.599 --> 00:30:58.359 him, they honored him too. In 2022, they officially 00:30:58.359 --> 00:31:01.539 renamed the corner of 140th and Lenox. Lamont 00:31:01.539 --> 00:31:04.400 Big L Coleman Way. He is literally a part of 00:31:04.400 --> 00:31:06.519 the map of Harlem now. You can't drive through 00:31:06.519 --> 00:31:08.240 that neighborhood without seeing his name. So 00:31:08.240 --> 00:31:12.349 let's zoom out. We have a guy who died tragically 00:31:12.349 --> 00:31:15.890 young, left behind a relatively small body of 00:31:15.890 --> 00:31:18.789 official work, but cast this absolutely giant 00:31:18.789 --> 00:31:21.809 shadow over the genre. What does it all mean? 00:31:22.109 --> 00:31:26.250 What is his ultimate legacy? I think Big L represents 00:31:26.250 --> 00:31:29.829 the ultimate pure MC because he didn't live long 00:31:29.829 --> 00:31:31.609 enough to make a bad album. He didn't live long 00:31:31.609 --> 00:31:35.559 enough to sell out. He didn't do. quirky, awkward 00:31:35.559 --> 00:31:38.839 collaboration with the pop star that aged poorly. 00:31:39.099 --> 00:31:41.420 He is frozen in amber at the peak of his power. 00:31:41.599 --> 00:31:44.720 He is. He is frozen as this hungry, impossibly 00:31:44.720 --> 00:31:46.960 talented phenomenon. In our collective memory, 00:31:47.099 --> 00:31:49.299 he will always be the best rapper in the room, 00:31:49.400 --> 00:31:51.940 the undefeated battle champion. But the tragedy 00:31:51.940 --> 00:31:53.900 is that he was just about to step out of that 00:31:53.900 --> 00:31:56.180 room and onto the world stage. He was leaving 00:31:56.180 --> 00:31:58.559 the local gym to go play in the NBA finals. And 00:31:58.559 --> 00:32:00.420 that leads directly to the provocative question 00:32:00.420 --> 00:32:02.200 I want to leave our listeners with. It's the 00:32:02.200 --> 00:32:04.539 Game of Thrones question of him. All right, let's 00:32:04.539 --> 00:32:07.240 hear it. If Big L signs that Rockefeller deal, 00:32:07.420 --> 00:32:12.059 if he survives February 15th, 1999, how does 00:32:12.059 --> 00:32:14.680 the entire landscape of 2000s hip hop change? 00:32:15.299 --> 00:32:18.599 Does Jay -Z still become the singular, untouchable 00:32:18.599 --> 00:32:21.480 billionaire mogul if he has to share the spotlight 00:32:21.480 --> 00:32:24.319 and the label's resources with a lyricist of 00:32:24.319 --> 00:32:27.319 Big L's caliber? Does Big L become the undisputed 00:32:27.319 --> 00:32:29.940 face of New York rap? Or do they become the greatest 00:32:29.940 --> 00:32:32.460 duo in hip -hop history and push each other to 00:32:32.460 --> 00:32:35.920 even greater heights? Or, on the flip side, do 00:32:35.920 --> 00:32:38.500 their massive talents and egos clash and burn 00:32:38.500 --> 00:32:41.339 the whole empire down? We will never, ever know. 00:32:41.920 --> 00:32:44.759 And that unsolvable mystery is a huge part of 00:32:44.759 --> 00:32:47.640 the legend. A legend that as of October 2025 00:32:47.640 --> 00:32:50.599 is still being written. Indeed. Still being written. 00:32:50.700 --> 00:32:52.579 Thanks for taking this deep dive with us. If 00:32:52.579 --> 00:32:54.480 you haven't, please go check out Lifestyles of 00:32:54.480 --> 00:32:56.880 Dapor and Dangerous. Go listen to Eubonics and 00:32:56.880 --> 00:32:59.299 just appreciate the skill of a true master of 00:32:59.299 --> 00:33:01.059 the craft. And pay attention to the lyrics. You 00:33:01.059 --> 00:33:02.759 might need to rewind a few times to catch everything. 00:33:03.039 --> 00:33:04.819 Always. We'll catch you on the next one. Stay 00:33:04.819 --> 00:33:05.180 curious.