Whitmer Thomas is Still Cool

So True with Caleb Hearon

Caleb Hearon hosts Whitmer Thomas for a candid and often hilarious exploration of aging, identity, and the comedy industry. The pair navigat

Key takeaways

• Whitmer Thomas discusses his midlife crisis, specifically the tension between wanting to be perceived as cool and the reality of aging as a skateboarder.
• The hosts reflect on the grim reality of the comedy circuit, noting that many comedians' lives are marked by frequent memorial posts on social media.

Main topics

• Midlife crisis and aging
• Comedy industry culture

Notable quotes

Comics commit to the bit.

Conclusion

A deeply personal look at how artists reconcile their past identities

Transcript preview

Speaker 1 (0:02) Or if I feel sad or... upset I don't say anything about it and somebody be like are you okay and I'll be like what would Jack Nicholson have to say about that even though like I'm in that moment I'm like devastated right Speaker 2 (0:23) How you doing? I'm doing okay. Speaker 1 (0:24) Yeah? Yeah, I took a NyQuil and smoked a weed CBD thing to go to sleep last night, and so I do feel kind of like fucked up. Speaker 2 (0:35) I thought you were going to say before this, just to level out. Right before I walked in here, I took some NyQuil and smoked a CBD thing. Speaker 1 (0:40) I used to do it every time I got into an airplane, and then I was like, why do I feel depressed and awful all the time? This is like 18 to 21. Yeah. Speaker 2 (0:49) I didn't get into weed at all until I was like 27. And then maybe like a year into that, I started trying to do the edible on a plane thing. It happened to maybe three flights. And that first time that I was highway, I didn't like entrapped in the air. I said, we won't be doing this Speaker 1 (1:04) anymore. Speaker 2 (1:05) Yeah. Cause you can't do anything. You're just fucking sitting there like tweaking. And it's like, I don't Speaker 1 (1:09) want this. You're stuck and paranoid. Yeah. I was just doing the NyQuil on the plane back then. And I didn't smoke weed. I smoked weed the first time when I was maybe. Speaker 1 (1:19) 25 and it wasn't smoked it was like tincture oil whatever that shit is have you ever seen that yeah and I was uh it was on my birthday and a girl that I had a crush on would like squeeze it onto my tongue and I didn't feel anything after one minute and I was like I don't think it's working and then she did it again and I was high for three days three days whatever happened and that's Speaker 2 (1:42) Nancy Pelosi yeah that girl That girl was Nancy Pelosi. Best sex of my life. Yeah. Only. That's. Are you serious? That's really beautiful. Speaker 1 (1:53) You and Nancy only doing... Yeah, she said it's the only way she gets off. Speaker 2 (2:00) The I- I really Speaker 1 (2:02) love that. I really love that. She does the kneel afterwards. Speaker 2 (2:05) Yeah. Her little famous kneel. But she puts on the like cultural garb that she's not supposed to be wearing. But Speaker 1 (2:11) it's all different. What people don't know is it's all different kinds of cultural garb that she's not supposed to wear. Like she has a head, Indian headdress, Native American headdress. Yeah. She's got all the stuff. She'll put a dot right here. She'll do it all. Yeah. That's Speaker 2 (2:23) why she's a fucking freak. It's fun. She's so fun. Speaker 1 (2:26) God, I love that girl. I haven't hooked up with her in years. What? Speaker 2 (2:30) I know. It sucks. She just got so busy with work and everything. Yeah. And plus, just as you grow older, people grow apart. They Speaker 1 (2:36) do grow apart. Speaker 2 (2:37) Do you know what I mean? Like, it just sucks. Like, she and I, we used to have so much in common, but then it's like she's in Congress, I'm a comedian. It just, yeah, it sucks. Speaker 1 (2:43) Yeah. I mean, yeah. Last time I saw her was at the Waxahachie show, and she likes their old stuff, so she was kind of bummed. She's like a big P.S. Eliot fan. In the other only place, she was only playing like Tiger's Blood and stuff. Yeah. Speaker 2 (2:58) Yeah, I texted Nancy like two weeks ago because they announced. uh, they're not going to do Bonnaroo next year. And I knew she, I was like, she'll be in the dumps cause she fucking loves Bonnaroo. Speaker 1 (3:11) And Speaker 2 (3:11) so I text her and I was like, Hey, I heard about Bonnaroo. Like, I hope you're okay. She didn't text back, which is fine. But yeah, it just sucks. Cause we used to go to Bonnaroo like every year, man. And do. Speaker 1 (3:22) What do you think about how I just conked out on the improv towards the end there and couldn't think of anything? It was Speaker 2 (3:27) completely beautiful. And the good thing about that bit is it was dead seven seconds into it, and we decided to go ahead and keep her running. Speaker 1 (3:34) That's what it was like whenever I did improv. I tried for like a year, and I would just stand on the back line, and I would look at all the other improvisers and be like, they probably got something better than me. And then I'd just keep standing back there. Y'all Speaker 2 (3:46) got it. Y'all got it. Speaker 1 (3:47) And then I'd see an opening for me to tell a long story. Yeah. Well, here's where I jump in. Speaker 2 (3:55) I love that. I was, uh, I don't, what was I like as an improviser, Chance? You Speaker 1 (4:00) were very Speaker 2 (4:00) smart and very Speaker 1 (4:02) tactful, but also would like randomly get extremely physical. Speaker 2 (4:06) Yeah, that's true. I Speaker 1 (4:08) would start throwing people. Yeah. Well, that's Speaker 2 (4:10) because Speaker 1 (4:10) a window one time. Speaker 2 (4:12) Yeah. That was mostly when I'm with straight guys doing improv. I know what you guys like. You guys like to be thrown around a little bit. You like it to be like that. And so I would do that when I was with the girls. Of course I would like tone it down, but. We had an improv team for a while, Chance and I, and two of our buddies from college. And it was, they're all straight guys and me. So I would just, if I got bored with some dialogue they were doing, I would just initiate a fight scene. And that was beautiful. And Gabby Boyd joined that team eventually. So then Gabby was in there. And then Gabby and I would do like, we would do like grounded emotional scenes together. And then the boys would like sweep it and be like, Speaker 1 (4:48) or Speaker 2 (4:49) whatever the fuck. And Gabby and I would sit on the sidelines and be like, God. I wish there was more girls and gay guys here. And then eventually there Speaker 1 (4:58) was, right? Speaker 2 (4:59) Then eventually there were more girls Speaker 1 (5:00) and gay guys. Yeah, Speaker 2 (5:01) in improvisation. We recorded with Asher Perlman yesterday, and we started talking about improv, and he was like, everyone just turned the episode off. Speaker 1 (5:08) And I was like, yeah. I met Asher in Chicago in 2015. I was doing stand-up up whatever that old comedy club was. Up, up, I think is what it was called. Above Second City. Speaker 2 (5:23) Oh, the Up. Yeah, yeah, yeah, the Up. Is it called the Up Room? The Up Comedy Club. Yeah. Speaker 1 (5:27) And then I did the story, the monologue at the end. Asher was so funny. Speaker 2 (5:33) Asher's a good kid. He's a good kid. He's got a bright future, a good head on his shoulders. But Speaker 1 (5:37) people did just turn the podcast off, right? Yeah, for sure. They're like, Speaker 2 (5:40) we don't care. Speaker 1 (5:41) Up Comedy Club. Speaker 2 (5:42) Oh, my gosh. Well, you're in New York right now. How's it been going? Speaker 1 (5:45) It's good. I always say when I'm here that I don't ever know where I am or how to get anywhere. Speaker 2 (5:51) Where am Speaker 1 (5:52) I? Like in New York, if this was LA, the studio would be like on the corner. I think HeadGum in LA is like the most conveniently located podcast place. It's Speaker 2 (6:03) like Speaker 1 (6:03) Sunset in Hyperion. Yeah, where everybody is. Whereas this is in some weird warehouse and you take an elevator that doesn't really work. There's boxes everywhere and it's kind of scary. I think I shot something here once. See, we like that. We think that Speaker 2 (6:19) grit is very charming. Speaker 1 (6:22) It is charming. We like that. It's cool, man. We Speaker 2 (6:24) think it's nice that our guests are scared and confused when they arrive. It throws them off kilter and allows us to get a more honest interview. Speaker 1 (6:29) Yeah. Yeah, I mean, everything is confusing here, so I just kind of accept the confusion. Did you ever live in New York? Not really. A lot of people think I did or think I started here just because all my friends are from here. Most of the comics that I started with don't do it anymore in L.A. It was like peak. Speaker 1 (6:48) 2012 nerd comedy kind of. Yeah, Speaker 2 (6:50) like the Meltdown Speaker 1 (6:51) and Speaker 2 (6:51) shit. Speaker 1 (6:52) Yeah, Meltdown was great, but it was like, yeah, everything looked like, every poster looked like Nintendo or, you Speaker 2 (6:59) know, Speaker 1 (6:59) that time period. Like that millennial, like, didn't age well era. Like cats with lasers coming out of their eyes. Oh, shit, yeah. And I think all those people killed themselves. Speaker 1 (7:13) Hey, we have to laugh, Speaker 2 (7:15) but it is 100 % true. Truly, most of being in comedy is just reading memorials. Truly. Just getting online Speaker 1 (7:22) and seeing someone being like, when we were in the back room of the Chuckle Fuckers hut in Speaker 2 (7:27) Indiana, I knew this guy was going to be somebody. Never really panned out, but God rest his soul. Speaker 1 (7:32) It's like every fucking day you get on Instagram, you're like, new memorial, new memorial. Well, the difference between comics and musicians I've noticed is... Musicians complain about wanting to kill themselves all the time and then comics will you'll have like the best night of your life with them and then they'll go home and kill themselves Speaker 1 (7:51) Musicians are all talk. Comics Speaker 2 (7:52) do it. Comics commit to the bit. Yeah. Yeah. God, it's sad, but it's so fucking true. You truly will not know a single thing was wrong, and then it'll just be like, oh, yeah, memorial posts. Yeah. Call from their mom. Fuck. Speaker 1 (8:06) Damn. Speaker 2 (8:07) Sorry. It's what it's like. What do you want me? I can talk seriously about it. It wouldn't change it. It's really so, I mean, yeah, I don't think I'll ever do it, but there was a real window. Speaker 1 (8:17) Oh, absolutely. There was a time when I'd be driving to a show going, another sold out show. There's a gun next to me. I'd put it in my mouth. Speaker 1 (8:29) Dreams coming true. Oh, that tree looks like it could hold a noose. Speaker 2 (8:35) It could hold Speaker 1 (8:35) my Speaker 2 (8:35) car at 90 miles an hour in a beautiful way. Well, that's not a great thing to hear just because before we started recording, you told me you're going through a midlife crisis. So now I'm worried about my friend Speaker 1 (8:44) Witt a little bit. I am, yeah. I'm just kind of at this period where I'm like playing out every possible scenario. Like where I go, oh man, I should get a Subaru. Outback. That's reliable. Then I go, well, what if I buy it right now? And then one year from now, I see a red convertible where the top comes down. And then I'm in a financial crisis because, you know what I mean? Playing all those stupid little things out. Also, like, I've become fully embarrassed of being a skateboarder. Really? Yeah. I'm, like, completely ashamed of myself. Speaker 2 (9:19) I can't tell you how cool and hot it is that you're a skateboarder. That's the consensus. I think everyone thinks people who ride skateboards are cool and hot. Really? Speaker 1 (9:27) Yeah, 100%. Speaker 2 (9:28) Even Speaker 1 (9:28) as Speaker 2 (9:28) they get old? Yeah, 100%. Do you see the head shaking back here? Everyone's fucking bricked up thinking about the idea of it. It's cool and hot. Speaker 1 (9:36) If you saw me in New York City skating around from show to spot to spot, Caroline's, The Cellar, you know how comics do? Yeah. Speaker 1 (9:45) The way Speaker 2 (9:46) you're always at Speaker 1 (9:46) Caroline's in Speaker 2 (9:47) the cellar. Yeah. Speaker 1 (9:49) With a skateboard under my arm. To me, I'm like, that's excruciating. That's embarrassing. Speaker 2 (9:55) Wait, I can't tell you how cool that would be. Speaker 1 (9:58) Okay. Speaker 2 (9:58) We would all like that. Speaker 1 (10:00) Okay. Speaker 2 (10:00) And I speak for the general public here. That is very cool. Would I worry about you? Of course, your bones are getting a little brittle. I mean, you got to be real careful on that thing. Oh, yeah. But I don't think it's uncool. I think it's deeply cool. Speaker 1 (10:12) Maybe I'm just feeling self-conscious because I just did my new comedy special. I talk about skateboarding. And somebody in the, like, I saw a letterbox. My dad won't stop sending. My whole family sends me letterbox reviews. And they don't understand that, like, how it works. And a lot of them are bad reviews. Yeah. Speaker 2 (10:32) Or Speaker 1 (10:32) not bad reviews. They'll say something like, I didn't really like it. But I think it's cool that he likes his friends. Or something like that. My dad will send it and be like, so nice that they think it's great that you like your friends. Yeah, yeah, yeah. You miss the bad part, though. Speaker 2 (10:50) Yeah, you miss Speaker 1 (10:50) the part where they panned my work that I love. Speaker 2 (10:52) And Speaker 1 (10:52) one of those reviews says he seems sort of immature and it's weird that he still skateboards. And that's all I focus on. It's mostly nice stuff on there, but that's all I think about. It's like, damn, I am getting old. You can see it. And I skateboard. And, yeah, my bones hurt. And I still am like, I'm doing this thing now where I try not to dress like the kids Speaker 2 (11:16) skating. Speaker 1 (11:17) Yeah. Because I feel like, no, I need to. Look a little bit more grown up I can't because all the kids now are wearing like von dutch hats and true religion jeans and ed Hardy shirts like that's become popular in the skate world And I'm just like I'm not doing that too old for that. Speaker 2 (11:33) Yeah. Speaker 1 (11:34) Yeah Well, Speaker 2 (11:35) it's funny the two first things that came up in your midlife crisis. We're both just like modes of transportation You're right. Do I get the Subaru? Do I get the convertible? Am I allowed to skateboard? It seems to be a lot of anxiety about getting around Speaker 1 (11:47) Well, it's that, and I think it's also about wanting to be wanted, like wanting people to be like, oh, that's a guy or whatever. And as you get older, it's like. Speaker 1 (11:57) I don't know, man. It's like, I don't fucking know. I don't know what I'm saying. You want to be wanted. Do you feel wanted? Speaker 2 (12:07) Because I perceive you as very wanted. Do Speaker 1 (12:09) you? Yeah. When you pop up on my phone or when you come around, I go, everyone's Speaker 2 (12:14) excited to see you. People love you. People love your work, think you're a great artist. This is the genuine perception that I hold of you, what I think of you. I think you're a great artist and somebody that I want around. And then also, that's generally all that's ever said about you is good, nice things. Do you feel that? It's nice. Speaker 1 (12:31) No, I don't feel that. It's because you're reading the fucking Letterboxd Speaker 2 (12:35) reviews. Speaker 1 (12:35) I'm not reading. I had to say, like, hey, I don't read reviews. I don't look at this stuff, so please stop sending. And now they make fun of me, and they keep sending them, and I go, a little bird told me. You don't like reading these things. Sensitive old Whitmer doesn't want to see Speaker 2 (12:51) these. Speaker 1 (12:51) Well, too bad. So I think, you know, I'm like. I don't know how I'm perceived. This is something I've been talking about in therapy where I'll explain everything I just said to you and my therapist will be like, you look like people really like you. And I go, oh yeah, I guess. I wouldn't have even been invited to do that thing if they didn't like me or whatever. But maybe it's just like feeling like kind of like a... You know every time I talk about this I look back on it and I go wait no they liked me for sure like I was such an idiot when I was a kid and couldn't figure out like if a girl liked me Speaker 2 (13:26) and then Speaker 1 (13:27) as an adult I was like man I always had a yeah I've like encountered these women and I'd be like man and fuck junior year I had such a crush on you and I just didn't know what to do and she the woman would be like yeah I remember I would sneak in through your window take my clothes off and get into your bed and you wouldn't touch me. Speaker 1 (13:46) Fuck, okay, yeah, I Speaker 2 (13:47) guess that would have been a sign in some Speaker 1 (13:50) way. Speaker 2 (13:51) Damn. It's funny the thing you were saying about your family sending you stuff. I was up late last night, really late. It was like 3 in the morning that I was writing this email. I've been putting off forever. I have this movie coming out that's about my dad passing, and it's extremely fictionalized. There's a lot of things that are not true to what happened or true to my feelings. For different reasons, like, it just made sense that the second act needed this conflict moment or, well, you know, it's fucking filmmaking. Speaker 1 (14:17) Yeah. Speaker 2 (14:18) But I've been putting off writing this email to my family, just, like, to all of them to say, like, hey, this is going to come out soon. People are going to have reviews of it. They're going to say things in the reviews that might not feel like what you experienced when dad died. Like, basically just, like, level setting and being like, I'm used to this because it's my job, but you guys are going to experience a level of this that, like, you might not be used to. And I finally wrote the email last night and sent it. And my aunt, who's very, very funny and one of my favorite people in the whole world, my aunt Ashley responded to the email first thing this morning. And she said a bunch of sweet stuff and helped me contextualize it for everybody. And then she was like, also, I hope it's not a big deal. I sold a bunch of pictures of you to TMZ. And I was like, it made me feel way better because I'm really anxious about... I think I didn't maybe do the best job when I put out my special and I talked a lot about my dad. Speaker 1 (15:13) I Speaker 2 (15:13) don't know that I did the best job of helping my family process the way that people were going to. Because they'll see stuff online and get excited and they'll be like, that's Caleb. And then they'll read the comments and it'll be like, I'm talking about, I'll say like, oh, my dad was a nightmare or something. I'm being half serious because he was a very complicated person, but also I'm being silly and loving in the way that my dad and I would rib each other. He would think that was funny. And then people in the comments are being like, Like you know God to have a dad like that would be fucking horrible the guy sounds like an abuser or something like shit like that and then my grandma's reading that shit and being like it just is like really not fair to them because they didn't choose this life and I did and so anyway I was the reviews thing is so interesting because I'm like I wonder how much of that stuff they see. When Speaker 1 (15:57) they go the reviews kind of go one way or the other where they'll say like you're exploring your traumatic relationship with your dad or something where they'll go um he's able to make light of the passing of his eccentric father or something and yeah i would prefer they see that kind of thing i i mean i'm dealing with the same thing like my first special delta it was all about my mom and and uh I really roasted the hell out of my family. And in order for me to kind of feel comfortable doing that, I involved them in it, and I would do little interviews with them. But even that, it's totally me paying homage to my mom and how inspiring and beautiful she was, but she was also a total problem. Speaker 1 (16:48) And I was like out in Alabama and I had some family thing. And this lady came up to me and she's like, hey, do you remember me? We met when you were, you know, a preteen. And I stayed with you and your mom, with my daughter, who's your age. And I think like I watched your special and I thought that it was awful to your mom. And that. you painted her to be like a real monster. Jesus. And I was like, Speaker 2 (17:16) the fuck? Speaker 1 (17:17) Like, nobody has ever said that to me. Yeah. And then she goes, I go, well, that's not how I see it. And she goes, by the way, I thought whenever I brought my daughter to stay with us at your house when you were a kid that you had a crush on her and you might ask her out, but you didn't. Speaker 2 (17:39) This is fucking insane. And I was like, Speaker 1 (17:41) I was in eighth grade. What are you talking about? Speaker 2 (17:43) And she goes. Speaker 1 (17:45) Are you gay? Speaker 2 (17:46) And I Speaker 1 (17:47) go, Speaker 2 (17:47) I'm coming around on her. I Speaker 1 (17:51) was like, no. And she goes, okay, well then it's weird you didn't ask my. I was like, what do you, what is this? It's almost like she was, she wanted to be mean to me because I didn't ask her daughter out when I was in eighth grade. Speaker 2 (18:05) Yeah. And the first part of it, the stuff about the mom, I'm like, obviously I'm not on her side, but her being like, if you didn't ask my daughter out, you're gay. Of course I'm coming around. I Speaker 1 (18:12) do. I'm ending up in a place where I think Speaker 2 (18:14) she might be a legend, but that's fucking psychotic. She's insane. But I do love like 20 years later being like 30 years later being