Joe List's Letterman Debut & A 12-Week-Old Baby

What I learned interviewing the comic followed by hot takes from a new mom

Image courtesy of Greenwich Time

I’m going to be very honest with you. Because if we can’t have transparency with Substack friends, well, what is this world coming to? I still don’t have transparency into what the word “Substack” means, but that’s neither here nor there.

I think my 12-week-old son is trolling me. This week he slept from an unprecedented –though that word should definitely be discontinued for overuse after the unprecedented pandemic– 7pm to 7am and my husband and I were so darn pleased. Man, we thought the whole world had opened back up for us. The next day I got it in my head he was ready for a trip to the suburbs (the baby, not the husband, who for that will never be ready), and since then he has been screaming an unprecedented freaking loud to SO FREAKING LOUD WE MAY HAVE TO MOVE.

He’s not yet verbal, but the subtext was this:

“Guess what Mom, I sleep through the night now!!”

“Lol, you believed me?”

Which brings me to…I didn’t sleep much and therefore couldn’t think much this week, so this weekend’s post is a remix of an interview I did with one of my favorite comics early last year. Hope you like it.

Interview

In my ongoing trek to understand the ever-elusive “Big Break,” I chatted with comedian and fellow traveler in the pothole-filled road of anxiety, Joe List (Netflix, The Tonight Show, Letterman, Conan, Joe Rogan) about his Late Night debut back in 2014. We spoke just before the release of his latest special "This Year's Material," which has since racked up over 2 million views, about how he made it happen, and the best advice he received to calm green room jitters.

Catch him on "Tuesdays with Stories" his weekly podcast with Mark Normand, his 2020 special "I Hate Myself,” "Joe and Raanan Talk Movies" with Raanan Hershberg, the Comedy Cellar, and many other places that aren't McDonald's (you'll get it once you read).

The following interview was recorded in 2022 and has been edited for readability.

LC: The structure of the show is I ask everyone to walk me through a pivotal gig in their career that help them get to the next level. So I was wondering if for you that would be your first time on Letterman. You've done a ton of stuff.

Joe List: Thank you. Yeah. Letterman was definitely the most pivotal, it felt like, at least mentally.

LC: How did you book it and what led up to that? And were you nervous and how did you decide your set?

JL: Oh, great. There's a lot there. So I, I had been I've been doing standup for when I did Letterman. I'd been doing stand-up for a long time for, like 12 years. And I was drinking heavily through most of that 12 years. I had always wanted to be on Late Night because that felt like what a comedian does.

And I was always really, really bitter about not doing Late Night. And then I got sober in late December 2012. And, you know, you get sober, you start to reflect on your life and decisions. And I realized I had been very bitter about not doing Late Night television. And then I realized that I had never actually tried to do Late Night television.

LC: I had a similar experience where I was extremely mad that I wasn't getting the comedy jobs I wanted to. Like, I couldn't watch SNL. I hated everyone that was doing comedy. And then I got sober and was like, Oh, but I haven't been doing comedy...

JL: Yeah. It's just it really is like so obvious, but you kind of, like, open your eyes and you're like, Oh, I've literally never submitted a tape or put together a set or anything. I've never I don't even know how you get on a Late Night [show], but I had spent like ten years being upset because I really thought that they would just come and knock on my door and be like, "Okay, it's time for you to go on Letterman."

So anyways, I got sober and then I went to Gary Gulman, who is a friend of mine and one of my favorite comedians, and he was shooting Letterman. And so I went with him as his guest and hung out backstage. And then it was there that I was like, “I should really try to do this. Why couldn't I do this?”

And I was thinking about that the whole time. And then we met the booker there, and he said, "Hey, if you ever want to submit a tape, here's my card." And I went, "Great." And so then I put together a set like I went and recorded 5 minutes at the Comedy Cellar.

I think I sent them the tape and kind of started the process, and they would take like three weeks to write back and they would write "We like this joke. We don't [like this one]." And it was a lot of back and forth with making new tapes, which was very frustrating. And then at one point, they were like, "We saw you do this joke about McDonald's that we love.

We want you to do that. And I was like, "Can I talk about McDonald's? Aren't they a sponsor?" And they were like, "No, no, you can." And then I submitted that. And after like two months of working on that set, they were like, "It turns out you can't make fun of McDonald's." And so and it was one of those things we were like, "That's what I told you."

But so we went back and forth for a long time. And then Letterman announced he was retiring and that really threw like a wrench in everything because he had one year left. And so everybody all these comics wanted to come on. He wanted to get all his favorite guests on and basically, they we stopped hearing from them, the bookers, for like three months.

And my manager at the time was like, we have to just move on. They're just not responding. And I was so frustrated that I said, "No," I get - I've never, like, asserted myself in my whole life, but I was like, "Get them to write 'no,' I want a written ‘no’." Like, we've had back and forth for like six months.

And I was like, “Please make them write ‘Just kidding, he can't come on the show.’” Like, I don't want it to just be ghosted.

LC: Right.

JL: And I was like, “Please just go and get them to write something back,” and it sounds like a movie story, but the next thing they wrote back was a date [to be booked to perform on the show]. I feel like they were just like shamed. And then they sent me a date to do it, which was very thrilling. And I believe, I could be fact checked on this, [but] I think I'm the last comic to debut on The Late Show. Like Norm McDonald was the last comic to be on, but I think I was the last guy to do his first Late Night on Letterman.

LC: And so when you were actually there, who did you bring with you in the green room?

JL: I brought Gary Gulman. I had gone to his.

LC: It's a nice full circle experience.

JL: Yeah, that was great. And Nick Di Paolo, who had been like my comedy dad, I opened for him for years. I don't condone everything he says. Nick is so controversial; I have to make that note. But he is a great friend of mine and I love him. And then my wife came and then my parents were in the audience. So backstage was Gary Gulman, Nick Di Paolo, my wife, Sarah Tollamache, and my manager, Maureen Taran.

LC: And did you say you're set exactly the way you planned or were you like "I hate McDonald's!" ? Did you have any last minute verbal explosions?

JL: No, well I did a flub a lot, I've done five Late Night sets and four of them flubbed a line at some point just because you get so, like, jacked up. So I did something like that.

LC: Did they let you redo it?

No. I just kind of had to live with it and had this weird moment…I think there's a story about some guy. I think Sebastian Maniscalco, actually, which really makes me feel good whenever I do a Late Night[show]. He just froze, evidently, for like an extended period of time and just started the whole thing over. I think if you messed up bad enough, you could be like, "I got to do this over again."

JL: Essentially, it was exactly what I had submitted, but, I mean, it was terrifying.

LC: I bet. But I know you're you're open about having anxiety, which I have through the roof. And how do you rein that in for stand-up? Because even normal people that aren't sober and don't have anxiety and depression would be nervous doing that.

Get more of Joe’s answers and anxiety coping techniques by subscribing and/or watching our interview below.

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What I learned from Joe

• It’s very easy to resent doors closed to you that are not, in fact, closed. While it would be great to jump ahead ten steps and be on Letterman without ever doing an open mic, that’s just not how life works. Rather than throwing a shoe at the TV every time SNL airs because they haven’t called to beg you and your untapped talent to join them, try taking one baby step towards your goal. If it’s comedy, try writing one joke, or even an amusing tweet. Whatever it is to you. There’s no workaround to doing the work.

• “My advice is, you don’t need my advice.” This was said to him in reference to green room jitters but is, like avocado, good in a variety of situations.

• “The anxiety about the thing is almost always worse than the thing.” So in the spirit of the new Ben & Matt movie, “just do it”!

Meanwhile, in Babyland…

Photo by Jonathan Borba on Unsplash

As our son is now a whopping twelve weeks old, we are officially free of the Netherworld that is “the fourth trimester,” as it’s called by websites trying to sell me more maternity clothes. Looking back on the baby registry I put together when I was pregnant -which feels like 30 years ago- I definitely had no clue what I was doing and registered for a lot of impractical cute decor he could care less about.

So, now that I have a whole three months of experience as a parent, here’s a look at things that were helpful and not so helpful this week:

Helpful

Hatch Sound Machine - We use this almost constantly. Helps him sleep and radiates a breadth of neons like your own personal baby rave. ‘90s forever!

Alo Running Shorts - When my husband saw these and said “Oh, like, mom shorts,” I almost dropped them directly in the trash, but it turns out they are lined, have a zippered pocket for your keys, and come in fun colors moms need (start this Ali Wong video at 5:35 for context).

Succession - The season four return of King Lear for the Brunello Cucinelli set was a great antidote to infant-centric days and nights. I wrote a silly thing about it here, and have been loving Amy Odell’s fashion recaps of each episode on her impossibly chic Substack Back Row. (Hunter Harris writes a great Power Ranking of each episode too on her Substack, Hung Up , if you, like me, can’t get enough of those bickering billionaires rn)

Boon Cacti Bottle Cleaning Brushes - Not only do these have major Tennis-camp-in-Scottsdale-AZ vibes, they are just the right sizes to fit in all the nooks and crannies of all the bottle parts I have to clean every 30 seconds.

Substack Notes - A newer, nicer answer to Twitter debuted this week, and so far, I’m into it. Though I’m so scared from traditional social media trolls it does take me a second to realize every nice comment is not sarcasm. Let’s make like Beethoven (the man, not the dog) and write some notes!

Not So Helpful

Dr. Brown’s Bottle Warmer - We do use this 5x a day, but it’s probably not necessary. R.I.P. counter space.

Law & Order - I was a die-hard SVU-head for decades, but now I it just bums me out. Idk how much Benson and Stabler will-they-won’t-they be more than friends; keep it light and binge Party Down before it comes back instead.

Baby fingernails - He keeps scratching himself in his sleep. Not good.

Hot almost-summer days - Pro Tip: Babies friggin’ hate their strollers in the heat.

The New Yorker - Even though the reporting is both thorough and balanced, he just has no interest.

For your viewing pleasure, here is Joe’s aforementioned and very funny special: