WEBVTT 00:00:00.000 --> 00:00:02.120 Welcome back to The Deep Dive. We take the sources, 00:00:02.399 --> 00:00:04.459 you send us articles, interviews, all that research, 00:00:04.820 --> 00:00:07.059 and we really try to build a strategic picture 00:00:07.059 --> 00:00:09.419 of the people and ideas shaping things around 00:00:09.419 --> 00:00:12.140 us. Today, we're getting into someone, well, 00:00:12.359 --> 00:00:14.619 pretty fascinating in the comedy world. A real 00:00:14.619 --> 00:00:18.000 lightning rod. Anthony Jezelnik. And our goal 00:00:18.000 --> 00:00:20.219 here, really, is to get past just saying, oh, 00:00:20.280 --> 00:00:22.859 he does dark comedy. We want to dig into the 00:00:22.859 --> 00:00:25.179 actual mechanics, you know, the rhetorical tools, 00:00:25.460 --> 00:00:27.719 the career moves, the strategy behind building 00:00:27.719 --> 00:00:31.100 this brand as the guy who just doesn't care. 00:00:31.660 --> 00:00:35.539 Yeah, to deep dive into... A real strategic commitment, 00:00:35.640 --> 00:00:37.359 isn't it? Because when you actually look at his 00:00:37.359 --> 00:00:38.979 work, source by source, he's not just telling 00:00:38.979 --> 00:00:41.320 edgy jokes. He's built this incredibly specific, 00:00:41.700 --> 00:00:44.200 ah, meticulously structured stage persona. And 00:00:44.200 --> 00:00:46.119 the sources really highlight what defines it. 00:00:46.520 --> 00:00:48.679 That ironic misdirection, the non sequiturs, 00:00:48.700 --> 00:00:50.719 he's really biting insults. Livered with that 00:00:50.719 --> 00:00:53.799 super arrogant deadpan thing. Exactly. And crucially, 00:00:53.939 --> 00:00:56.240 this persona that just consistently takes these 00:00:56.240 --> 00:00:58.740 immoral stances on things. What's so interesting, 00:00:58.759 --> 00:01:01.140 I think, is realizing his style isn't just one 00:01:01.140 --> 00:01:03.020 thing. It's like you said, it's calculated. It's 00:01:03.020 --> 00:01:06.540 this mix, almost a cocktail, of different comedy 00:01:06.540 --> 00:01:08.959 genres. That's spot on. That's the calculation. 00:01:09.260 --> 00:01:12.750 The sources point to him pulling from... black 00:01:12.750 --> 00:01:15.230 comedy, shock humor for the themes, obviously, 00:01:15.750 --> 00:01:18.569 but then blending that with the tight structure 00:01:18.569 --> 00:01:20.989 of observational comedy and that deadpan delivery. 00:01:21.010 --> 00:01:23.609 There's more, too. Right. Oh, yeah. He folds 00:01:23.609 --> 00:01:26.730 in the kind of confrontational vibe of insult 00:01:26.730 --> 00:01:28.870 comedy, that awkwardness you get from cringe 00:01:28.870 --> 00:01:31.489 comedy, and even the sort of intellectual step 00:01:31.489 --> 00:01:33.969 back of satire. It's like he doesn't just tell 00:01:33.969 --> 00:01:36.469 a joke. He's deploying this whole complex toolkit. 00:01:36.750 --> 00:01:40.370 OK, so let's trace this back. Where did this 00:01:40.370 --> 00:01:43.769 super technical specific and kind of amoral persona 00:01:43.769 --> 00:01:46.969 actually start, because the roots are maybe not 00:01:46.969 --> 00:01:48.590 what you'd expect. All right, let's unpack this, 00:01:48.689 --> 00:01:50.510 because yeah, the start of this journey for this 00:01:50.510 --> 00:01:54.230 really calculated comic is, well, it seems pretty 00:01:54.230 --> 00:01:56.209 normal on the surface. Grew up the oldest of 00:01:56.209 --> 00:01:59.390 five kids, Catholic family, upper Sinclair, Pennsylvania. 00:02:00.189 --> 00:02:02.560 Seems worlds away from the guy on stage. It really 00:02:02.560 --> 00:02:05.859 does. And that contrast, that friction is probably 00:02:05.859 --> 00:02:07.760 exactly what a comedian needs, right? His dad 00:02:07.760 --> 00:02:11.159 was a lawyer, mom a housewife. It's a very structured 00:02:11.159 --> 00:02:14.919 middle -class scene. Rules, morality, probably 00:02:14.919 --> 00:02:17.439 pretty predictable. So for someone whose whole 00:02:17.439 --> 00:02:20.360 thing becomes about flipping expectations and 00:02:20.360 --> 00:02:24.520 messing with moral norms, having that solid structure 00:02:24.520 --> 00:02:27.060 to kind of push against, that's gold. And the 00:02:27.060 --> 00:02:29.680 sources actually point to this one... really 00:02:29.680 --> 00:02:32.180 key moment, like a light bulb moment, back in 00:02:32.180 --> 00:02:34.680 elementary school. It wasn't just about being 00:02:34.680 --> 00:02:37.139 funny, it was about understanding the power behind 00:02:37.139 --> 00:02:39.780 comedy. Oh yeah, the postcard story. Right. A 00:02:39.780 --> 00:02:41.860 classmate was moving to a town that wasn't seen 00:02:41.860 --> 00:02:44.580 as great, and Jezelnik makes a sarcastic crack 00:02:44.580 --> 00:02:47.020 about sending a postcard to their, you know, 00:02:47.219 --> 00:02:49.379 lesser new address. And the key thing wasn't 00:02:49.379 --> 00:02:51.659 the joke itself, really. It was who laughed. 00:02:51.800 --> 00:02:53.780 The teacher. The teacher laughed. The authority 00:02:53.780 --> 00:02:57.500 figure. And that apparently taught him this fundamental 00:02:57.500 --> 00:02:59.879 rule he kind of built his career on. He put it 00:02:59.879 --> 00:03:02.120 later as realizing, if you're smart enough that 00:03:02.120 --> 00:03:03.979 adults get it, you can get away with anything. 00:03:04.300 --> 00:03:06.759 It's this insight that being clever, having that 00:03:06.759 --> 00:03:08.520 tight structure, it's not just how you make the 00:03:08.520 --> 00:03:11.039 joke funny. It's the shield. It lets the dark 00:03:11.039 --> 00:03:13.240 stuff get through because people almost have 00:03:13.240 --> 00:03:16.259 to admire the construction first before they 00:03:16.259 --> 00:03:18.400 can react to the content. That makes sense. And 00:03:18.400 --> 00:03:20.879 that focus on structure wasn't just random. After 00:03:20.879 --> 00:03:23.139 high school in 97, he goes to Tulane, gets a 00:03:23.139 --> 00:03:25.139 degree in English lit with a business minor finish 00:03:25.139 --> 00:03:28.560 in 2001. That's not exactly the path to stand 00:03:28.560 --> 00:03:30.939 up. No, and that English lit background, I think 00:03:30.939 --> 00:03:32.580 that's absolutely crucial. He wasn't trying to 00:03:32.580 --> 00:03:36.080 be like an improv guy. His first big dream was 00:03:36.080 --> 00:03:38.620 to write the great American novel. Right. So 00:03:38.620 --> 00:03:41.259 he thinks like a writer first. That explains 00:03:41.259 --> 00:03:43.360 the focus on, you know, getting every word right, 00:03:43.659 --> 00:03:46.560 the precision, the super tight, almost mathematical 00:03:46.560 --> 00:03:49.300 structure of his jokes. A Jeselnik joke is like 00:03:49.300 --> 00:03:52.060 a tiny, perfect, dark short story. So when did 00:03:52.060 --> 00:03:54.780 he shift from wanting to write novels? Well, 00:03:54.780 --> 00:03:57.020 during college, he did an internship out in LA. 00:03:57.060 --> 00:04:00.379 Yeah. And that apparently showed him there were 00:04:00.379 --> 00:04:03.500 other avenues for a writer, as he put it. Still 00:04:03.500 --> 00:04:06.159 focused on writing, though, just maybe not fiction. 00:04:06.379 --> 00:04:09.020 And he was in a fraternity too, Alpha Tau Omega. 00:04:09.879 --> 00:04:12.659 Again, seems pretty standard college stuff, kind 00:04:12.659 --> 00:04:14.819 of clashes with the later persona. Totally, and 00:04:14.819 --> 00:04:16.500 then there's that story from his senior year, 00:04:16.639 --> 00:04:19.100 the sort of personal tragedy turned material. 00:04:19.459 --> 00:04:21.720 His girlfriend accidentally burns down his apartment. 00:04:22.120 --> 00:04:24.959 Ouch! Yeah, but it became fodder for his early 00:04:24.959 --> 00:04:27.199 stand -up attempts, which is, you know, a perfect 00:04:27.199 --> 00:04:29.420 little preview of his whole method, stepping 00:04:29.420 --> 00:04:31.959 back from... personal disaster, observing it, 00:04:32.240 --> 00:04:34.639 finding the dark joke in it. So he moves to LA, 00:04:34.720 --> 00:04:37.959 early 2000s, does the classic LA grind thing, 00:04:38.139 --> 00:04:40.379 working at Borders First. Yep, Borders Bookstore. 00:04:40.860 --> 00:04:43.379 And then he finds these comedy workshops, Greg 00:04:43.379 --> 00:04:46.620 Dean's in Santa Monica, and decides to actually 00:04:46.620 --> 00:04:48.620 try stand -up. And how did that first time go? 00:04:48.899 --> 00:04:52.079 Oh, an absolute train wreck, towards a disaster, 00:04:52.220 --> 00:04:54.160 by his own account. He tried doing this impression 00:04:54.160 --> 00:04:57.189 of his dad getting stung by wasps. Physical comedy. 00:04:57.370 --> 00:05:00.329 Broad. Died. Completely died. He said it lasted 00:05:00.329 --> 00:05:02.930 like one minute but felt like ten. Zero laughs. 00:05:03.170 --> 00:05:05.009 Okay, so that failure becomes really important 00:05:05.009 --> 00:05:09.089 then. Hugely important. Because it made him swear 00:05:09.089 --> 00:05:12.050 off physical comedy forever. It wasn't just, 00:05:12.170 --> 00:05:13.870 oh I prefer wordplay. It was like, nope, that's 00:05:13.870 --> 00:05:16.790 not my weapon. His comedy had to succeed purely 00:05:16.790 --> 00:05:20.339 on the words. The structure. the deadpan. He 00:05:20.339 --> 00:05:23.220 basically narrowed his own focus, forcing himself 00:05:23.220 --> 00:05:26.100 to master that linguistic side. So after Borders, 00:05:26.180 --> 00:05:28.959 he gets a job kind of adjacent to the industry. 00:05:29.120 --> 00:05:31.740 Right. Smart move. Worked behind the scenes as 00:05:31.740 --> 00:05:34.120 an accounting clerk for Deadwood. Great show, 00:05:34.339 --> 00:05:37.019 but he's doing the numbers during the day. And 00:05:37.019 --> 00:05:39.279 then hitting open mics at night, honing the act. 00:05:39.620 --> 00:05:41.339 And just to round out that background picture, 00:05:41.439 --> 00:05:44.100 he's of Slovenian descent, identifies an atheist. 00:05:44.969 --> 00:05:47.230 Which you know gives him that necessary distance 00:05:47.230 --> 00:05:49.470 from the Catholic upbringing to really dissect 00:05:49.470 --> 00:05:52.829 faith Morality death without getting personally 00:05:52.829 --> 00:05:54.629 tangled up in it. He can stand outside the thing. 00:05:54.689 --> 00:05:56.990 He's taking apart. Okay, so he's got the writer's 00:05:56.990 --> 00:05:58.790 brain He's ditched the physical stuff. He's all 00:05:58.790 --> 00:06:02.519 in on the words But that specific voice, that 00:06:02.519 --> 00:06:04.899 trademark dark twist that still needed some shaping, 00:06:05.480 --> 00:06:07.139 he talks about influences, right? Yeah. Yeah. 00:06:07.180 --> 00:06:09.220 And the influences he mentions are kind of like 00:06:09.220 --> 00:06:11.639 the recipe for his style. You've got the really 00:06:11.639 --> 00:06:15.079 precise, economical, one -liner guys like Mitch 00:06:15.079 --> 00:06:17.579 Hedberg and Steven Wright. Joke's like a little 00:06:17.579 --> 00:06:19.980 math problem. Right. Very tight structure. Exactly. 00:06:20.439 --> 00:06:24.040 But then you also have the sharper edge, the 00:06:24.040 --> 00:06:26.139 intelligence of Dennis Miller and Sarah Silverman 00:06:26.139 --> 00:06:30.089 people who used observation, but gave it a real 00:06:30.089 --> 00:06:33.170 bite. Sometimes pretty aggressive. But finding 00:06:33.170 --> 00:06:36.649 his own specific thing, that dark twist moment, 00:06:36.889 --> 00:06:38.569 that apparently took a couple of years of grinding 00:06:38.569 --> 00:06:40.750 it out. Yeah, about two years in, he writes this 00:06:40.750 --> 00:06:43.870 joke that's just weird and dark. And the audience 00:06:43.870 --> 00:06:46.290 reaction was so strong, he had this moment of 00:06:46.290 --> 00:06:48.050 clarity, like, OK, this is it. This is the corner 00:06:48.050 --> 00:06:50.069 I need to own. And do we know which joke it was? 00:06:50.209 --> 00:06:52.430 We do. It's the one called My Girlfriend Loves 00:06:52.430 --> 00:06:54.750 to Eat Chocolate. Yeah. It ended up on his first 00:06:54.750 --> 00:06:57.600 album, Shakespeare. And if you break that joke 00:06:57.600 --> 00:07:00.259 down, it's pure jeslinic. It starts relatable 00:07:00.259 --> 00:07:04.160 almost sweet Then there's this bizarre non sequitur 00:07:04.160 --> 00:07:06.920 that just veers into darkness totally unexpected 00:07:06.920 --> 00:07:10.740 and then the punchline lands with absolute deadpan 00:07:10.740 --> 00:07:14.019 seriousness It's the way he delivers the absurd 00:07:14.019 --> 00:07:16.639 that technical precision that lets you laugh 00:07:16.639 --> 00:07:19.759 at the structure Even while you're maybe recoiling 00:07:19.759 --> 00:07:22.040 from the idea itself. Okay, so he finds the voice 00:07:22.220 --> 00:07:24.180 then he needs the right place to sharpen it. 00:07:24.480 --> 00:07:26.779 And that place was the Comedy Cellar in New York. 00:07:27.220 --> 00:07:29.379 Yeah, finding a home base there was huge. They 00:07:29.379 --> 00:07:31.800 apparently gave him earlier sets, which helped 00:07:31.800 --> 00:07:33.860 him juggle things, you know, between L .A. and 00:07:33.860 --> 00:07:36.160 the movie to New York. And the cellar itself 00:07:36.160 --> 00:07:39.019 had a specific vibe, right? Oh, absolutely. It 00:07:39.019 --> 00:07:42.980 was and is famously this intense, crucible, hyper 00:07:42.980 --> 00:07:45.079 -competitive comedians just constantly ripping 00:07:45.079 --> 00:07:47.519 on each other, busting chops, as they say. Sounds 00:07:47.519 --> 00:07:49.660 rough. It required you to be incredibly quick, 00:07:49.920 --> 00:07:52.180 have perfect timing, and basically grow rhino 00:07:52.180 --> 00:07:54.839 skin. All things that fed directly into developing 00:07:54.839 --> 00:07:57.360 that arrogant, insult -heavy part of his stage 00:07:57.360 --> 00:07:59.379 character. He mentioned specific people there 00:07:59.379 --> 00:08:01.399 who were masters of that. Yeah, he pointed to 00:08:01.399 --> 00:08:03.680 guys like Jim Norton, Colin Quinn, Bobby Kelly, 00:08:03.819 --> 00:08:06.220 Keith Robinson. Said they were the best at that 00:08:06.220 --> 00:08:08.560 aggressive, super quick style. He learned the 00:08:08.560 --> 00:08:10.939 rhythm, the cadence, for delivering those sharp 00:08:10.939 --> 00:08:13.339 insults from watching them. Especially in that 00:08:13.339 --> 00:08:15.449 small, intense room. And that boot camp paid 00:08:15.449 --> 00:08:17.629 off pretty quickly then. Seems like it. Yeah. 00:08:17.850 --> 00:08:21.189 By 2009, he gets his Comedy Central presence 00:08:21.189 --> 00:08:23.889 special. Yeah. Big break. That put him on the 00:08:23.889 --> 00:08:25.930 map for the network. Right. And they named him 00:08:25.930 --> 00:08:27.769 one of their breakout comedians that year. Look 00:08:27.769 --> 00:08:31.069 at the list. Nick Kroll, Aziz Ansari, Whitney 00:08:31.069 --> 00:08:33.370 Cummings, Donald Glover. Wow. That's a heavy 00:08:33.370 --> 00:08:35.990 hitting class. Exactly. And he stood out in that 00:08:35.990 --> 00:08:40.669 crowd with his very specific dark stuff. Proved 00:08:40.669 --> 00:08:43.850 it could work. Which leads to the first album 00:08:43.850 --> 00:08:46.850 in 2010 Shakespeare. Yeah Shakespeare even the 00:08:46.850 --> 00:08:48.490 title is a statement, right? It's like you saying 00:08:48.490 --> 00:08:51.190 these short nasty perfectly built jokes. This 00:08:51.190 --> 00:08:53.950 is high art. This is literature It elevates the 00:08:53.950 --> 00:08:55.970 whole project. Okay, this next part feels like 00:08:55.970 --> 00:08:58.610 a really critical moment a strategic fork in 00:08:58.610 --> 00:09:02.169 the road Maybe he lands a job 2009 first season 00:09:02.169 --> 00:09:05.019 of late night with Jimmy Fallon Staff writer. 00:09:05.419 --> 00:09:08.460 And by his own account, this was the dream job 00:09:08.460 --> 00:09:11.059 before stand -up was even the dream. Right. He 00:09:11.059 --> 00:09:12.480 just wanted to be in that writer's room, you 00:09:12.480 --> 00:09:14.539 know. Throw out jokes with people you respected. 00:09:14.740 --> 00:09:17.299 That was the goal. So what was the problem? The 00:09:17.299 --> 00:09:20.519 problem was him. Or rather, the voice he'd spent 00:09:20.519 --> 00:09:23.940 years crafting at the cellar. It was just fundamentally 00:09:23.940 --> 00:09:26.759 incompatible with what Fallon needed for a big 00:09:26.759 --> 00:09:29.620 mainstream network late night show. His pitches 00:09:29.620 --> 00:09:32.940 kept getting rejected. Too dark. Always too dark. 00:09:33.120 --> 00:09:34.940 Is there a specific example of that? Yeah, the 00:09:34.940 --> 00:09:37.220 source has given a perfect one. There was this 00:09:37.220 --> 00:09:39.240 obesity joke he really believed in. He pitched 00:09:39.240 --> 00:09:41.779 it relentlessly every single day for a month, 00:09:41.980 --> 00:09:45.279 apparently. Wow, persistence. Totally. And Fallon 00:09:45.279 --> 00:09:48.440 apparently liked the joke privately, but he wouldn't 00:09:48.440 --> 00:09:51.039 do it on the show. Why? Because Fallon's brand 00:09:51.039 --> 00:09:54.269 is all about being likable, relatable. He was 00:09:54.269 --> 00:09:56.350 worried that joke would alienate obese viewers, 00:09:56.850 --> 00:09:58.529 hurt his connection with that part of the audience. 00:09:58.629 --> 00:10:00.490 Which is the exact opposite of what Jeselnik 00:10:00.490 --> 00:10:02.690 was building. Exactly. It crystallized the whole 00:10:02.690 --> 00:10:07.570 conflict. Fallon needs universal appeal. Jeselnik's 00:10:07.570 --> 00:10:09.970 brand, the one he was developing, required a 00:10:09.970 --> 00:10:12.509 certain level of repulsion, almost. It needed 00:10:12.509 --> 00:10:14.750 him to be willing to not be liked by everyone. 00:10:15.230 --> 00:10:17.690 The persona was designed to push away the very 00:10:17.690 --> 00:10:20.789 people Fallon had to embrace. So the job just 00:10:20.789 --> 00:10:24.309 became... Yeah, he described it as, you know, 00:10:24.549 --> 00:10:26.190 working hard all day, trying to write in this 00:10:26.190 --> 00:10:29.169 voice that wasn't his, feeling constrained, then 00:10:29.169 --> 00:10:30.929 going straight to the Comedy Cellar, having a 00:10:30.929 --> 00:10:32.870 big stiff drink, and finally getting to do his 00:10:32.870 --> 00:10:35.470 act, the dark stuff. It was tearing him in two, 00:10:35.649 --> 00:10:38.309 basically. Professional duty versus artistic 00:10:38.309 --> 00:10:40.789 identity. And that's a key thing for anyone listening, 00:10:41.009 --> 00:10:42.570 right? Choosing your path. Absolutely. Yeah. 00:10:42.730 --> 00:10:45.740 And he made his choice. March 2010, he leaves, 00:10:46.139 --> 00:10:48.779 walks away from the prestige, the dream job, 00:10:49.360 --> 00:10:51.059 and apparently the producers got it immediately. 00:10:51.320 --> 00:10:53.059 They basically told him, we understand you want 00:10:53.059 --> 00:10:55.440 to go be Anthony Jeselnik. He chose the persona, 00:10:55.740 --> 00:10:58.639 the uncompromising voice he'd found over conventional 00:10:58.639 --> 00:11:01.740 success. That's the moment the amoral stage villain 00:11:01.740 --> 00:11:04.000 wasn't just an act. It became his professional 00:11:04.000 --> 00:11:06.799 path. It had to be. So leaving Fallon was this 00:11:06.799 --> 00:11:09.220 huge gamble, right? But the sources show it paid 00:11:09.220 --> 00:11:11.679 off almost immediately, because he pivoted straight 00:11:11.679 --> 00:11:14.500 into the absolute perfect arena for his kind 00:11:14.500 --> 00:11:17.379 of comedy, the Comedy Central Roasts. Oh, right. 00:11:17.379 --> 00:11:19.919 The Roasts. Perfect fit. Totally. He started 00:11:19.919 --> 00:11:22.980 writing for them in 2010. He loved the Roasts, 00:11:23.080 --> 00:11:25.460 called them the Super Bowl of Comedy. So he starts 00:11:25.460 --> 00:11:27.379 as a writer again? Yeah. First wrote for the 00:11:27.379 --> 00:11:29.559 David Hasselhoff Roast. But here's the thing. 00:11:29.720 --> 00:11:33.360 His jokes, even just on paper, were so sharp, 00:11:33.620 --> 00:11:36.679 so distinctly him that the Comedy Central execs 00:11:36.679 --> 00:11:38.720 noticed him. They saw the potential and offered 00:11:38.720 --> 00:11:40.820 him a spot on the dais as a performer. And his 00:11:40.820 --> 00:11:43.340 first one was the Trump roast in 2011. That was 00:11:43.340 --> 00:11:45.820 it. The roast of Donald Trump. And he knew he 00:11:45.820 --> 00:11:48.360 said he knew this is his big shot, his inflection 00:11:48.360 --> 00:11:50.659 point. Why were the roasts so perfect for him? 00:11:50.879 --> 00:11:53.559 Because the entire format demands cruelty and 00:11:53.559 --> 00:11:56.980 arrogance. The audience expects it. It's a controlled 00:11:56.980 --> 00:11:59.799 environment for insults. He didn't have to apologize 00:11:59.799 --> 00:12:02.539 for his material or ease people into it. The 00:12:02.539 --> 00:12:05.580 roast was the context. It perfectly showcased 00:12:05.580 --> 00:12:08.600 his style. And the reaction. Massive. He called 00:12:08.600 --> 00:12:11.519 it one of my favorite moments of my life. Because 00:12:11.519 --> 00:12:13.679 no one knew who I was, and it just really caught 00:12:13.679 --> 00:12:16.200 everybody by surprise. And the next day, my life 00:12:16.200 --> 00:12:18.600 was completely different. Instantaneous jump 00:12:18.600 --> 00:12:22.629 from nobody to viral sensation. basically. Because 00:12:22.629 --> 00:12:25.429 people finally saw the joke construction in its 00:12:25.429 --> 00:12:28.470 purest form. I think so. Before that roast, you 00:12:28.470 --> 00:12:30.809 know, he might headline a club, but maybe half 00:12:30.809 --> 00:12:32.950 the audience wasn't ready for how dark or detached 00:12:32.950 --> 00:12:36.110 he was. After the Trump roast, the crowds got 00:12:36.110 --> 00:12:37.850 bigger, sure. But more importantly, they knew 00:12:37.850 --> 00:12:39.330 what they were getting. They came for gentlemen. 00:12:39.570 --> 00:12:41.870 That let him be even more himself on stage. And 00:12:41.870 --> 00:12:44.429 the network noticed that shift, too. Immediately. 00:12:44.909 --> 00:12:46.710 Comedy Central comes back right after the roast 00:12:46.710 --> 00:12:49.330 and offers him this big three point deal. An 00:12:49.330 --> 00:12:52.049 hour special. commitments for three more roasts 00:12:52.049 --> 00:12:54.490 and a development deal for his own show. That's 00:12:54.490 --> 00:12:56.669 huge. That's basically the network saying, OK, 00:12:57.029 --> 00:12:59.309 we're investing in this specific polarizing thing 00:12:59.309 --> 00:13:03.009 you do. Exactly. It was strategic validation, 00:13:03.789 --> 00:13:06.769 proof that his gamble, leaving Fallon sticking 00:13:06.769 --> 00:13:10.610 to his guns, had worked. And he delivered on 00:13:10.610 --> 00:13:14.240 those roasts, too. Charlie Sheen in 2011, Roseanne 00:13:14.240 --> 00:13:16.679 Barr in 2012. They were just one -offs. They 00:13:16.679 --> 00:13:18.820 were the engine that solidified his transition 00:13:18.820 --> 00:13:21.899 from being a writer who performed to being the 00:13:21.899 --> 00:13:24.399 performer, Anthony Jeselnik. So that development 00:13:24.399 --> 00:13:26.980 deal leads directly to the Jeselnik Offensive. 00:13:27.320 --> 00:13:30.639 His own show on Comedy Central 2013 ran for two 00:13:30.639 --> 00:13:33.960 seasons, 18 episodes, and he was creator, writer, 00:13:34.299 --> 00:13:36.809 executive producer, host. The whole package. 00:13:36.889 --> 00:13:38.889 Full creative control, which was obviously crucial 00:13:38.889 --> 00:13:40.870 for him after the Fallon experience. What was 00:13:40.870 --> 00:13:43.269 the initial idea behind the show? Was it always 00:13:43.269 --> 00:13:45.570 meant to be his specific kind of thing? Well, 00:13:45.610 --> 00:13:47.649 the context is interesting. Comedy Central was 00:13:47.649 --> 00:13:49.330 actually looking for something to potentially 00:13:49.330 --> 00:13:51.769 follow the Colbert Report. They initially thought 00:13:51.769 --> 00:13:53.990 about maybe a four nights a week show, something 00:13:53.990 --> 00:13:56.669 called Midnight, but Jeselnik had a much clearer, 00:13:56.929 --> 00:13:59.710 maybe more defensive vision. His main drive, 00:13:59.730 --> 00:14:02.289 shaped by being shut down at Fallon, was just 00:14:02.289 --> 00:14:04.539 to have a platform for his monologue. A place 00:14:04.539 --> 00:14:06.919 where he could finally tell all those dark jokes 00:14:06.919 --> 00:14:10.100 that network TV wouldn't touch. So he didn't 00:14:10.100 --> 00:14:12.299 want the typical late night format. Interviews, 00:14:12.440 --> 00:14:15.159 sketches. He actively pushed back against it. 00:14:15.440 --> 00:14:17.440 They apparently did a test interview with a celebrity 00:14:17.440 --> 00:14:20.639 for the pilot and he hated it. Said it felt so 00:14:20.639 --> 00:14:23.600 wrong. It just fit me like a bad suit. He knew 00:14:23.600 --> 00:14:26.000 his strength was the crafted joke, not chit chat. 00:14:26.500 --> 00:14:28.860 The show was built around the writing. Which 00:14:28.860 --> 00:14:31.340 brings us to maybe the most talked about moment 00:14:31.340 --> 00:14:35.279 of that show. The cancer segment. Ah, yes. The 00:14:35.279 --> 00:14:37.139 cancer support group segment. Which you wanted 00:14:37.139 --> 00:14:39.379 to put in the first episode. Right. Talk about 00:14:39.379 --> 00:14:42.019 a statement of intent. This was basically the 00:14:42.019 --> 00:14:44.019 ultimate test of his whole comedic philosophy, 00:14:44.059 --> 00:14:46.860 wasn't it? If the joke structure justifies the 00:14:46.860 --> 00:14:49.440 darkness, then doing cancer jokes for cancer 00:14:49.440 --> 00:14:51.740 survivors and leading your series with that, 00:14:51.960 --> 00:14:53.700 I mean, that's throwing down the gauntlet. It's 00:14:53.700 --> 00:14:57.240 basically asking, can pure intentional darkness 00:14:57.240 --> 00:15:00.480 work as intellectual performance art? Exactly. 00:15:00.700 --> 00:15:04.370 And the network. understandably freaked out a 00:15:04.370 --> 00:15:06.690 bit. I bet. He said he had to really fight with 00:15:06.690 --> 00:15:08.850 Comedy Central to put that on the first episode. 00:15:09.509 --> 00:15:11.690 They were worried, you know, that it was just 00:15:11.690 --> 00:15:13.429 too much too soon, it would turn off too many 00:15:13.429 --> 00:15:15.750 people right out of the gate. They wanted to 00:15:15.750 --> 00:15:18.250 like gradually introduce the darkness. But he 00:15:18.250 --> 00:15:21.129 argued against that. Brilliantly, apparently. 00:15:21.909 --> 00:15:25.200 He used comedy history as his defense. He pointed 00:15:25.200 --> 00:15:27.840 to the premiere of Chappelle's show, specifically, 00:15:28.080 --> 00:15:30.840 that really provocative sketch with Clayton Bigsby, 00:15:31.019 --> 00:15:34.679 the blind white supremacist. Ah, okay. Bold comparison. 00:15:34.779 --> 00:15:38.080 His argument was, look, if your show is gonna 00:15:38.080 --> 00:15:40.240 be edgy, if it's gonna push boundaries constantly, 00:15:40.500 --> 00:15:42.299 you have to signal that immediately. You have 00:15:42.299 --> 00:15:44.440 to establish the rules or the lack of rules right 00:15:44.440 --> 00:15:47.080 from the start. And it worked. It worked. The 00:15:47.080 --> 00:15:49.559 sketch opened the first episode, got a lot of 00:15:49.559 --> 00:15:51.919 positive critical buzz, actually. Even got a 00:15:51.919 --> 00:15:55.179 call. from Jay Leno, of all people, praising 00:15:55.179 --> 00:15:57.940 the segment, its bravery, its execution. It really 00:15:57.940 --> 00:16:00.720 cemented his reputation. This guy understands 00:16:00.720 --> 00:16:02.919 the line perfectly, which is exactly why he could 00:16:02.919 --> 00:16:05.279 step over it so deliberately. So while all this 00:16:05.279 --> 00:16:06.779 is happening with the show, he's still doing 00:16:06.779 --> 00:16:09.100 standup specials, too. Oh, yeah. Released his 00:16:09.100 --> 00:16:12.080 second one, Caligula, in 2013. Again, that title 00:16:12.080 --> 00:16:15.340 invoking Roman excess and cruelty. It's all part 00:16:15.340 --> 00:16:18.220 of the package. Yeah. And then by 2015, his profile 00:16:18.220 --> 00:16:20.929 is high enough that NBC taps him. to host Last 00:16:20.929 --> 00:16:23.049 Comic Standing for a season. Which is interesting 00:16:23.049 --> 00:16:25.250 because that's a pretty mainstream gig. Right. 00:16:25.549 --> 00:16:27.639 It showed he could do the broader... hosting 00:16:27.639 --> 00:16:30.379 thing competently. It proved the dark persona 00:16:30.379 --> 00:16:33.259 was a strategic choice, not like the only tool 00:16:33.259 --> 00:16:36.139 he had. OK. So after navigating network TV, the 00:16:36.139 --> 00:16:38.639 next logical step seems to be streaming. Netflix, 00:16:38.820 --> 00:16:40.500 right? Where you can really control the final 00:16:40.500 --> 00:16:42.580 product, no commercial breaks, fewer content 00:16:42.580 --> 00:16:44.620 restrictions. Yes. Netflix became the perfect 00:16:44.620 --> 00:16:47.279 home for his style. Yeah. Longer specials, totally 00:16:47.279 --> 00:16:50.360 uncensored. And his output there has been pretty 00:16:50.360 --> 00:16:51.659 steady. He started with Thoughts and Prayers 00:16:51.659 --> 00:16:55.049 in 2015. Critically acclaimed, but also Different 00:16:55.049 --> 00:16:57.190 for him, structurally. How so? What changed? 00:16:57.909 --> 00:17:00.690 Well, the first chunk, maybe 40 minutes, it's 00:17:00.690 --> 00:17:04.269 classic Jeselnik. Pure, cold, precision -engineered, 00:17:04.329 --> 00:17:07.750 dark jokes. One -liners like daggers. But then, 00:17:07.809 --> 00:17:10.890 the last 20 minutes or so, he pivots. He starts 00:17:10.890 --> 00:17:13.529 telling these personal stories, anecdotes. Some 00:17:13.529 --> 00:17:15.710 of them pretty vulnerable, actually. Really? 00:17:16.009 --> 00:17:18.190 That seems like a big shift away from the detached 00:17:18.190 --> 00:17:21.750 persona. It was huge. Because it kind of humanized 00:17:21.750 --> 00:17:24.650 the monster. He didn't drop the darkness entirely, 00:17:25.130 --> 00:17:27.549 but he gave the audience a peek behind the curtain. 00:17:28.170 --> 00:17:30.349 He talked about his grandmother's funeral, his 00:17:30.349 --> 00:17:32.690 reaction to the Boston Marathon bombing, getting 00:17:32.690 --> 00:17:35.210 the Jeselnik offensive canceled, even the death 00:17:35.210 --> 00:17:37.789 threats he gets. So why do that? Why add that 00:17:37.789 --> 00:17:41.240 personal layer? I think strategically, it grounds 00:17:41.240 --> 00:17:44.839 the preceding darkness. It suggests, maybe, that 00:17:44.839 --> 00:17:47.779 the source material for all that calculated amorality 00:17:47.779 --> 00:17:51.460 actually comes from grappling with real messy 00:17:51.460 --> 00:17:54.359 human stuff. The detachment becomes the coping 00:17:54.359 --> 00:17:57.079 mechanism, the armor. It added this necessary 00:17:57.079 --> 00:17:59.539 depth to what could have seemed like just a two 00:17:59.539 --> 00:18:01.339 -dimensional villain character. That makes sense. 00:18:01.420 --> 00:18:02.980 And he's kept putting out specials on Netflix 00:18:02.980 --> 00:18:06.039 since then. Yep. Fire in the maternity ward in 00:18:06.039 --> 00:18:08.380 2019, and then Bones and All just came out recently, 00:18:08.500 --> 00:18:11.599 end of November 2024. These specials really show 00:18:11.599 --> 00:18:13.940 him sticking to his guns, refining that unique 00:18:13.940 --> 00:18:16.400 joke architecture, even as the cultural landscape 00:18:16.400 --> 00:18:18.720 around comedy keeps shifting. Now, parallel to 00:18:18.720 --> 00:18:20.740 the stand -up, he's had this other massive success, 00:18:20.880 --> 00:18:24.319 right? The podcast. JRVP. Yeah. The Jessalynick 00:18:24.319 --> 00:18:27.400 and Rosenthal Vanity Project. And strategically, 00:18:27.539 --> 00:18:29.519 the podcast is brilliant because it's the complete 00:18:29.519 --> 00:18:32.279 opposite of the stage persona. How did that start? 00:18:32.380 --> 00:18:35.599 It actually began back in 2015 on NFL .com, believe 00:18:35.599 --> 00:18:37.740 it or not. It was RJVP then, the Rosenthal and 00:18:37.740 --> 00:18:39.920 Jessalyn McVanity Project, with his old college 00:18:39.920 --> 00:18:42.319 buddy from Tulane, Greg Rosenthal. So it had 00:18:42.319 --> 00:18:44.660 this sports anchor initially. But the podcast 00:18:44.660 --> 00:18:48.119 is like this release valve. On stage, he's the 00:18:48.119 --> 00:18:50.799 controlled cold villain. On the podcast, he's 00:18:50.799 --> 00:18:53.660 just Anthony. witty, smart, but conversational, 00:18:53.740 --> 00:18:56.660 arguing about sports, news, whatever, with Rosenthal 00:18:56.660 --> 00:18:58.819 and their producer, Erica Tamposi. So when he 00:18:58.819 --> 00:19:00.440 signed that deal with Comedy Central again in 00:19:00.440 --> 00:19:02.799 2018, the podcast came back with him. Yeah, they 00:19:02.799 --> 00:19:04.720 brought it back under the slightly flipped name, 00:19:04.859 --> 00:19:08.119 JRVP, and it's been huge. I mean, hundreds of 00:19:08.119 --> 00:19:10.599 episodes now, over 240 as of earlier this year. 00:19:10.640 --> 00:19:14.359 Wow. And that weekly relaxed format. lets him 00:19:14.359 --> 00:19:16.799 show off his actual personality, his intelligence, 00:19:17.220 --> 00:19:20.420 his humor, without the amoral shield. Which, 00:19:20.619 --> 00:19:23.480 in a way, makes the stage persona seem even more 00:19:23.480 --> 00:19:25.480 like a deliberate, crafted performance when he 00:19:25.480 --> 00:19:27.440 puts it back on. He also did that interview show, 00:19:27.480 --> 00:19:29.960 Good Talk. Right, Good Talk, with Anthony Jesonleik 00:19:29.960 --> 00:19:32.259 in 2019. Six episodes where he interviewed other 00:19:32.259 --> 00:19:35.380 comedians. Using his platform to talk craft, 00:19:35.680 --> 00:19:37.799 which also kind of reinforces his position as 00:19:37.799 --> 00:19:40.359 a comedian's comedian, someone deeply invested 00:19:40.359 --> 00:19:42.099 in the mechanics of joke -telling. So when you 00:19:42.099 --> 00:19:44.430 look at it all together, rigid specials, the 00:19:44.430 --> 00:19:47.369 confrontational TV show, the loose podcast. It's 00:19:47.369 --> 00:19:50.470 like different facets of a very carefully managed 00:19:50.470 --> 00:19:52.490 intellectual brand. I think that's a great way 00:19:52.490 --> 00:19:54.950 to put it. It's sophisticated compartmentalization. 00:19:55.190 --> 00:19:57.950 He keeps the ruthless writer persona separate 00:19:57.950 --> 00:20:02.289 from but also complementary to the engaging conversational 00:20:02.289 --> 00:20:05.450 guy. Hashtag outro. So looking back at this whole 00:20:05.450 --> 00:20:08.599 arc. Going from wanting to write the great American 00:20:08.599 --> 00:20:11.119 novel to becoming, you know, maybe the great 00:20:11.119 --> 00:20:14.000 American dark comedian. It really feels like 00:20:14.000 --> 00:20:16.200 a master class in applying literary discipline 00:20:16.200 --> 00:20:19.160 to stand up. Taking that love of precise language 00:20:19.160 --> 00:20:21.660 and aiming it at the most uncomfortable subjects 00:20:21.660 --> 00:20:24.440 imaginable. Yeah, and understanding crucially 00:20:24.440 --> 00:20:26.859 that the structure itself would be his shield. 00:20:27.210 --> 00:20:29.690 So the big takeaway then for you listening is 00:20:29.690 --> 00:20:31.829 probably that Juzelnik's success really comes 00:20:31.829 --> 00:20:34.809 down to this incredibly disciplined, almost stubborn 00:20:34.809 --> 00:20:38.410 commitment to that specific persona. Absolutely. 00:20:39.109 --> 00:20:41.250 He walked away from the Fallon dream job. He 00:20:41.250 --> 00:20:43.269 fought the network over that cancer segment on 00:20:43.269 --> 00:20:46.029 the offensive because he knew instinctively that 00:20:46.029 --> 00:20:47.970 if he compromised the persona, if he softened 00:20:47.970 --> 00:20:50.069 the edges, the whole thing that calculated cruelty 00:20:50.069 --> 00:20:52.789 that defines his act would just fall apart. That 00:20:52.789 --> 00:20:55.250 commitment is the brand. And yet... Underneath 00:20:55.250 --> 00:20:58.470 the totally detached amoral presentation, we've 00:20:58.470 --> 00:21:01.250 seen the real world anchors, right? The Catholic 00:21:01.250 --> 00:21:03.710 upbringing he pushes against, the long friendship 00:21:03.710 --> 00:21:05.710 with Greg Rosenthal, his relationship with Amy 00:21:05.710 --> 00:21:09.490 Schumer, the subject matter itself, death, religion, 00:21:09.769 --> 00:21:12.049 family. It's all deeply human stuff just delivered 00:21:12.049 --> 00:21:15.289 with that cold, writerly precision. Which brings 00:21:15.289 --> 00:21:17.250 us to maybe a final thought to leave you with. 00:21:17.670 --> 00:21:20.869 His style is all about these super tight, structured 00:21:20.869 --> 00:21:24.150 jokes, often short. punchlines built on these 00:21:24.150 --> 00:21:27.170 amoral, sometimes shocking ideas. So in today's 00:21:27.170 --> 00:21:29.089 world, where sensitivity levels are arguably 00:21:29.089 --> 00:21:31.190 higher, where certain subjects instantly cause 00:21:31.190 --> 00:21:35.289 outrage, does the craft involved, does the obvious 00:21:35.289 --> 00:21:37.450 intelligence and effort poured into constructing 00:21:37.450 --> 00:21:40.069 that joke, the phrasing, the timing, the structure, 00:21:40.589 --> 00:21:42.750 does that meticulous construction itself act 00:21:42.750 --> 00:21:45.599 as a kind of moral defense? regardless of how 00:21:45.599 --> 00:21:47.640 dark the subject is. Is the architecture the 00:21:47.640 --> 00:21:49.680 justification? Yeah, is the sheer quality of 00:21:49.680 --> 00:21:52.380 the build enough to justify the darkness it contains? 00:21:53.140 --> 00:21:54.680 Something to chew on next time you hear a joke 00:21:54.680 --> 00:21:56.640 that makes you laugh. Maybe makes you wince a 00:21:56.640 --> 00:21:57.039 little bit too.