WEBVTT 00:00:00.000 --> 00:00:02.459 Welcome to the Deep Dive. Today we're cracking 00:00:02.459 --> 00:00:05.080 open the career file of someone who feels incredibly 00:00:05.080 --> 00:00:08.859 familiar. Right. You know, almost like a comedic 00:00:08.859 --> 00:00:11.779 wallpaper in a way. Right. But his actual range, 00:00:11.839 --> 00:00:14.199 his professional dexterity, it's kind of hidden 00:00:14.199 --> 00:00:16.620 in plain sight. Yeah, it really is. We're talking 00:00:16.620 --> 00:00:19.339 about Michael Ian Black, a guy who's somehow 00:00:19.339 --> 00:00:22.480 been both super niche and like massively mainstream 00:00:22.480 --> 00:00:26.010 for what? Over three decades now. It's a fantastic 00:00:26.010 --> 00:00:28.269 case study, really. Professional versatility, 00:00:28.429 --> 00:00:30.329 especially in entertainment where careers can 00:00:30.329 --> 00:00:33.329 be so short -lived. Exactly. Black's longevity 00:00:33.329 --> 00:00:37.710 is pretty remarkable. Stretching from that very 00:00:37.710 --> 00:00:41.070 specific anti -humor of the early 90s right up 00:00:41.070 --> 00:00:44.030 to now, doing deep dive podcasts, literary analysis. 00:00:44.170 --> 00:00:47.500 It just defies. Easy labels. Yeah, it really 00:00:47.500 --> 00:00:49.719 does. When you actually map out his whole arc, 00:00:49.759 --> 00:00:53.140 ensemble, sketch guy, film director, famous sock 00:00:53.140 --> 00:00:55.240 puppet voice. Yeah, forget the sock puppet. Never 00:00:55.240 --> 00:00:57.820 forget the sock puppet. And then, you know, writing 00:00:57.820 --> 00:01:01.159 these deeply personal memoirs, you realize he 00:01:01.159 --> 00:01:03.939 hasn't just like survived industry changes. He's 00:01:03.939 --> 00:01:05.840 often been ahead of them or at least leveraged 00:01:05.840 --> 00:01:07.519 them really well. Oh, that's the real puzzle, 00:01:07.579 --> 00:01:10.439 isn't it? How does one creative mind connect 00:01:10.439 --> 00:01:13.099 something like Wet Hot American Summer, that 00:01:13.099 --> 00:01:16.500 specific brand of summer camp satire, with these 00:01:16.500 --> 00:01:19.140 really serious, thoughtful essay collections? 00:01:19.540 --> 00:01:22.700 So our mission today is to unpack all that, look 00:01:22.700 --> 00:01:26.340 at the key collaborations, those surprising side 00:01:26.340 --> 00:01:29.000 gigs, yes, the sock puppet again, and really 00:01:29.000 --> 00:01:31.879 chart that big shift in his writing career. We 00:01:31.879 --> 00:01:34.260 want to give you a clear but really detailed 00:01:34.260 --> 00:01:37.060 picture of how Black managed to stay relevant, 00:01:37.239 --> 00:01:39.370 even deep. been his influence across so many 00:01:39.370 --> 00:01:41.849 different mediums. So let's get into it, starting 00:01:41.849 --> 00:01:44.769 right at the beginning. Okay, so Michael Ian 00:01:44.769 --> 00:01:48.409 Black, born Michael Ian Schwartz, 1971, Chicago, 00:01:48.709 --> 00:01:51.469 Illinois. Okay. But he grew up mostly in Hillsboro 00:01:51.469 --> 00:01:55.530 Township, New Jersey. Family's Jewish. Parents 00:01:55.530 --> 00:01:57.709 were Jill and Robert Schwartz. His dad owned 00:01:57.709 --> 00:02:00.640 a store. His mom was an executive. Pretty standard 00:02:00.640 --> 00:02:02.840 stuff on the surface. Yeah, but the early years 00:02:02.840 --> 00:02:05.719 weren't exactly smooth sailing. There was quite 00:02:05.719 --> 00:02:07.299 a bit of complexity there, and you can almost 00:02:07.299 --> 00:02:09.560 feel how it might have laid the groundwork for 00:02:09.560 --> 00:02:12.000 his later, more serious stuff. Definitely. His 00:02:12.000 --> 00:02:13.879 parents divorced when he was only three. Wow, 00:02:14.060 --> 00:02:17.520 young. Yeah. And shortly after that, his mother, 00:02:17.680 --> 00:02:20.240 Jill, came out as a lesbian. I mean, those are 00:02:20.240 --> 00:02:22.580 major shifts for any kid. Absolutely defining 00:02:22.580 --> 00:02:24.960 moments. And then there's the tragedy surrounding 00:02:24.960 --> 00:02:27.599 his father. Right. The death of his father, Robert, 00:02:27.759 --> 00:02:31.300 was particularly rough. He was only 39. So young. 00:02:31.719 --> 00:02:35.400 Yeah. And the circumstances. The sources suggest 00:02:35.400 --> 00:02:38.259 it was complicated and, frankly, awful. A head 00:02:38.259 --> 00:02:40.300 injury, apparently from assault. Oh, my God. 00:02:40.439 --> 00:02:42.479 And then a fatal allergic reaction during surgery 00:02:42.479 --> 00:02:45.639 afterwards. Gee. That kind of sudden early loss, 00:02:45.840 --> 00:02:48.699 it really does shape a person, and especially 00:02:48.699 --> 00:02:52.659 a comedic voice. You know, it often gives comedians 00:02:52.659 --> 00:02:56.419 maybe the license to explore darker stuff. Mortality, 00:02:56.419 --> 00:02:58.520 pain through humor, which Black definitely does 00:02:58.520 --> 00:03:00.460 later in his memoir. It gives that undercurrent, 00:03:00.520 --> 00:03:02.439 right, that touch of melancholy beneath the snark. 00:03:02.800 --> 00:03:05.020 But before that tragedy, there was performing. 00:03:05.319 --> 00:03:08.560 He went to Stage Door Manor. Ah, yes. The performing 00:03:08.560 --> 00:03:11.340 arts summer camp. That place is legendary, like 00:03:11.340 --> 00:03:13.900 a breeding ground for young talent. He must have 00:03:13.900 --> 00:03:15.460 started building those collaborative muscles 00:03:15.460 --> 00:03:18.020 there. Exactly. Yeah. That's likely where that 00:03:18.020 --> 00:03:20.740 ensemble instinct really started. But, okay, 00:03:20.879 --> 00:03:22.580 before we jump into the famous groups, we have 00:03:22.580 --> 00:03:24.520 to talk about the name. Right. The name change. 00:03:25.099 --> 00:03:27.599 He was born Schwartz. Why Michael Ian Black? 00:03:27.800 --> 00:03:30.419 It seems straightforward when you hear it, but 00:03:30.419 --> 00:03:32.240 it trips people up sometimes when they're looking 00:03:32.240 --> 00:03:34.680 him up. Yeah. It's actually rooted in, well, 00:03:34.759 --> 00:03:38.740 clarity. His birth name, Schwartz, comes from 00:03:38.740 --> 00:03:41.900 the German word Schwartz. It means? Black. Ah, 00:03:42.060 --> 00:03:45.500 okay. Makes sense. So he chose Michael Ian Black 00:03:45.500 --> 00:03:48.099 professionally. basically, to avoid confusion 00:03:48.099 --> 00:03:50.819 with another actor, Mike Schwartz, who was already 00:03:50.819 --> 00:03:53.319 established. So pragmatic, not trying to hide 00:03:53.319 --> 00:03:56.199 his background or anything. Exactly. Just a practical 00:03:56.199 --> 00:03:58.780 move to carve out his own space. But by using 00:03:58.780 --> 00:04:00.960 the translation, he ended up with a name that's 00:04:00.960 --> 00:04:03.780 honestly pretty memorable and distinct. Definitely 00:04:03.780 --> 00:04:06.840 more striking. And speaking of memorable, we 00:04:06.840 --> 00:04:08.800 absolutely have to talk about one of the most 00:04:08.800 --> 00:04:12.080 gloriously absurd early career moments. Oh, I 00:04:12.080 --> 00:04:13.300 know where you're going with this. He was at 00:04:13.300 --> 00:04:18.149 NYU for a bit. But he dropped out. And the reason 00:04:18.149 --> 00:04:21.829 he dropped out of NYU, just peak Michael Ian 00:04:21.829 --> 00:04:23.970 Black, even before we knew who he was. He left 00:04:23.970 --> 00:04:27.329 New York University in 1991, mind you, to play 00:04:27.329 --> 00:04:30.050 Raphael. Yes. In the promotional campaign for 00:04:30.050 --> 00:04:31.949 the Teenage Mutant Ninja Turtles concert tour. 00:04:32.089 --> 00:04:35.290 Just let that sink in. Trading an NYU education 00:04:35.290 --> 00:04:39.079 for a giant rubber turtle suit. Promoting a concert 00:04:39.079 --> 00:04:41.300 based on a cartoon. It's perfect, though. It 00:04:41.300 --> 00:04:43.699 tells you so much about his willingness to just 00:04:43.699 --> 00:04:47.600 embrace the ridiculous, like, prioritize the 00:04:47.600 --> 00:04:50.500 gig no matter how silly over the, you know, sensible 00:04:50.500 --> 00:04:53.480 path. And being comfortable in a costume, performing 00:04:53.480 --> 00:04:56.240 something fundamentally absurd. It connects directly 00:04:56.240 --> 00:04:58.500 to that anti -humor sketch stuff that came next. 00:04:58.660 --> 00:05:00.899 Absolutely. That's the through line. So, yeah, 00:05:00.959 --> 00:05:04.120 the Raphael thing was a weird brief detour. But 00:05:04.120 --> 00:05:07.000 his real comedy foundation, that was built right 00:05:07.000 --> 00:05:09.680 after. With The State. Ah, The State. Okay, so 00:05:09.680 --> 00:05:11.879 critical. You really can't understand a lot of 00:05:11.879 --> 00:05:14.120 modern, quirky, absurd comedy without touching 00:05:14.120 --> 00:05:16.980 on them. What was their specific thing, and where 00:05:16.980 --> 00:05:20.139 did Black fit in? Well, The State hit MTV from 00:05:20.139 --> 00:05:23.620 93 to 95, about 27 episodes, and it felt pretty 00:05:23.620 --> 00:05:26.079 revolutionary at the time, unlike, say, SNL. 00:05:26.240 --> 00:05:28.560 They really leaned into what people now call 00:05:28.560 --> 00:05:30.519 anti -humor. Right, jokes that weren't really 00:05:30.519 --> 00:05:33.339 jokes. Exactly, or bits that just subverted expectations, 00:05:33.660 --> 00:05:37.120 got really repetitive and silly, or just ended. 00:05:37.500 --> 00:05:39.939 No big punchline. And Black wasn't just acting 00:05:39.939 --> 00:05:42.060 in it. The sources are clear. He was a co -creator, 00:05:42.060 --> 00:05:45.240 a writer. That whole environment was about collaboration, 00:05:45.600 --> 00:05:47.920 building these really conceptual bits together. 00:05:48.220 --> 00:05:50.379 So it wasn't like he was a solo stand -up crafting 00:05:50.379 --> 00:05:53.779 a tight five minutes. His foundation was in this 00:05:53.779 --> 00:05:56.699 group dynamic, this collective creation. Totally. 00:05:56.920 --> 00:05:59.000 Which explains why those partnerships lasted 00:05:59.000 --> 00:06:01.600 so long, well after the show itself ended. Yeah, 00:06:01.639 --> 00:06:03.180 the collaborations with Michael Showalter and 00:06:03.180 --> 00:06:05.079 David Wayne especially. That seems like the core 00:06:05.079 --> 00:06:06.899 group. That's the main thread through this. whole 00:06:06.899 --> 00:06:09.240 period right after the state you get viva variety 00:06:09.240 --> 00:06:13.180 in 97 he co -created that wrote for it and appeared 00:06:13.180 --> 00:06:16.939 as johnny blue jeans johnny blue jeans just the 00:06:16.939 --> 00:06:20.160 name is perfect it captures that specific slightly 00:06:20.160 --> 00:06:24.019 surreal heightened reality they did so well absolutely 00:06:24.019 --> 00:06:27.180 yeah and that sensibility got maybe even more 00:06:27.180 --> 00:06:30.240 refined or maybe more concentrated with Stella 00:06:30.240 --> 00:06:33.259 in 2005 on Comedy Central. Right, Stella. That 00:06:33.259 --> 00:06:35.459 was him, Showalter, and Wayne again, based on 00:06:35.459 --> 00:06:37.480 their stage show, right? Yeah, they co -starred, 00:06:37.480 --> 00:06:39.899 co -wrote the 10 episodes. It had this, like... 00:06:40.089 --> 00:06:42.410 intense cult following. People who loved it really 00:06:42.410 --> 00:06:44.529 loved it. But maybe a bit too weird for mainstream 00:06:44.529 --> 00:06:46.930 back then. Probably. It didn't get a second season. 00:06:47.050 --> 00:06:50.449 But even its failure commercially is kind of 00:06:50.449 --> 00:06:53.029 important. It showed how committed those three 00:06:53.029 --> 00:06:56.250 were to their very specific, absurdist thing, 00:06:56.430 --> 00:06:58.790 regardless of whether everyone got it. But the 00:06:58.790 --> 00:07:01.170 project that really cemented their cult status, 00:07:01.350 --> 00:07:04.029 especially on film, has to be Wet Hot American 00:07:04.029 --> 00:07:06.829 Summer. Well, absolutely. 2001, directed by Wayne. 00:07:06.910 --> 00:07:09.360 It basically created a whole subgenre. Totally. 00:07:09.439 --> 00:07:11.839 That whole vibe of adults playing hyper -emotional 00:07:11.839 --> 00:07:14.560 teens at summer camp. Black played McKinley, 00:07:14.600 --> 00:07:17.620 right? One half of that. Memorably odd counselor 00:07:17.620 --> 00:07:20.019 couple. Yes. And his involvement there was key. 00:07:20.360 --> 00:07:21.939 What's interesting, too, is how he kept coming 00:07:21.939 --> 00:07:24.319 back to it. The sources mentioned he reprised 00:07:24.319 --> 00:07:27.040 McKinley for the Netflix prequel and sequel series 00:07:27.040 --> 00:07:29.240 First Day of Camp and Ten Years Later. Which 00:07:29.240 --> 00:07:32.339 just shows how strong that initial creative bond 00:07:32.339 --> 00:07:34.360 was. He could always go back to that state alumni 00:07:34.360 --> 00:07:36.560 network. It was like a home base. A very powerful 00:07:36.560 --> 00:07:38.980 career anchor. Yeah. Sticking with those collaborators 00:07:38.980 --> 00:07:42.399 paid off. OK. So while he's doing all this niche 00:07:42.399 --> 00:07:45.149 specific. kind of low budget absurdist stuff, 00:07:45.310 --> 00:07:49.110 he simultaneously lands this massively mainstream 00:07:49.110 --> 00:07:52.449 gig, like a voice everyone knew from commercial. 00:07:52.589 --> 00:07:56.870 The Pets .com sock puppet. Yes. It's such a bizarre 00:07:56.870 --> 00:07:59.610 juxtaposition. It really is maybe the biggest 00:07:59.610 --> 00:08:02.300 contradiction. in his early career. Yeah. From, 00:08:02.379 --> 00:08:05.420 what, 1998 to 2000, he was the puppeteer and 00:08:05.420 --> 00:08:07.319 the voice. You couldn't escape that puppet during 00:08:07.319 --> 00:08:09.339 the dot -com bubble. Seriously. And then even 00:08:09.339 --> 00:08:11.819 after Pets .com famously crashed and burned, 00:08:11.959 --> 00:08:14.399 he voiced the same puppet for Barnone Insurance, 00:08:14.620 --> 00:08:16.839 I think. Yeah. Okay, but wait, how does that 00:08:16.839 --> 00:08:19.360 fit? Doing this huge corporate mascot voice, 00:08:19.579 --> 00:08:22.480 doesn't that clash with the whole anti -establishment, 00:08:22.480 --> 00:08:25.019 absurdist comedy brand he was building? Seems 00:08:25.019 --> 00:08:27.259 like selling out, maybe. It's a fair question. 00:08:27.870 --> 00:08:30.050 But I think the connection is actually in the 00:08:30.050 --> 00:08:32.149 performance style. How so? Think about the voice. 00:08:32.230 --> 00:08:35.070 Yeah, it was friendly for a commercial, but it 00:08:35.070 --> 00:08:38.929 had that distinct, slightly anxious, always very 00:08:38.929 --> 00:08:41.309 dry delivery. Okay, yeah, I can hear that. It 00:08:41.309 --> 00:08:43.250 wasn't just generic happy voice. Right, it was 00:08:43.250 --> 00:08:46.250 recognizably him. He brought that kind of deadpan, 00:08:46.389 --> 00:08:49.230 almost sardonic energy from the state into this 00:08:49.230 --> 00:08:52.269 super commercial context. He apparently described 00:08:52.269 --> 00:08:57.120 the job later as painful but fun. That sounds 00:08:57.120 --> 00:08:59.159 about right. Which feels like the perfect summary 00:08:59.159 --> 00:09:01.179 for applying, you know, your slightly intellectual 00:09:01.179 --> 00:09:03.820 comedy chops to mass market advertising. It paid 00:09:03.820 --> 00:09:05.500 the bills while he did the weirder stuff. And 00:09:05.500 --> 00:09:08.919 that dry, sardonic persona, that became his ticket 00:09:08.919 --> 00:09:12.539 to real mainstream visibility with VH1. Oh, man. 00:09:12.659 --> 00:09:15.080 I love this series. He was absolutely everywhere. 00:09:15.259 --> 00:09:18.360 He basically defined ironic nostalgia for a generation. 00:09:18.679 --> 00:09:22.220 Totally. He got huge just making these dry, sarcastic, 00:09:22.240 --> 00:09:24.600 sometimes downright mean jokes about like old 00:09:24.600 --> 00:09:26.659 music videos or fashion trends on I Love the 00:09:26.659 --> 00:09:29.340 70s, 80s. 90s new millennium all of them he was 00:09:29.340 --> 00:09:30.879 the king of the talking heads on those shows 00:09:30.879 --> 00:09:33.659 his timing his delivery yeah he just perfectly 00:09:33.659 --> 00:09:35.940 captured that moment of self -aware pop culture 00:09:35.940 --> 00:09:38.240 obsession what's funny though is how he even 00:09:38.240 --> 00:09:40.740 made fun of being on those shows while on them 00:09:40.740 --> 00:09:43.419 he said stuff like he felt doomed to an eternity 00:09:43.419 --> 00:09:45.740 doing the series that's classic black though 00:09:45.740 --> 00:09:47.960 yeah maintaining that slightly detached meta 00:09:47.960 --> 00:09:50.919 commentary yeah even while being incredibly successful 00:09:50.919 --> 00:09:53.580 within the system yeah and he turned the sarcasm 00:09:53.580 --> 00:09:56.450 on himself too The sources point out he'd often 00:09:56.450 --> 00:09:59.230 make self -deprecating jokes about being Jewish 00:09:59.230 --> 00:10:02.330 -American, sometimes kind of leaning into stereotypes, 00:10:02.509 --> 00:10:05.230 ironically. That's a tricky line to walk. Very 00:10:05.230 --> 00:10:08.789 specific comedic tightrope. Yeah. Using irony 00:10:08.789 --> 00:10:11.129 to poke at identity stuff. And while he was doing 00:10:11.129 --> 00:10:12.990 all that commentary, he was still acting in more 00:10:12.990 --> 00:10:15.370 traditional stuff too, right? Like showing he 00:10:15.370 --> 00:10:17.850 had dramatic chops, sort of. Yeah, he kept a 00:10:17.850 --> 00:10:20.710 foot in network TV. He had a big supporting role 00:10:20.710 --> 00:10:24.210 on Ed, that NBC dramedy. Oh yeah, Ed. With Tom 00:10:24.210 --> 00:10:26.669 Cavanaugh. Right. He played Phil Stubbs for like 00:10:26.669 --> 00:10:30.190 83 episodes between 2000 and 2004. That's a long 00:10:30.190 --> 00:10:32.570 run. Yeah. And he hosted the first season of 00:10:32.570 --> 00:10:35.330 that hidden camera show Spy TV on NBC2. Right. 00:10:35.370 --> 00:10:38.940 Right. But 2004. That was a potentially huge 00:10:38.940 --> 00:10:41.019 turning point that didn't happen. It could have 00:10:41.019 --> 00:10:42.740 sent his career in a totally different direction. 00:10:43.000 --> 00:10:45.360 What was that? He was guest hosting The Late 00:10:45.360 --> 00:10:48.200 Late Show on CBS, auditioning for the permanent 00:10:48.200 --> 00:10:50.960 job after Craig Kilbourne left. Oh, wow. I forgot 00:10:50.960 --> 00:10:52.580 about that. He was actually in the running. He 00:10:52.580 --> 00:10:54.759 was a finalist. The job obviously went to Craig 00:10:54.759 --> 00:10:57.080 Ferguson in the end. Imagine that alternate reality. 00:10:57.460 --> 00:10:59.960 If he had gotten The Late Late Show, would he 00:10:59.960 --> 00:11:02.399 have ever become the writer and podcaster he 00:11:02.399 --> 00:11:06.320 is now? The daily grind of late night? Probably 00:11:06.320 --> 00:11:09.279 not. It likely would have consumed all this creative 00:11:09.279 --> 00:11:12.500 energy. So maybe missing out on that gig was 00:11:12.500 --> 00:11:15.059 actually crucial for letting him explore those 00:11:15.059 --> 00:11:17.919 other more personal avenues later on. Yeah, maybe 00:11:17.919 --> 00:11:20.139 a blessing in disguise. Could be. And around 00:11:20.139 --> 00:11:23.100 the same time, he was channeling that dry, competitive 00:11:23.100 --> 00:11:25.480 edge into something totally different again. 00:11:26.200 --> 00:11:29.080 Poker. Celebrity poker. He was actually good, 00:11:29.179 --> 00:11:31.659 wasn't he? Apparently, yeah. Not just showing 00:11:31.659 --> 00:11:33.259 up for the cameras. He was on Celebrity Poker 00:11:33.259 --> 00:11:36.539 Showdown like five times starting in 2003. Played 00:11:36.539 --> 00:11:40.179 for charities, Endeavor House, Maison. Maison, 00:11:40.179 --> 00:11:42.659 the Jewish response to hunger. Okay. And it wasn't 00:11:42.659 --> 00:11:45.019 just a quick appearance. It speaks to a certain 00:11:45.019 --> 00:11:48.480 skill set, right? Patience, reading people, calculating 00:11:48.480 --> 00:11:52.279 odds. That deadpan face he uses in comedy. Probably 00:11:52.279 --> 00:11:54.610 pretty useful at the poker table. A good poker 00:11:54.610 --> 00:11:57.710 face, literally. Exactly. And he did well. Came 00:11:57.710 --> 00:12:01.269 in third in 2006. Won $100 ,000 for his charity. 00:12:01.610 --> 00:12:04.250 Wow, that's significant. Yeah, and he got praise 00:12:04.250 --> 00:12:06.929 not just from the other celebs, but from actual 00:12:06.929 --> 00:12:09.490 poker pros and commentators. Dave Foley, Phil 00:12:09.490 --> 00:12:12.009 Gordon, Phil Helmuth mentioned him. They noted 00:12:12.009 --> 00:12:14.950 his humor, sure, but also his actual skill. It 00:12:14.950 --> 00:12:17.169 kind of hints at that strategic analytical mind 00:12:17.169 --> 00:12:20.190 beneath the comedy. So the mid -2000s, this feels 00:12:20.190 --> 00:12:22.409 like the next really big shift, moving beyond 00:12:22.409 --> 00:12:25.269 just being a performer or writer in a group towards 00:12:25.269 --> 00:12:27.830 being like the singular authorial voice. Yeah. 00:12:28.110 --> 00:12:31.139 First into film directing, but then... maybe 00:12:31.139 --> 00:12:33.940 more significantly, into literary essays and 00:12:33.940 --> 00:12:36.460 memoir. Right. On the film side, he wrote and 00:12:36.460 --> 00:12:39.519 directed Wedding Days in 2006. That starred Jason 00:12:39.519 --> 00:12:42.480 Biggs and Isla Fisher. Directing is a huge leap 00:12:42.480 --> 00:12:44.980 from sketch performing. Managing a whole feature 00:12:44.980 --> 00:12:47.600 film. Totally different skill set. Requires a 00:12:47.600 --> 00:12:50.720 grasp of narrative arc, structure, that ensemble 00:12:50.720 --> 00:12:53.440 work doesn't always demand. And then a year later, 00:12:53.559 --> 00:12:57.860 2007, he co -wrote Run. Fatboy, run with Simon 00:12:57.860 --> 00:13:00.120 Pegg, who also starred. OK, so he's establishing 00:13:00.120 --> 00:13:02.340 himself behind the camera, too. But the writing, 00:13:02.460 --> 00:13:05.779 the books, that feels like where we really started 00:13:05.779 --> 00:13:07.879 to see a different side of him. I agree. That's 00:13:07.879 --> 00:13:09.759 where the personal stuff, the complexity we talked 00:13:09.759 --> 00:13:12.259 about from his early life, the loss, the family 00:13:12.259 --> 00:13:14.600 dynamics really starts to surface and inform 00:13:14.600 --> 00:13:16.879 the work directly. His first big essay collection 00:13:16.879 --> 00:13:20.700 was My Custom Van, right? In 2008. And 50 other 00:13:20.700 --> 00:13:24.159 mind -blowing essays. But the books after that 00:13:24.159 --> 00:13:26.500 got even deeper, more personal. You're not doing 00:13:26.500 --> 00:13:29.500 it right. Tales of Marriage, Sex, Death, and 00:13:29.500 --> 00:13:32.240 Other Humiliations in 2012. Great title. Isn't 00:13:32.240 --> 00:13:35.019 it? And then Naval Gazing in 2016. Just the titles 00:13:35.019 --> 00:13:36.899 tell you something's changed. She's using that 00:13:36.899 --> 00:13:39.240 comedic toolkit, the timing, the exaggeration, 00:13:39.259 --> 00:13:41.960 but applying it to really serious stuff. Marriage, 00:13:42.200 --> 00:13:45.259 death, just feeling inadequate. How did he manage 00:13:45.259 --> 00:13:47.440 that transition without it feeling, I don't know, 00:13:47.480 --> 00:13:50.179 jarring? overly sentimental. I think it's the 00:13:50.179 --> 00:13:52.600 way he uses that familiar sarcastic voice as 00:13:52.600 --> 00:13:55.519 kind of a shield. But the vulnerability underneath 00:13:55.519 --> 00:14:00.460 feels real. His whole memoir persona is built 00:14:00.460 --> 00:14:02.840 around willingly exploring his own flaws and 00:14:02.840 --> 00:14:05.460 failures. He plays this character of this sort 00:14:05.460 --> 00:14:09.500 of hapless modern guy just trying to figure things 00:14:09.500 --> 00:14:14.899 out. Marriage, fatherhood. Like his VH1 persona, 00:14:14.960 --> 00:14:17.379 but aimed inward. Exactly. The target of the 00:14:17.379 --> 00:14:20.679 satire becomes himself, his own anxieties, and 00:14:20.679 --> 00:14:22.679 that balance, that tension between the detached 00:14:22.679 --> 00:14:26.350 wit and the painful honesty. That's what makes 00:14:26.350 --> 00:14:27.929 those books work, I think. And he wasn't just 00:14:27.929 --> 00:14:30.409 doing books. He started writing for like legit 00:14:30.409 --> 00:14:33.009 literary places, too. McSweeney's. Yep. He has 00:14:33.009 --> 00:14:34.730 a column there called Michael Ian Black is a 00:14:34.730 --> 00:14:37.190 very famous celebrity. Perfect title. So meta. 00:14:37.450 --> 00:14:39.169 Totally. And he's written for the New Yorker 00:14:39.169 --> 00:14:41.309 Shouts and Murmurs section. Like that piece during 00:14:41.309 --> 00:14:43.730 the pandemic, a pandemic college essay that probably 00:14:43.730 --> 00:14:46.350 won't get you into Brown. Those pieces are important, 00:14:46.490 --> 00:14:48.470 though. They show him being accepted into that 00:14:48.470 --> 00:14:51.730 world of contemporary literary humor. He's using 00:14:51.730 --> 00:14:53.789 his fame, sure, but the writing holds up. He's 00:14:53.789 --> 00:14:56.529 not just a comedian dabbling. And he tackled 00:14:56.529 --> 00:14:58.730 politics pretty head on, too. Yeah, that road 00:14:58.730 --> 00:15:01.269 trip book with Meghan McCain. Right. America, 00:15:01.350 --> 00:15:05.750 you sexy bitch. A love letter to freedom. 2012, 00:15:05.950 --> 00:15:08.169 what was the deal with that? It was kind of a 00:15:08.169 --> 00:15:11.179 performance piece in itself. He and McCain drove 00:15:11.179 --> 00:15:13.740 across the country together in 2011. The whole 00:15:13.740 --> 00:15:16.679 idea was putting this, you know, sarcastic, liberal 00:15:16.679 --> 00:15:19.840 Jewish comedian next to a very prominent young 00:15:19.840 --> 00:15:22.659 conservative voice. Polar opposites. And just 00:15:22.659 --> 00:15:24.340 documenting what they found, how people were 00:15:24.340 --> 00:15:26.799 living and thinking in this really polarized 00:15:26.799 --> 00:15:29.360 post -recession moment. It's kind of a fascinating 00:15:29.360 --> 00:15:32.259 artifact using his platform to try and bridge 00:15:32.259 --> 00:15:34.840 that divide or at least observe it honestly while 00:15:34.840 --> 00:15:36.659 still keeping that comedic distance. OK, but 00:15:36.659 --> 00:15:39.440 maybe the weirdest, most unexpected turn in this. 00:15:39.500 --> 00:15:42.740 whole writing phase is that he became a massively 00:15:42.740 --> 00:15:45.279 successful children's author. Isn't that wild? 00:15:45.480 --> 00:15:47.759 How does the guy writing about death and humiliation 00:15:47.759 --> 00:15:50.980 also write books for toddlers? It's a totally 00:15:50.980 --> 00:15:54.000 separate parallel track and he's genuinely great 00:15:54.000 --> 00:15:56.879 at it. His first one was Chicken Cheeks in 2009. 00:15:57.659 --> 00:15:59.940 And it wasn't just some celebrity cash -in. It 00:15:59.940 --> 00:16:02.320 got really good reviews. Kirkus gave it a starred 00:16:02.320 --> 00:16:04.600 review, called it a perfect collaboration of 00:16:04.600 --> 00:16:07.620 text and illustration. Wow. Okay. So legit skills 00:16:07.620 --> 00:16:09.799 in that area, too. Yeah. It shows he understands 00:16:09.799 --> 00:16:13.259 language at its most fundamental level. And he 00:16:13.259 --> 00:16:16.419 kept doing it. A purple kangaroo? A pig parade? 00:16:17.100 --> 00:16:20.460 Is a terrible idea. Naked. Just a whole bunch 00:16:20.460 --> 00:16:22.500 of them. He seems genuinely prolific in that 00:16:22.500 --> 00:16:24.360 space. Absolutely. And then blending the two 00:16:24.360 --> 00:16:26.980 worlds, there was a child's first book of Trump 00:16:26.980 --> 00:16:29.799 in 2016. Oh, right. That one made some waves. 00:16:29.879 --> 00:16:32.059 Yeah. It perfectly combined his newfound ability 00:16:32.059 --> 00:16:34.919 to write simply and engagingly for kids with 00:16:34.919 --> 00:16:37.879 his established satirical political edge using 00:16:37.879 --> 00:16:40.509 that innocent. picture book format to land the 00:16:40.509 --> 00:16:42.269 pretty pointed commentary. It's like he took 00:16:42.269 --> 00:16:44.029 all that understanding of Tony. He honed in sketch 00:16:44.029 --> 00:16:46.330 comedy and just applied it masterfully to everything. 00:16:46.730 --> 00:16:48.769 Essays, political journalism, kids books about 00:16:48.769 --> 00:16:51.049 pigs. OK, so we're moving into the more recent 00:16:51.049 --> 00:16:56.309 era, the rise of digital media podcasts. Established 00:16:56.309 --> 00:16:58.950 comedians had to adapt, find new ways to connect. 00:16:59.330 --> 00:17:02.590 And Black seems like he was pretty early in figuring 00:17:02.590 --> 00:17:05.549 out audio. He definitely was. Podcasting let 00:17:05.549 --> 00:17:07.950 him tap back into that collaborative improvisational 00:17:07.950 --> 00:17:10.569 style, but also eventually build this whole other 00:17:10.569 --> 00:17:12.890 solo, more intellectual thing. How did it start? 00:17:13.390 --> 00:17:16.109 Pretty simply, actually. Leveraging old connections. 00:17:16.309 --> 00:17:19.470 In 2010, he launched Mike and Tom Eat Snacks. 00:17:19.609 --> 00:17:22.190 Was Tom Cavanaugh his co -star from Head? Exactly. 00:17:22.569 --> 00:17:26.009 Pure, fun, low stakes improv comedy. Just them 00:17:26.009 --> 00:17:28.849 riffing on snacks. Classic podcast premise. Totally. 00:17:29.210 --> 00:17:31.789 Then in 2013, he teamed up with Michael Showalter 00:17:31.789 --> 00:17:34.210 again for topics back to the state roots, keeping 00:17:34.210 --> 00:17:36.130 that creative partnership alive in a new format. 00:17:36.250 --> 00:17:38.369 So those first couple of podcasts were kind of 00:17:38.369 --> 00:17:40.910 familiar territory, loose, funny, conversational. 00:17:40.990 --> 00:17:43.650 But the really interesting turn, I think, especially 00:17:43.650 --> 00:17:46.029 for understanding his evolution, is how to be 00:17:46.029 --> 00:17:49.740 amazing. Yes. That's the big one. How to Be Amazing 00:17:49.740 --> 00:17:52.319 is where you really see his intellectual curiosity 00:17:52.319 --> 00:17:56.180 take center stage in this era. It's a serious, 00:17:56.200 --> 00:17:58.099 in -depth interview show. He produces it with 00:17:58.099 --> 00:18:00.720 Jennifer Brennan and Mary Shimkin. And he's good 00:18:00.720 --> 00:18:02.920 at it. Like, transitioning from comedian making 00:18:02.920 --> 00:18:05.220 jokes to actually conducting a thoughtful interview, 00:18:05.380 --> 00:18:07.579 that's not an easy switch. It's rare, but he 00:18:07.579 --> 00:18:10.480 pulls it off. He manages to transform that dry, 00:18:10.859 --> 00:18:13.920 slightly detached persona into something that's 00:18:13.920 --> 00:18:16.779 actually quite probing and insightful as a host. 00:18:16.940 --> 00:18:19.099 He really listens and draws people out. And he 00:18:19.099 --> 00:18:21.119 gets big guests too, right? I remember hearing 00:18:21.119 --> 00:18:23.509 about him interviewing Katy Perry. Yeah. That 00:18:23.509 --> 00:18:25.750 was for her big livestream marathon thing back 00:18:25.750 --> 00:18:28.950 in 2017, Katy Perry Live, Witness Worldwide. 00:18:29.089 --> 00:18:31.009 That shows you the kind of credibility he built 00:18:31.009 --> 00:18:32.910 across different fields. He wasn't just seen 00:18:32.910 --> 00:18:35.750 as the comedy guy. Okay, so How to Be Amazing 00:18:35.750 --> 00:18:38.109 shows his breadth as an interviewer. But then, 00:18:38.190 --> 00:18:42.029 then there's Obscure. Ah, Obscure with Michael 00:18:42.029 --> 00:18:44.609 Ian Black. This one is maybe the most surprising, 00:18:44.750 --> 00:18:46.650 intellectually ambitious thing he's done. It's 00:18:46.650 --> 00:18:49.430 such a wild concept, he just reads classic literature. 00:18:50.309 --> 00:18:54.160 Aloud. Launched in 2018. He reads dense, classic 00:18:54.160 --> 00:18:57.059 novels aloud, chapter by chapter, and then provides 00:18:57.059 --> 00:18:59.579 commentary and analysis. It's like turning Cliff's 00:18:59.579 --> 00:19:01.539 notes into performance art, almost. But with 00:19:01.539 --> 00:19:04.259 really difficult books. Oh, yeah. He did not 00:19:04.259 --> 00:19:06.559 pick easy ones. Season one was Thomas Hardy's 00:19:06.559 --> 00:19:09.539 Jude the Obscure. Which is famously long and 00:19:09.539 --> 00:19:14.240 bleak. Extremely bleak. Season two was Mary Shelley's 00:19:14.240 --> 00:19:16.900 Frankenstein. Season three, Emily brought these 00:19:16.900 --> 00:19:19.640 weathering heights. These are challenging, complex 00:19:19.640 --> 00:19:22.859 19th century texts. So how does he make that 00:19:22.859 --> 00:19:27.039 listenable? Entertaining. He uses all his comedic 00:19:27.039 --> 00:19:29.019 tools, the timing, the self -deprecation, the 00:19:29.019 --> 00:19:31.279 dry delivery, but applies them to the analysis. 00:19:31.519 --> 00:19:34.680 He makes it accessible, relatable, kind of demystifies 00:19:34.680 --> 00:19:36.539 these intimidating classics without dumbing them 00:19:36.539 --> 00:19:39.079 down. So he's basically performing literary criticism 00:19:39.079 --> 00:19:41.980 but making it engaging, using the fame he got 00:19:41.980 --> 00:19:44.240 from, you know, Wet Hot American Summer and sock 00:19:44.240 --> 00:19:46.160 puppets to get people interested in Thomas Hardy. 00:19:46.319 --> 00:19:49.799 Pretty much. It's this incredible leap. It requires 00:19:49.799 --> 00:19:53.539 serious reading. Serious thought, sustained focus. 00:19:53.640 --> 00:19:56.460 It really confirms that intellectual capacity 00:19:56.460 --> 00:19:59.839 that maybe you saw glimpses of in the poker playing 00:19:59.839 --> 00:20:02.559 or the memoir writing. The detached comedy guy, 00:20:02.700 --> 00:20:05.599 that's a persona. Underneath, there's real curiosity. 00:20:06.140 --> 00:20:08.339 But he didn't totally abandon TV comedy while 00:20:08.339 --> 00:20:10.700 doing all this highbrow podcasting. Oh, definitely 00:20:10.700 --> 00:20:13.640 not. He stayed very active. He starred as Bill 00:20:13.640 --> 00:20:15.940 Tundell, the clueless host in that great web 00:20:15.940 --> 00:20:18.960 series Burning Love. Which was such a brilliant 00:20:18.960 --> 00:20:22.000 spoof of The Bachelor. It was so good. And he 00:20:22.000 --> 00:20:25.000 created, wrote, and starred in that bizarre... 00:20:25.279 --> 00:20:28.279 Adult Swim infomercial parody, Your Hole. Played 00:20:28.279 --> 00:20:30.880 that character, Randall Tyree Manderson. Very 00:20:30.880 --> 00:20:33.339 weird, very specific stuff. Exactly. And he did 00:20:33.339 --> 00:20:34.920 great character work elsewhere, too, who was 00:20:34.920 --> 00:20:38.079 Peepers, the super uptight butler on Comedy Central's 00:20:38.079 --> 00:20:40.319 Another Period. Right, for like 30 episodes. 00:20:40.339 --> 00:20:42.799 He was fantastic in that. And then bringing things 00:20:42.799 --> 00:20:46.220 full circle in a way, when Reno 911 came back 00:20:46.220 --> 00:20:49.160 for its reboot in 2020, he had a recurring role 00:20:49.160 --> 00:20:51.579 as Captain Schwartz. Wait, Schwartz using his 00:20:51.579 --> 00:20:54.599 birth name? Deliberately. Playing the commander 00:20:54.599 --> 00:20:58.039 of this militarized parody of Hatzla, the Jewish 00:20:58.039 --> 00:21:00.200 volunteer ambulance service. It was this great 00:21:00.200 --> 00:21:02.460 little nod back to his roots, his identity. That's 00:21:02.460 --> 00:21:05.160 fantastic. And now he's doing new satire. Yeah. 00:21:05.680 --> 00:21:09.140 Brings us right up to today. Since 2024, he's 00:21:09.140 --> 00:21:11.119 been a regular panelist on the U .S. version 00:21:11.119 --> 00:21:13.779 of Have I Got News For You on CNN. With Roy Wood 00:21:13.779 --> 00:21:16.740 Jr. hosting and Amber Ruffin. Right. It feels 00:21:16.740 --> 00:21:18.759 like the perfect culmination in a way, that political 00:21:18.759 --> 00:21:21.940 commentary interest, the dry wit from the VH1 00:21:21.940 --> 00:21:24.660 days, the analytical skills from the literary 00:21:24.660 --> 00:21:27.619 stuff, all coming together for a sharp, timely 00:21:27.619 --> 00:21:30.259 political satire. OK, so just to round out the 00:21:30.259 --> 00:21:33.779 picture of this incredibly varied career. A little 00:21:33.779 --> 00:21:35.240 bit about his personal life. It seems pretty 00:21:35.240 --> 00:21:37.500 stable compared to the professional zigzags. 00:21:37.539 --> 00:21:39.859 Relatively, yeah. He married Martha Ann Hagen 00:21:39.859 --> 00:21:42.319 way back in 1998. That long -term relationship 00:21:42.319 --> 00:21:44.680 seems to be the bedrock. Obviously provided a 00:21:44.680 --> 00:21:46.579 lot of the material for his writing about marriage 00:21:46.579 --> 00:21:48.240 and domestic life. Right, and they have kids. 00:21:48.440 --> 00:21:51.119 Two kids, Elijah, born 2001, and Ruthie, born 00:21:51.119 --> 00:21:53.400 2003. And the family lives in Savannah, Georgia 00:21:53.400 --> 00:21:57.049 now. Interesting choice. The guy who built a 00:21:57.049 --> 00:21:59.710 career partly on dissecting and satirizing American 00:21:59.710 --> 00:22:02.890 culture settles down in one of its most historic 00:22:02.890 --> 00:22:05.130 traditional cities. There's probably an essay 00:22:05.130 --> 00:22:08.109 in that somewhere. Probably. And one last detail, 00:22:08.269 --> 00:22:10.910 kind of a subtle one, about his worldview. Something 00:22:10.910 --> 00:22:13.210 about a philosophical shift. Yeah, it's nuanced, 00:22:13.210 --> 00:22:15.170 but the sources mention it. He apparently used 00:22:15.170 --> 00:22:17.630 to identify as an atheist. Yeah. Pretty firm 00:22:17.630 --> 00:22:20.390 non -believer. Okay. But more recently, he's 00:22:20.390 --> 00:22:23.430 described himself as shifting towards being a 00:22:23.430 --> 00:22:27.140 reluctant... Reluctant deist. That phrase itself 00:22:27.140 --> 00:22:30.440 feels very Michael Ian Black. Doesn't it? It 00:22:30.440 --> 00:22:33.859 suggests moving away from like absolute certainty 00:22:33.859 --> 00:22:36.480 or outright rejection towards something more 00:22:36.480 --> 00:22:39.420 like contemplation. Yeah. A grudging acceptance 00:22:39.420 --> 00:22:41.960 maybe of some kind of unknowable force or order. 00:22:42.079 --> 00:22:45.259 Yeah. Skeptical but open. Exactly. And it feels 00:22:45.259 --> 00:22:48.269 like it mirrors his career in a way. Moving from 00:22:48.269 --> 00:22:50.849 that pure, chaotic, almost nihilistic anti -humor 00:22:50.849 --> 00:22:53.269 of the early days towards this more reflective, 00:22:53.369 --> 00:22:55.789 analytical, deeply engaged intellectual life 00:22:55.789 --> 00:22:57.970 where he's actively grappling with big questions, 00:22:58.049 --> 00:23:01.910 even if he's still wary of easy answers. So when 00:23:01.910 --> 00:23:04.529 you lay it all out like that, Michael Ian Black's 00:23:04.529 --> 00:23:09.269 career, it's not some smooth climb. It's this 00:23:09.269 --> 00:23:12.730 brilliant. kind of amazing strategy of constant 00:23:12.730 --> 00:23:15.990 reinvention constant diversification i mean think 00:23:15.990 --> 00:23:17.690 about the sheer range of contradictions we've 00:23:17.690 --> 00:23:20.190 covered dropping out of nyu for a ninja turtle 00:23:20.190 --> 00:23:23.009 gig still amazing the surreal silliness of wet 00:23:23.009 --> 00:23:26.150 hot american summer then directing movies writing 00:23:26.150 --> 00:23:28.829 these soul -bearing memoirs and now you know 00:23:28.829 --> 00:23:31.630 seriously analyzing 19th century novels like 00:23:31.630 --> 00:23:34.509 jude the obscure on a podcast he created the 00:23:34.509 --> 00:23:36.470 big takeaway i think and maybe what resonates 00:23:36.470 --> 00:23:38.809 most for you listening is just how vital adaptation 00:23:38.809 --> 00:23:41.390 is especially in entertainment today. Black is 00:23:41.390 --> 00:23:43.730 kind of a masterclass in it. How so? He shows 00:23:43.730 --> 00:23:45.769 how you can leverage its specific comedic brand, 00:23:45.970 --> 00:23:48.670 that dry wit, that perfect timing, but use it 00:23:48.670 --> 00:23:51.150 to explore real intellectual depth. He stayed 00:23:51.150 --> 00:23:53.349 relevant not by sticking to one thing, but by 00:23:53.349 --> 00:23:56.390 moving so fluidly between, you know, lowbrow 00:23:56.390 --> 00:23:58.589 sketch and highbrow literature, commercial voice 00:23:58.589 --> 00:24:01.769 work and political kids books. His career. basically 00:24:01.769 --> 00:24:03.809 proves that the skills you pick up in something 00:24:03.809 --> 00:24:06.750 like ensemble, comedy, observation, collaboration, 00:24:07.190 --> 00:24:09.789 finding your voice, can actually translate into 00:24:09.789 --> 00:24:12.549 almost any creative or intellectual field if 00:24:12.549 --> 00:24:14.509 you're willing to stretch. Which leads us to 00:24:14.509 --> 00:24:16.210 our final thought, something for you to chew 00:24:16.210 --> 00:24:19.109 on. We've seen him do comedy, memoir, political 00:24:19.109 --> 00:24:22.450 writing, literary analysis, all successfully. 00:24:22.690 --> 00:24:25.210 So what does it really say about how we define 00:24:25.210 --> 00:24:28.690 celebrity now? When an artist can use the fame 00:24:28.690 --> 00:24:31.490 they got from being funny, from satire, even 00:24:31.490 --> 00:24:34.769 from absurdity as a launching pad to drive real, 00:24:34.930 --> 00:24:37.549 deep, knowledgeable engagement with complex sources, 00:24:37.670 --> 00:24:39.529 whether that's interviewing a guest thoughtfully 00:24:39.529 --> 00:24:42.730 or unpacking a dense Victorian novel. What does 00:24:42.730 --> 00:24:44.250 that model mean for the future of entertainment? 00:24:44.289 --> 00:24:46.849 That's not just entertaining, but genuinely informative 00:24:46.849 --> 00:24:47.970 and insightful, too.