WEBVTT 00:00:00.000 --> 00:00:02.580 Welcome to the Deep Dive, where we take a massive 00:00:02.580 --> 00:00:05.759 stack of sources, articles, interviews, and deep 00:00:05.759 --> 00:00:08.720 research and give you the fast track to being 00:00:08.720 --> 00:00:11.339 the most informed person in the room. Uh -huh. 00:00:11.519 --> 00:00:14.220 Today, we're undertaking a deep dive into a career 00:00:14.220 --> 00:00:17.239 that serves as, well, kind of a blueprint for 00:00:17.239 --> 00:00:19.940 the modern comedic polymath, Jennifer Ann Kirkman. 00:00:20.199 --> 00:00:22.339 Yeah, it's more than just a path, isn't it? It's 00:00:22.339 --> 00:00:24.980 really a masterclass in professional transmutation, 00:00:25.300 --> 00:00:27.879 you could say. Transmutation, I like that. Jen 00:00:27.879 --> 00:00:30.420 Kirkman, she successfully navigated the whole 00:00:30.420 --> 00:00:33.219 high -stakes world of stand -up, you know. Then 00:00:33.219 --> 00:00:35.820 mastered the volatile field of television writing. 00:00:36.060 --> 00:00:39.039 Which is notoriously tough. Exactly. Then crossed 00:00:39.039 --> 00:00:40.880 over to become a New York Times bestselling author 00:00:40.880 --> 00:00:43.679 and then sort of circled back to lend her technical 00:00:43.679 --> 00:00:46.679 comedic expertise as a consultant on prestige 00:00:46.679 --> 00:00:49.140 television, no less. Right. And when you look 00:00:49.140 --> 00:00:51.229 at her public... Most people probably know her 00:00:51.229 --> 00:00:53.929 from, well, two main things, right? Being that 00:00:53.929 --> 00:00:57.189 regular, super quick roundtable panelist on Chelsea 00:00:57.189 --> 00:01:00.770 lately. She did, what, 70 episodes over six years? 00:01:00.890 --> 00:01:04.569 Yeah, a huge run. And of course, her incredibly 00:01:04.569 --> 00:01:07.329 unique and frankly, unforgettable appearances 00:01:07.329 --> 00:01:09.450 narrating on Drunk History. Absolutely. Those 00:01:09.450 --> 00:01:12.390 are iconic. But what's truly fascinating and 00:01:12.390 --> 00:01:16.500 what we're trying to unpack today is the. architectural 00:01:16.500 --> 00:01:19.780 complexity of that career. Okay. While her stand 00:01:19.780 --> 00:01:22.319 -up always remained the core skill, you know, 00:01:22.340 --> 00:01:24.459 the professional infrastructure she built around 00:01:24.459 --> 00:01:27.219 it demanded skills far beyond just performing. 00:01:27.400 --> 00:01:29.519 Like what specifically? Well, ranging from the 00:01:29.519 --> 00:01:31.819 foundational training she got in acting way back 00:01:31.819 --> 00:01:35.159 to her more recent, quite technical role -writing 00:01:35.159 --> 00:01:38.159 -specific, period -appropriate stand -up punchlines 00:01:38.159 --> 00:01:42.340 for a character on The Marvelous Mrs. Maisel. 00:01:42.680 --> 00:01:44.099 That's a really interesting point, the range 00:01:44.099 --> 00:01:46.879 there. It is. So our mission today is to really 00:01:46.879 --> 00:01:49.340 analyze exactly how she leveraged that singular, 00:01:49.500 --> 00:01:52.659 observational, comedic voice across such diverse 00:01:52.659 --> 00:01:54.579 and sometimes kind of contradictory platforms. 00:01:54.859 --> 00:01:57.019 Yeah, turning personal vulnerability into published 00:01:57.019 --> 00:02:00.260 success and technical expertise, it's quite the 00:02:00.260 --> 00:02:01.819 journey. Okay, let's start at the beginning then, 00:02:01.879 --> 00:02:04.299 the origin story. Jennifer Ann Kirkman, born 00:02:04.299 --> 00:02:07.640 August 28, 1974, Needham, Massachusetts. Yep, 00:02:07.739 --> 00:02:10.819 youngest of three sisters. And the sources mention 00:02:10.819 --> 00:02:13.780 her heritage is actually quite diverse. German, 00:02:14.000 --> 00:02:17.740 Polish, French -Canadian, English, you know, 00:02:17.759 --> 00:02:20.180 deep New England roots. Right. But you mentioned 00:02:20.180 --> 00:02:22.360 something earlier that feels more critical to 00:02:22.360 --> 00:02:25.500 her professional delivery. Yeah, absolutely. 00:02:25.759 --> 00:02:28.939 It's her college training. She didn't study English 00:02:28.939 --> 00:02:31.099 or communications, which you might expect. She 00:02:31.099 --> 00:02:33.979 majored in acting at Emerson College in Boston. 00:02:34.139 --> 00:02:37.080 Oh, okay. And that foundational training in performance 00:02:37.080 --> 00:02:39.599 and theatrical presence, that's really crucial, 00:02:39.719 --> 00:02:41.960 I think. How so? How does that acting background 00:02:41.960 --> 00:02:44.180 specifically, you know, show up in her stand 00:02:44.180 --> 00:02:46.659 -up style later on? Well, it provides precision. 00:02:46.819 --> 00:02:48.719 Stand -up, especially the kind Kirkman does, 00:02:48.800 --> 00:02:51.520 that deeply observational personal style, it 00:02:51.520 --> 00:02:54.000 relies heavily on characterization, on vocal 00:02:54.000 --> 00:02:56.699 control. The Emerson training, it means her delivery 00:02:56.699 --> 00:03:00.770 is often less, maybe... aggressive, and more 00:03:00.770 --> 00:03:03.530 finely tuned to emotional nuance compared to 00:03:03.530 --> 00:03:05.669 comics who just came up purely through open mics. 00:03:05.770 --> 00:03:08.330 Right, I see that. It helps her connect the emotional 00:03:08.330 --> 00:03:10.889 core of her material, you know, the sadness, 00:03:10.969 --> 00:03:13.349 the anxiety, with the comedic timing needed for 00:03:13.349 --> 00:03:16.330 the punchline. That precision, it definitely 00:03:16.330 --> 00:03:19.150 allowed her to move pretty seamlessly into later 00:03:19.150 --> 00:03:21.789 voice work and even scripted roles. Makes sense. 00:03:21.909 --> 00:03:24.310 And her stand -up presence itself. That started 00:03:24.310 --> 00:03:26.979 relatively early. Active since 97. Yes, since 00:03:26.979 --> 00:03:29.659 1997. And once she moved out to Los Angeles, 00:03:29.919 --> 00:03:32.479 she like immediately planted herself in those 00:03:32.479 --> 00:03:35.759 key performance hubs, the ones defining that 00:03:35.759 --> 00:03:38.539 whole burgeoning alt comedy scene at the time. 00:03:38.659 --> 00:03:40.580 OK, so which venues are we talking about? Well, 00:03:40.639 --> 00:03:42.419 yeah, the distinction is kind of important. We're 00:03:42.419 --> 00:03:44.599 talking regular spots at the Hollywood Improv 00:03:44.599 --> 00:03:47.780 and the Laugh Factory, you know, the traditional 00:03:47.780 --> 00:03:50.819 club circuit. But also the alternative, more 00:03:50.819 --> 00:03:54.080 narrative focused places like Largo and the Upright 00:03:54.080 --> 00:04:10.289 Citizens Brigade. And she wasn't just working 00:04:10.289 --> 00:04:12.530 solo in these rooms. She was collaborating pretty 00:04:12.530 --> 00:04:15.009 quickly with people who became huge names. Oh 00:04:15.009 --> 00:04:18.040 yeah, right away. The sources track her performing 00:04:18.040 --> 00:04:21.040 with major figures who basically define this 00:04:21.040 --> 00:04:23.939 modern era of comedy. People like Maria Bamford, 00:04:24.079 --> 00:04:27.759 Mike Birbiglia. Wow. And crucially, Chelsea Handler. 00:04:27.899 --> 00:04:30.350 Okay, that Handler connection feels key. It was 00:04:30.350 --> 00:04:32.790 absolutely career defining. It went from just 00:04:32.790 --> 00:04:34.870 working the same rooms to actually performing 00:04:34.870 --> 00:04:38.009 on the Comedians of Chelsea Lately Tour, both 00:04:38.009 --> 00:04:41.110 in 2009 and 2010. Right. This integration, it 00:04:41.110 --> 00:04:43.089 meant she wasn't just some opening act anymore. 00:04:43.149 --> 00:04:45.209 She was being marketed as part of a recognized, 00:04:45.610 --> 00:04:48.529 established comedic brand. That gave her consistent 00:04:48.529 --> 00:04:50.930 visibility that, honestly, many rising comics 00:04:50.930 --> 00:04:52.850 just don't get. Now, here's something that seems 00:04:52.850 --> 00:04:55.959 like an early indicator of her. Maybe strategic 00:04:55.959 --> 00:04:59.120 thinking. And that community focus long before 00:04:59.120 --> 00:05:02.540 she was a bestseller. In 2001, she co -founded 00:05:02.540 --> 00:05:05.699 GirlComic .net with Becky Donahue. Yes. And this 00:05:05.699 --> 00:05:08.459 was very early for that kind of targeted digital 00:05:08.459 --> 00:05:10.560 community building. This is pioneering, right? 00:05:10.699 --> 00:05:13.459 Totally pioneering. And it speaks directly to 00:05:13.459 --> 00:05:15.639 her like mission driven approach. Even back then, 00:05:15.720 --> 00:05:18.740 the intention was specific. Encourage girls and 00:05:18.740 --> 00:05:21.319 women to write funny stories. And importantly, 00:05:21.439 --> 00:05:25.800 to actively combat the... Pretty pervasive sexism 00:05:25.800 --> 00:05:27.759 that really characterized a lot of the club comedy 00:05:27.759 --> 00:05:30.639 environment at the time. So an intentional effort 00:05:30.639 --> 00:05:33.800 to showcase and elevate female voices. Exactly. 00:05:33.800 --> 00:05:35.699 And they backed it up with credibility, too, 00:05:35.759 --> 00:05:38.639 didn't they? Interviewing established, pioneering 00:05:38.639 --> 00:05:41.459 female comics. Yeah, big names like Joy Behar, 00:05:41.759 --> 00:05:45.920 Amy Poehler. Sarah Silverman. Wow. Precisely. 00:05:45.920 --> 00:05:48.259 They were creating this kind of positive reinforcement 00:05:48.259 --> 00:05:51.000 loop. And, you know, while the mission was focused 00:05:51.000 --> 00:05:52.860 on women's perspectives, the sources do confirm 00:05:52.860 --> 00:05:55.040 they included men on the site, too. OK. So it 00:05:55.040 --> 00:05:56.959 was about inclusion and encouragement, not really 00:05:56.959 --> 00:05:59.420 exclusion. But if it was such a pivotal mission 00:05:59.420 --> 00:06:02.220 driven idea, why did it eventually fade away? 00:06:02.339 --> 00:06:05.300 The update stopped in 2003 and the whole site 00:06:05.300 --> 00:06:08.329 closed in 2006. What happened there? Well, that 00:06:08.329 --> 00:06:10.149 short lifespan is actually pretty instructive, 00:06:10.149 --> 00:06:11.990 I think. It tells you about the demands of the 00:06:11.990 --> 00:06:14.649 early Internet versus the demands of being a 00:06:14.649 --> 00:06:16.870 touring stand -up comic. Right, juggling both. 00:06:17.009 --> 00:06:19.769 Exactly. It was clearly a passion project, but 00:06:19.769 --> 00:06:23.129 one requiring constant upkeep, nonstop production 00:06:23.129 --> 00:06:27.079 of fresh material. all while both creators were 00:06:27.079 --> 00:06:28.899 trying to build performing careers in what's 00:06:28.899 --> 00:06:31.560 already a grueling industry. Sure. It just shows 00:06:31.560 --> 00:06:34.079 how hard it is to sustain that kind of non -performance 00:06:34.079 --> 00:06:38.120 community work early on. But importantly, the 00:06:38.120 --> 00:06:41.680 themes that drove girlcomic .net, fighting sexism, 00:06:41.839 --> 00:06:44.740 highlighting unique female experiences, those 00:06:44.740 --> 00:06:46.839 are the exact same themes that would later make 00:06:46.839 --> 00:06:49.339 her books bestsellers. Ah, interesting connection. 00:06:49.720 --> 00:06:52.120 Yeah, the idea didn't really die. It just found 00:06:52.120 --> 00:06:54.759 a more, let's say, profitable and sustainable... 00:06:56.819 --> 00:06:59.519 That foundation of digital savvy, though, it 00:06:59.519 --> 00:07:02.600 certainly paid off down the line. By 2009, she 00:07:02.600 --> 00:07:04.860 was already getting formal recognition, named 00:07:04.860 --> 00:07:08.220 one of the top 12 rising stars in comedy by Entertainment 00:07:08.220 --> 00:07:10.480 Weekly. Yeah, and this momentum carried directly 00:07:10.480 --> 00:07:12.079 into the digital world where she'd already built 00:07:12.079 --> 00:07:14.839 some credibility. In May 2010, you had two major 00:07:14.839 --> 00:07:17.579 outlets, MSN and the Huffington Post, both naming 00:07:17.579 --> 00:07:20.259 her a top comedian to follow on Twitter. That 00:07:20.259 --> 00:07:22.639 recognition is really key, isn't it? It suggests 00:07:22.639 --> 00:07:25.459 her observational humor just translated perfectly 00:07:25.459 --> 00:07:28.600 to that, you know, 140 character limit of early 00:07:28.600 --> 00:07:30.360 Twitter. Absolutely. It wasn't just about jokes. 00:07:30.459 --> 00:07:32.800 It was about connecting. Right. It's a crucial 00:07:32.800 --> 00:07:35.439 insight, I think. Twitter demands immediacy, 00:07:35.579 --> 00:07:38.819 precision and a high volume of quality, short 00:07:38.819 --> 00:07:42.379 form stuff. That skill set, it's the same one 00:07:42.379 --> 00:07:44.720 you need for roundtable panel comedy. So she 00:07:44.720 --> 00:07:47.220 was connecting with her audience outside the 00:07:47.220 --> 00:07:50.050 traditional club structure and... At the same 00:07:50.050 --> 00:07:52.910 time, basically training for what would become 00:07:52.910 --> 00:07:55.750 her defining television role. OK, so that blend 00:07:55.750 --> 00:07:59.490 of digital smarts and consistent club work, it 00:07:59.490 --> 00:08:02.629 feeds directly into her most visible role. The 00:08:02.629 --> 00:08:05.230 regular roundtable panelist on East Chelsea lately, 00:08:05.449 --> 00:08:08.569 70 episodes, that's just consistent high level 00:08:08.569 --> 00:08:11.730 exposure over six years. unbelievable platform 00:08:11.730 --> 00:08:14.550 for honing that quick reactive wit oh definitely 00:08:14.550 --> 00:08:16.850 the panel format is such a unique high pressure 00:08:16.850 --> 00:08:19.269 machine you know you have to react incredibly 00:08:19.269 --> 00:08:21.629 quickly often to pop culture news you might not 00:08:21.629 --> 00:08:24.189 even care about that deeply right and land a 00:08:24.189 --> 00:08:26.069 punch line in a tiny fraction of the time you'd 00:08:26.069 --> 00:08:29.449 get on stage that experience it honed her technical 00:08:29.449 --> 00:08:33.330 writing skills immensely but here's where we 00:08:33.330 --> 00:08:34.909 see the volatility of the entertainment industry 00:08:34.909 --> 00:08:37.970 really hit hard Okay, walk us through that, that 00:08:37.970 --> 00:08:40.889 major pivot she made in 2010. Right. So June 00:08:40.889 --> 00:08:43.590 3rd, 2010, Kirkman announces she's leaving the 00:08:43.590 --> 00:08:46.590 whole Chelsea Lately Setup panelist, staff writer, 00:08:46.750 --> 00:08:50.350 everything. Wow. To take a major leap, joining 00:08:50.350 --> 00:08:52.950 the writing staff for NBC's romantic sitcom, 00:08:53.269 --> 00:08:56.450 Perfect Couples. NBC, primetime, big move. Huge 00:08:56.450 --> 00:08:58.590 move. From cable, where she was established, 00:08:58.690 --> 00:09:02.149 to broadcast primetime network TV. That was seen 00:09:02.149 --> 00:09:04.330 at the time as a significant step up, you know, 00:09:04.370 --> 00:09:06.429 prestige, potential stability. That sounds like 00:09:06.429 --> 00:09:08.909 a massive career risk, though, leaving guaranteed 00:09:08.909 --> 00:09:11.210 work on a hit show for an uncertain sitcom slot. 00:09:11.470 --> 00:09:13.750 It absolutely was a gamble. And the risk, well, 00:09:13.870 --> 00:09:16.429 it materialized almost immediately. Perfect Couples 00:09:16.429 --> 00:09:18.830 premiered in January 2011, highly anticipated. 00:09:19.169 --> 00:09:22.090 But network comedy slots are just brutal. By 00:09:22.090 --> 00:09:24.850 March 11, 2011, so less than three months after 00:09:24.850 --> 00:09:26.889 its premiere, NBC had already pulled it from 00:09:26.889 --> 00:09:29.379 the schedule. Wow, that fast. That fast. It was 00:09:29.379 --> 00:09:32.019 a swift, harsh lesson in the life of a television 00:09:32.019 --> 00:09:34.679 writer. A quick three month turnaround really 00:09:34.679 --> 00:09:37.159 shows the speed at which those high stakes network 00:09:37.159 --> 00:09:41.970 jobs can just vanish. But. The resilience is 00:09:41.970 --> 00:09:43.970 what stands out here. Exactly. And the silver 00:09:43.970 --> 00:09:45.850 lining is that the relationships she built back 00:09:45.850 --> 00:09:48.090 at Chelsea Lately were strong enough to support 00:09:48.090 --> 00:09:51.309 her immediate return. Oh, okay. By April 2011, 00:09:51.549 --> 00:09:54.149 she was back on the writing staff there, continuing 00:09:54.149 --> 00:09:56.470 to make occasional panel appearances throughout 00:09:56.470 --> 00:09:59.649 late 2010 and well after the NBC show collapsed. 00:09:59.929 --> 00:10:02.590 So she landed on her feet. She did. And she also 00:10:02.590 --> 00:10:05.429 appeared regularly on the spinoff after Lately, 00:10:05.610 --> 00:10:08.509 which gave that kind of fictionalized, self -aware 00:10:08.509 --> 00:10:11.389 view of the behind -the -scenes chaos. This whole 00:10:11.389 --> 00:10:13.309 episode, the pivot, the failure, the return, 00:10:13.409 --> 00:10:15.490 it's like a perfect little anecdote for understanding 00:10:15.490 --> 00:10:18.169 the adaptability and, frankly, the networking 00:10:18.169 --> 00:10:20.789 required for survival in comedy writing. Absolutely. 00:10:21.009 --> 00:10:23.789 Now, beyond the lately universe, her other major 00:10:23.789 --> 00:10:25.909 narrative highlight, the one that probably introduced 00:10:25.909 --> 00:10:28.850 her to an even wider audience, was drunk history. 00:10:29.049 --> 00:10:31.590 Yes. This is where that precise performance training 00:10:31.590 --> 00:10:35.120 meets, well, deliberate chaos. It's such a remarkable 00:10:35.120 --> 00:10:38.000 format, isn't it? It relies entirely on the narrator's 00:10:38.000 --> 00:10:40.340 charisma and their comedic structure somehow 00:10:40.340 --> 00:10:43.440 fighting through the inebriation. Right. She 00:10:43.440 --> 00:10:45.559 narrated for both the original Funny or Die sketch 00:10:45.559 --> 00:10:48.080 series and then the later Common Essential TV 00:10:48.080 --> 00:10:51.179 show. That sketch series episode specifically 00:10:51.179 --> 00:10:55.279 got huge acclaim. It won the jury prize for best 00:10:55.279 --> 00:10:57.879 short film at the 2010 Sundance Film Festival. 00:10:58.080 --> 00:11:01.580 Wow, Sundance. Okay. And the detail that gives 00:11:01.580 --> 00:11:07.350 the show its authentic... Edge, were the narrators 00:11:07.350 --> 00:11:10.009 actually drunk? Yes. The sources confirm this 00:11:10.009 --> 00:11:13.250 essential chaotic detail. Kirkman herself confirmed 00:11:13.250 --> 00:11:15.210 she was actually drunk for both episodes she 00:11:15.210 --> 00:11:16.970 narrated. Okay, so she wasn't just performing 00:11:16.970 --> 00:11:19.769 drunk. No. She was attempting to recall and narrate 00:11:19.769 --> 00:11:21.909 historical facts while maintaining the comedic 00:11:21.909 --> 00:11:24.730 beat all in an altered state. It's actually a 00:11:24.730 --> 00:11:27.090 real testament to the structural inherent comedy 00:11:27.090 --> 00:11:29.429 in her writing that it could survive that kind 00:11:29.429 --> 00:11:31.429 of delivery. That's incredible. And her broader 00:11:31.429 --> 00:11:33.330 visibility was pretty widespread, too, right? 00:11:33.389 --> 00:11:35.789 She wasn't just stuck on cable. Not at all. She 00:11:35.789 --> 00:11:38.409 had guest spots on virtually every major talk 00:11:38.409 --> 00:11:41.149 show. Conan, The View, The Late Show with Stephen 00:11:41.149 --> 00:11:43.909 Colbert. She also performed stand up on The Late 00:11:43.909 --> 00:11:45.830 Late Show with Craig Ferguson and popped up on 00:11:45.830 --> 00:11:48.009 comedy game shows like At Midnight. OK, so she 00:11:48.009 --> 00:11:50.429 was covering all the bases. Absolutely. This 00:11:50.429 --> 00:11:54.009 wide ranging TV exposure, it demonstrates a really 00:11:54.009 --> 00:11:56.929 comprehensive career strategy. She was hitting 00:11:56.929 --> 00:12:00.500 all the required comedic media. Voice work, like 00:12:00.500 --> 00:12:03.779 on home movies and super news. Right. Panel punditry 00:12:03.779 --> 00:12:06.860 on Lately, sketch comedy. Even on that short 00:12:06.860 --> 00:12:10.299 -lived 2007 show Acceptable Tyvee on VH1. Oh 00:12:10.299 --> 00:12:12.679 yeah, I vaguely remember that. And pure stand 00:12:12.679 --> 00:12:14.659 -up performance on the late night circuit. Yeah. 00:12:14.720 --> 00:12:17.019 She basically ensured that no matter which channel 00:12:17.019 --> 00:12:18.519 you were watching, you were probably going to 00:12:18.519 --> 00:12:20.460 run into her work somewhere. That consistent 00:12:20.460 --> 00:12:22.879 exposure must have boosted her recorded work. 00:12:23.100 --> 00:12:26.080 She started with self -help back in 2006. Yep. 00:12:26.120 --> 00:12:28.519 And her follow -up, Hail to the Freaks, which 00:12:28.519 --> 00:12:30.580 came out in... 2011, that was a real commercial 00:12:30.580 --> 00:12:33.860 success. It peaked at number 13 on the Billboard 00:12:33.860 --> 00:12:36.820 Top Comedy Albums chart. Number 13, that's solid. 00:12:37.019 --> 00:12:39.240 It is, and it's important to note the timing 00:12:39.240 --> 00:12:42.669 here. This recorded success validated her stand 00:12:42.669 --> 00:12:44.889 -up material right when her visibility on Chelsea 00:12:44.889 --> 00:12:47.970 Lately was at its absolute peak. Ah, synergy. 00:12:48.330 --> 00:12:51.649 Exactly. TV drove the album sales, proving the 00:12:51.649 --> 00:12:53.710 synergy of her different platforms. Then came 00:12:53.710 --> 00:12:56.110 the pivot to, well, the ultimate streaming platform, 00:12:56.389 --> 00:12:59.070 Netflix. Her album I'm Gonna Die Alone and I 00:12:59.070 --> 00:13:02.529 Feel Fine, released in 2016, that also served 00:13:02.529 --> 00:13:04.570 as her debut stand -up feature on Netflix, right? 00:13:04.590 --> 00:13:07.169 Correct. And this transition from the traditional 00:13:07.169 --> 00:13:09.850 audio album model to a streamed video special 00:13:09.850 --> 00:13:12.809 model it's like a textbook example of adapting 00:13:12.809 --> 00:13:15.370 to how media was changing for sure the netflix 00:13:15.370 --> 00:13:17.629 platform just expanded her reach dramatically 00:13:17.629 --> 00:13:20.710 it put her intimate highly personal stand -up 00:13:20.710 --> 00:13:23.049 in front of a global audience huge potential 00:13:23.049 --> 00:13:25.529 audience there massive and she quickly leveraged 00:13:25.529 --> 00:13:27.669 that success too with her second stand -up feature 00:13:27.669 --> 00:13:30.490 for netflix just keep living that premiered in 00:13:30.490 --> 00:13:33.090 january 2017 and was later released as an album 00:13:33.090 --> 00:13:36.149 in november 2018 the ability to just churn out 00:13:36.149 --> 00:13:38.769 quality deeply personal material consistently 00:13:38.769 --> 00:13:41.490 across all these formats that's a huge part of 00:13:41.490 --> 00:13:43.870 her career architecture okay so this brings us 00:13:43.870 --> 00:13:46.889 to her transition from performer writer to like 00:13:46.889 --> 00:13:50.169 a bona fide published author leveraging those 00:13:50.169 --> 00:13:53.220 stand -up themes for long -form narrative In 00:13:53.220 --> 00:13:55.980 2013, she hits literary success with her debut 00:13:55.980 --> 00:13:58.539 book, I Can Barely Take Care of Myself, Tales 00:13:58.539 --> 00:14:00.820 from a Happy Life Without Kids. Yes, and this 00:14:00.820 --> 00:14:02.779 is where that thematic consistency really pays 00:14:02.779 --> 00:14:05.299 off, big time. The book wasn't just popular, 00:14:05.440 --> 00:14:08.259 it like hit a cultural nerve, became a New York 00:14:08.259 --> 00:14:10.879 Times nonfiction bestseller. Wow, bestseller 00:14:10.879 --> 00:14:15.039 status. Huge. And the topic, Examining a Happy, 00:14:15.139 --> 00:14:17.830 Fulfilled Life Without Children. It was deeply 00:14:17.830 --> 00:14:21.149 personal, totally observational, but also controversial 00:14:21.149 --> 00:14:23.830 enough to generate massive discussion. Yeah, 00:14:23.850 --> 00:14:25.889 I remember that sparking conversations. It took 00:14:25.889 --> 00:14:28.049 the intimacy of her stand -up, which often touches 00:14:28.049 --> 00:14:30.750 on social norms and anxiety, and just expanded 00:14:30.750 --> 00:14:33.809 it into a full -length exploration. It instantly 00:14:33.809 --> 00:14:36.090 elevated her status beyond just the comedy scene. 00:14:36.250 --> 00:14:38.149 And she recognized that success and followed 00:14:38.149 --> 00:14:39.590 up pretty quickly, didn't she? Signed another 00:14:39.590 --> 00:14:42.590 book deal. Yep. Second book deal with Simon & 00:14:42.590 --> 00:14:45.480 Schuster. That second memoir, I Know What I'm 00:14:45.480 --> 00:14:48.740 Doing and Other Lies I Tell Myself. Dispatches 00:14:48.740 --> 00:14:50.919 from a Life Under Construction came out in April 00:14:50.919 --> 00:14:54.799 2016. So cementing her role as an author. Absolutely. 00:14:55.080 --> 00:14:57.860 And what's important here is the sheer versatility 00:14:57.860 --> 00:15:00.159 in her comedic writing. She wasn't just writing 00:15:00.159 --> 00:15:02.899 stand -up or memoirs. She also contributed several 00:15:02.899 --> 00:15:05.519 published essays to popular collections like 00:15:05.519 --> 00:15:08.960 Rejected, Tales of the Failed, Dumped and Cancelled, 00:15:08.960 --> 00:15:11.399 and Bad Sex. We did it so you don't have to. 00:15:11.519 --> 00:15:13.990 Okay. This just confirms her ability to write 00:15:13.990 --> 00:15:16.110 effectively across any narrative length, from 00:15:16.110 --> 00:15:19.169 a quick joke to a panel quip to a focused essay, 00:15:19.370 --> 00:15:21.970 all the way up to a full -length book. All right, 00:15:21.970 --> 00:15:23.909 let's track back to her original scripted writing 00:15:23.909 --> 00:15:26.409 for the screen. She has animation credits. Yeah, 00:15:26.470 --> 00:15:28.690 writing for kids, which is interesting. Two episodes 00:15:28.690 --> 00:15:30.610 of the Disney Channel series Phineas and Fer 00:15:30.610 --> 00:15:33.909 back in 2009, plus continued voiceover work on 00:15:33.909 --> 00:15:36.269 animated shows like home movies and Super News. 00:15:36.529 --> 00:15:38.250 Writing for Disney Channel seems like such a 00:15:38.250 --> 00:15:40.149 different muscle than her stand -up. Totally 00:15:40.149 --> 00:15:42.360 different. It requires a specific structured 00:15:42.360 --> 00:15:45.279 humor that contrasts sharply with her usual dark 00:15:45.279 --> 00:15:49.759 observational style. But now, now we see the 00:15:49.759 --> 00:15:52.620 pivot to creator trying to build her own universe 00:15:52.620 --> 00:15:55.100 based directly on those successful memoir themes. 00:15:55.460 --> 00:15:58.419 Okay, tell us about that. In November 2013, FX 00:15:58.419 --> 00:16:00.419 gave her a script deal for a show just called 00:16:00.419 --> 00:16:03.960 Jen. Jen? Yeah. Simple enough. What was the concept? 00:16:04.059 --> 00:16:05.519 It sounds like it might be a direct translation 00:16:05.519 --> 00:16:07.100 of her book. It was almost a perfect mirror, 00:16:07.200 --> 00:16:10.840 yeah. Set in Boston, her hometown, and focused 00:16:10.840 --> 00:16:13.399 on a recently divorced woman in her mid -30s. 00:16:13.419 --> 00:16:15.759 Okay, hitting all her key themes. Exactly. And 00:16:15.759 --> 00:16:18.460 the backing was significant. Chelsea Handler, 00:16:18.600 --> 00:16:21.279 Tom Brunel, Brad Wallach, all executive producing. 00:16:21.620 --> 00:16:24.120 The concept was clearly attempting to capture 00:16:24.120 --> 00:16:26.559 that zeitgeist of her best -selling memoir and 00:16:26.559 --> 00:16:29.379 transition it into a scripted, running sitcom. 00:16:29.700 --> 00:16:31.740 Which is, you know, the ultimate goal for many 00:16:31.740 --> 00:16:34.120 successful comics. Right, the sitcom deal. And 00:16:34.120 --> 00:16:36.240 even after that project didn't quite move forward, 00:16:36.279 --> 00:16:38.450 she tried again a few times. years later secured 00:16:38.450 --> 00:16:41.250 a development deal with abc yep kept pushing 00:16:41.250 --> 00:16:44.309 in 2017 a deal with abc for a show called the 00:16:44.309 --> 00:16:48.789 mighty quinn the mighty quinn and the theme still 00:16:48.789 --> 00:16:51.470 in that same vein exactly the same thematic vein 00:16:51.470 --> 00:16:53.909 proving the consistency of her personal brand 00:16:53.909 --> 00:16:57.009 the mighty quinn centered on a 39 year old character 00:16:57.009 --> 00:16:59.629 named quinn who decides to take a full year off 00:16:59.629 --> 00:17:01.629 from dating after being dumped on christmas day 00:17:01.629 --> 00:17:05.619 ouch Christmas Day. Rough, right. But both Jen 00:17:05.619 --> 00:17:07.779 and The Mighty Quinn, they're really case studies 00:17:07.779 --> 00:17:11.099 in how a comic tries to monetize and, well, fictionalize 00:17:11.099 --> 00:17:13.000 the observational material that made them famous. 00:17:13.380 --> 00:17:16.579 And also how challenging it is to get that specific 00:17:16.579 --> 00:17:20.180 kind of niche observational comedy approved for 00:17:20.180 --> 00:17:22.539 a network pilot. Yeah, that jump seems tough. 00:17:22.700 --> 00:17:25.960 But maybe the most surprising and arguably prestigious 00:17:25.960 --> 00:17:28.400 role, the one that truly shows the industry's 00:17:28.400 --> 00:17:31.000 respect for her technical comedic skill, was 00:17:31.000 --> 00:17:33.180 her work on The Marvelous Mrs. Maisel. Oh, absolutely. 00:17:33.400 --> 00:17:35.160 This role is arguably the highest validation 00:17:35.160 --> 00:17:37.559 of her pure craft. She contributed to seasons 00:17:37.559 --> 00:17:40.940 one and two in 2017 and 2018 as a writer, consultant, 00:17:41.039 --> 00:17:43.160 and producer. Okay, so multiple hats there. What 00:17:43.160 --> 00:17:45.559 was her specific responsibility? It wasn't just 00:17:45.559 --> 00:17:48.420 general advice. It was specialized, highly technical 00:17:48.420 --> 00:17:51.559 work, providing many of the actual jokes for 00:17:51.559 --> 00:17:53.839 the main character, Midge Maisel's, stand -up 00:17:53.839 --> 00:17:56.559 routines. Wow. So she was applying her deep understanding 00:17:56.559 --> 00:18:00.920 of modern observational comedy to write in -character 00:18:01.589 --> 00:18:05.670 period appropriate jokes for a fictional 1950s 00:18:05.670 --> 00:18:07.849 comic. That feels like a huge technical leap. 00:18:08.140 --> 00:18:10.000 It is. It's like the ultimate test of comedic 00:18:10.000 --> 00:18:12.000 architecture, isn't it? Yeah. You have to essentially 00:18:12.000 --> 00:18:14.880 remove your modern sensibility, your personal 00:18:14.880 --> 00:18:17.079 voice, the very things that made her a bestseller, 00:18:17.160 --> 00:18:19.720 and adapt to the joke structure, the societal 00:18:19.720 --> 00:18:22.539 constraints, the cadence of the late 1950s and 00:18:22.539 --> 00:18:25.000 early 1960s. Incredible. And the context just 00:18:25.000 --> 00:18:27.819 deepens this. The series, created by Amy Sherman 00:18:27.819 --> 00:18:30.240 Palladino, is loosely based on the early career 00:18:30.240 --> 00:18:33.180 of Joan Rivers. Right. A comedian Kirkman specifically 00:18:33.180 --> 00:18:36.640 cites as a primary influence. Wow, that is genuinely 00:18:36.640 --> 00:18:38.759 full circle. Writing for a character who kind 00:18:38.759 --> 00:18:40.759 of embodies the spirit of one of her own heroes. 00:18:40.900 --> 00:18:44.079 Exactly. And it just confirms her value as a 00:18:44.079 --> 00:18:46.680 pure joke mechanic. You know, writing jokes that 00:18:46.680 --> 00:18:48.700 work for Midge Maisel requires an understanding 00:18:48.700 --> 00:18:51.579 of how funny works, structurally, independent 00:18:51.579 --> 00:18:54.400 of personal delivery. She actually returned to 00:18:54.400 --> 00:18:56.799 that specific stand -up consulting role again 00:18:56.799 --> 00:19:00.019 in 2021, proving that specialized skill set remains 00:19:00.019 --> 00:19:02.880 highly sought after in prestige TV. Okay, so 00:19:02.880 --> 00:19:05.220 if we look at the whole picture. the totality 00:19:05.220 --> 00:19:07.900 of his career, the podcasting universe seems 00:19:07.900 --> 00:19:10.839 like the place where she maintains the most consistent, 00:19:11.039 --> 00:19:13.539 maybe intimate connection with her audience, 00:19:13.640 --> 00:19:16.359 like a weekly audio diary almost. Yeah, I think 00:19:16.359 --> 00:19:17.980 that's fair. It's sort of a foundational pillar 00:19:17.980 --> 00:19:21.299 that allows her to completely bypass the network 00:19:21.299 --> 00:19:23.980 filtering process, right? Her current weekly 00:19:23.980 --> 00:19:27.259 podcast is called No Fun, but its name has evolved 00:19:27.259 --> 00:19:30.599 over time. It was previously... I seem fun. And 00:19:30.599 --> 00:19:34.099 before that, having funlessness. The title shifts 00:19:34.099 --> 00:19:36.900 themselves kind of reflect that self -deprecating, 00:19:36.900 --> 00:19:39.579 often anxious tone of her observational humor. 00:19:39.779 --> 00:19:41.380 And she was a pretty vital part of that whole 00:19:41.380 --> 00:19:44.200 early all comedy podcast movement, too, wasn't 00:19:44.200 --> 00:19:45.839 she? Oh, yeah, definitely. She was a regular 00:19:45.839 --> 00:19:48.059 guest on the Crap Feast podcast. Right. Love 00:19:48.059 --> 00:19:50.920 the Crap Feast. And notably, a real fixture on 00:19:50.920 --> 00:19:53.779 the monthly Pod F Tompkast with Paul F. Tompkins. 00:19:53.839 --> 00:19:56.940 VFT. Yeah. That association with Tompkins is 00:19:56.940 --> 00:19:58.539 significant because that's where she got the. 00:19:58.599 --> 00:20:01.319 nickname, Sophie. Ah, the Boston roots again. 00:20:01.400 --> 00:20:03.420 Exactly. A clear reference to her Massachusetts 00:20:03.420 --> 00:20:05.759 background, which she seems to carry as a badge 00:20:05.759 --> 00:20:08.640 of honor. These appearances really solidify her 00:20:08.640 --> 00:20:11.200 position within the comedy community. They provided 00:20:11.200 --> 00:20:14.519 this unscripted long form platform that allowed 00:20:14.519 --> 00:20:18.160 for much deeper explorations of personal themes 00:20:18.160 --> 00:20:20.799 than, you know, a quick panel segment ever could. 00:20:20.920 --> 00:20:24.390 And that intimacy. probably directly fuels the 00:20:24.390 --> 00:20:26.710 material she later formalizes in her books and 00:20:26.710 --> 00:20:28.750 specials. Absolutely. It's all connected. Now 00:20:28.750 --> 00:20:31.450 let's dig into the core comedic DNA a bit more. 00:20:31.589 --> 00:20:35.029 Who influenced this highly personal observational 00:20:35.029 --> 00:20:37.970 style that's often, you know, tinged with a bit 00:20:37.970 --> 00:20:40.349 of melancholy? The list is a fascinating mix. 00:20:40.529 --> 00:20:42.849 It really is. The cited influences range pretty 00:20:42.849 --> 00:20:45.789 widely. Joan Rivers, Howard Stern, Roseanne Barr, 00:20:46.009 --> 00:20:48.589 Dave Chappelle, Chris Rock, David Spade. Quite 00:20:48.589 --> 00:20:50.740 a spectrum there. Yeah. And what's critical is 00:20:50.740 --> 00:20:53.759 the blend. You've got the high energy, almost 00:20:53.759 --> 00:20:57.400 shout driven comics like Stern and Rivers combined 00:20:57.400 --> 00:21:00.720 with the masterful, precise observationalists 00:21:00.720 --> 00:21:02.960 like Chappelle and Rock. This kind of explains 00:21:02.960 --> 00:21:05.779 her stage presence, which can be both intensely 00:21:05.779 --> 00:21:08.259 intimate and highly animated at the same time. 00:21:08.380 --> 00:21:10.420 But there's that anecdote about her childhood 00:21:10.420 --> 00:21:13.799 TV habits that really seems to crystallize how 00:21:13.799 --> 00:21:16.640 she found her unique voice, that permission to 00:21:16.640 --> 00:21:19.519 be intense on stage. Oh, absolutely. That story 00:21:19.519 --> 00:21:22.079 is key. As an eight -year -old, she'd sneak out 00:21:22.079 --> 00:21:24.400 to a friend's house just to watch uncensored 00:21:24.400 --> 00:21:26.839 Sam Kinison and George Carlin comedy specials 00:21:26.839 --> 00:21:30.839 on HBO. Wow, at eight. Okay. Yeah. And she recounted 00:21:30.839 --> 00:21:32.839 that really formative moment watching Kinison 00:21:32.839 --> 00:21:35.160 realizing, someone is yelling, I'm not in trouble, 00:21:35.259 --> 00:21:38.250 and it's funny. Huh. That's a great line. Isn't 00:21:38.250 --> 00:21:40.990 it? That idea transmuting inappropriate or intense 00:21:40.990 --> 00:21:44.029 emotional energy into safe, palatable humor that 00:21:44.029 --> 00:21:45.990 became like a cornerstone of her stage persona. 00:21:46.190 --> 00:21:48.809 It gave her license to be highly reactive, even 00:21:48.809 --> 00:21:51.230 anxious, in her stand -up delivery. And then 00:21:51.230 --> 00:21:54.049 there's the truly unexpected influence. Maybe 00:21:54.049 --> 00:21:57.099 the most revealing one. Morrissey, yes. She has 00:21:57.099 --> 00:21:59.339 cited the lead singer of the Smiths as perhaps 00:21:59.339 --> 00:22:02.299 her single greatest influence. Morrissey, really? 00:22:02.579 --> 00:22:05.619 She admits she's nothing like him personally, 00:22:05.799 --> 00:22:08.500 right? But she credits him specifically with 00:22:08.500 --> 00:22:11.240 providing the model for the ability to say morbid 00:22:11.240 --> 00:22:13.930 things with a sense of humor. Okay, I can sort 00:22:13.930 --> 00:22:16.049 of see that connection now. Yeah, this connection 00:22:16.049 --> 00:22:19.269 is paramount, I think, to understanding her observational 00:22:19.269 --> 00:22:22.069 style. It explains why her stand -up often includes 00:22:22.069 --> 00:22:25.410 that dark, self -deprecating edge, managing to 00:22:25.410 --> 00:22:27.470 be melancholic and hilarious simultaneously. 00:22:28.089 --> 00:22:30.470 She basically took the thematic structure of 00:22:30.470 --> 00:22:32.609 the lament, which is such a hallmark of the Smiths, 00:22:32.609 --> 00:22:34.970 and applied it to the personal anxiety of modern 00:22:34.970 --> 00:22:37.890 life. Fascinating link. Now, we've touched on 00:22:37.890 --> 00:22:40.490 how her personal life informs her material, but 00:22:40.490 --> 00:22:42.759 the marriage and subsequent divorce that provided 00:22:42.759 --> 00:22:46.619 a really clear monetizable case study, didn't 00:22:46.619 --> 00:22:49.059 it? Yeah, it really did. She married writer and 00:22:49.059 --> 00:22:52.240 director Neil Mahoney in August 2009 and the 00:22:52.240 --> 00:22:54.180 marriage dissolved fairly quickly. They divorced 00:22:54.180 --> 00:22:57.539 in 2011. The significant factor here is the public 00:22:57.539 --> 00:23:00.059 nature of the announcement. She revealed she 00:23:00.059 --> 00:23:02.380 was no longer married on the August 25, 2011 00:23:02.380 --> 00:23:04.680 episode of Chelsea Lately. On the show itself. 00:23:04.900 --> 00:23:07.500 On the show itself. Utilizing her platform to 00:23:07.500 --> 00:23:09.740 break the news directly to her audience. That 00:23:09.740 --> 00:23:13.380 choice to share such intimate news on what It's 00:23:13.380 --> 00:23:15.960 essentially a celebrity gossip show. That feels 00:23:15.960 --> 00:23:18.460 like a strategic move in itself. It immediately 00:23:18.460 --> 00:23:21.019 turned a private event into public professional 00:23:21.019 --> 00:23:23.700 material. It's the ultimate professionalization 00:23:23.700 --> 00:23:25.740 of vulnerability, isn't it? Yeah. The divorce 00:23:25.740 --> 00:23:27.680 immediately became the central subject explored 00:23:27.680 --> 00:23:29.980 directly in her subsequent memoir and stand -up 00:23:29.980 --> 00:23:32.779 specials. The sources absolutely confirmed that 00:23:32.779 --> 00:23:35.140 this highly personal material, the divorce, the 00:23:35.140 --> 00:23:37.119 trials of dating after, the choice not to have 00:23:37.119 --> 00:23:39.500 children, this became the most successful and 00:23:39.500 --> 00:23:42.160 critically acclaimed work she produced. She truly 00:23:42.160 --> 00:23:44.539 mastered the art of transmuting personal experience 00:23:44.539 --> 00:23:47.500 into marketable material across multiple platforms. 00:23:47.799 --> 00:23:50.740 She made her life the central engine of her entire 00:23:50.740 --> 00:23:53.799 output. So if we try to synthesize all these 00:23:53.799 --> 00:23:56.519 different moves, the club circuit grind, the 00:23:56.519 --> 00:23:59.359 failed pilots, the bestseller status, the technical 00:23:59.359 --> 00:24:02.839 consulting on Maisel, what is the key takeaway 00:24:02.839 --> 00:24:05.339 about the architecture of Jen Kirkman's career? 00:24:05.849 --> 00:24:08.569 Well, I think her trajectory demonstrates a really 00:24:08.569 --> 00:24:10.670 profound understanding of creative leverage. 00:24:10.990 --> 00:24:13.809 She didn't just find success in one lane, right? 00:24:13.910 --> 00:24:16.789 She ensured that every piece of her intellectual 00:24:16.789 --> 00:24:19.809 property, her comedic voice, her personal anecdotes, 00:24:19.809 --> 00:24:22.410 her political observations could be successfully 00:24:22.410 --> 00:24:25.650 packaged and repackaged as stand up, as a best 00:24:25.650 --> 00:24:29.089 selling book, as a pilot concept, even as outsourced 00:24:29.089 --> 00:24:31.750 consulting material. That's adaptability. It 00:24:31.750 --> 00:24:34.970 is. She's that rare comic who is equally adept 00:24:34.970 --> 00:24:37.549 at. writing the raw, immediate joke for a club 00:24:37.549 --> 00:24:39.569 audience and providing the structural backbone 00:24:39.569 --> 00:24:42.009 for a fictional TV show character decades removed 00:24:42.009 --> 00:24:44.690 from her own experience, she leveraged a strong, 00:24:44.750 --> 00:24:47.309 singular voice into genuine creative control 00:24:47.309 --> 00:24:50.410 over her output. That specific pivot you mentioned, 00:24:50.470 --> 00:24:52.990 from performing her own material, material rooted 00:24:52.990 --> 00:24:55.930 so specifically in her life, like the divorce 00:24:55.930 --> 00:24:58.730 or the child -free choice, to actively consulting 00:24:58.730 --> 00:25:01.609 and writing period -appropriate jokes for a fictional 00:25:01.609 --> 00:25:05.339 character like Midge Maisel, that... Feels like 00:25:05.339 --> 00:25:07.319 the definitive moment of technical mastery. I 00:25:07.319 --> 00:25:09.660 agree. And it raises a powerful question, I think, 00:25:09.660 --> 00:25:12.000 for you, the listener, to kind of mull over long 00:25:12.000 --> 00:25:14.839 after this deep dive is complete. Okay. If the 00:25:14.839 --> 00:25:16.759 source material shows that a writer's greatest 00:25:16.759 --> 00:25:19.319 strength is their observational depth and their 00:25:19.319 --> 00:25:22.640 deep personal connection to the material, what 00:25:22.640 --> 00:25:25.220 does it actually take? emotionally, technically, 00:25:25.440 --> 00:25:28.099 stylistically, to successfully translate that 00:25:28.099 --> 00:25:31.319 unique, deeply personal voice into outsource, 00:25:31.319 --> 00:25:34.160 high -quality, applicable jokes for someone else. 00:25:34.359 --> 00:25:36.839 It moves beyond just being funny yourself, you 00:25:36.839 --> 00:25:38.819 know? It requires understanding the structural 00:25:38.819 --> 00:25:41.160 mechanics of comedy so incredibly well that you 00:25:41.160 --> 00:25:43.180 can apply your knowledge to almost any context, 00:25:43.299 --> 00:25:45.859 any character, any era. The ultimate sign of 00:25:45.859 --> 00:25:48.559 a comedic architect, maybe? a blueprint that 00:25:48.559 --> 00:25:51.539 works on stage, on the page, and yeah, on prestige 00:25:51.539 --> 00:25:53.819 television. That's a wrap on our deep dive into 00:25:53.819 --> 00:25:57.839 Jen Kirkman's versatile and truly masterful career.