Around 35 minutes into his new special, Joe List pitches a brilliant loophole for how you can get a complex drink made just how you like at Starbucks.

The wily comedian’s suggestion is simple: glance at your phone, act frazzled and tell the barista the beverage you’re ordering is for your boss.

“I don’t have a boss but this way they can be annoyed by the person I made up,” he quips.

This clever idea doesn’t get the biggest laughs of List’s hour, which he’s dubbed “Small Ball.” In fact, far from it. However, the bit is a perfect encapsulation of the Boston native’s singular brand of neurotic comedy. He obsesses over minute details and finds the funny in oft-overlooked situations like the origin of Mountain Dew, Ben Affleck tipping a waitress at a poker table and proper stroller etiquette.

And, while putting out a punchline-heavy special and touring the country might be more than enough for most comics, List double dipped this past year and just completed his feature film directorial debut “Tom Dustin: Portrait of a Comedian.”

The self-reflexive documentary follows his funny yet flawed comic friend, the titular Tom Dustin, who settled in Key West, FL, but can’t help but wonder what would have happened had he taken a chance on New York. Rather than acting as a fly on the wall, List inserts himself in the narrative and avoids cliché by painting a nuanced warts-and-all picture of an entertainer and friend deserving of more recognition.

That’s not to mention, it’s also very funny.

So, like List, we wanted go deeper. Our team took a magnifying glass to the oft-overlooked parts of the accomplished comic’s oeuvre — his “Last Comic Standing” past, marriage to fellow comedian Sarah Tollemache, parenting a one-year-old, narrative film works — and found out more about the man.

Here’s our conversation with comedian, writer, director, actor, podcaster and sometimes difficult Starbucks customer Joe List.

Joe, we loved “Small Ball.” What makes the new hour so special to you?

Every time I finish a special, I can’t believe that I did it again. You know, you’re doing an hour on stage and you’re like ‘how am I going to write material again? I’m not going to have this much stuff.’

And then you kind of do it. So it feels like a miracle every time. I feel like this one is better than the last one based on audience reactions. Plus, it ‘s the first one I’ve done that wasn’t filmed in New York at The Village Underground and it’s the first time I’ve cut together two different nights in two different venues. So it’s a lot of firsts for me.

I think it’s very good. I could be wrong.

Is there a meaning behind the title “Small Ball”?

I was opening for Louis C.K. nine years ago and we did the L.A. Forum, which is a huge 16,000-seat venue. I didn’t really know him at the time. Then, we all got on a private jet and he was like ‘what a night, that was the best show.’ F—ing Joe List playing small ball at the L.A. Forum.’ I’m a big baseball guy, and I just liked the metaphor of drawing a walk and bunting a guy over because you see so many specials that have a crane shot and it’s in a stadium or an arena or the guy comes up to the stage and there’s sort of a big act out, which is fine for whoever’s doing it.

But for me, I’m in a club talking about my d—, and [‘Small Ball’] just felt like apt name. It’s just here ‘I am standing here. I’m not going to move around a lot, but I’m going to get the job done. It’s not going to be too flashy.’

You have a lot of material out in the ether. Four hourlong YouTube specials and half hours on Netflix and Comedy Central. Where would you tell fans to start that haven’t consumed all of your work?

You don’t have to see the other specials to get them but “I Hate Myself” just hit 10 million views. That was the first hour I did on YouTube and people really responded. Well, maybe that’s the first one. I would tell people to go there and just watch them in order, if you can, for fun.

But all of them I think are are strong and good. Obviously, I think they’re good, I put them out.

How would you describe your comedic voice at this point in your career?

I don’t know. I never think of comedy in that way or those terms.

Whatever I think is funny in that moment is what I do. But I’ve had many bits through the years about how people think I’m a smart guy or educated but I’m not. I barely graduated high school and I’m not a nerd. People really think of me as this nerdy guy.

The number one comment I get after shows is that audience members didn’t think I was tall. I’m very tall, 6’2 and 180 pounds like an athlete, but I’ve had crooked teeth and glasses most of my life and a bad jawline. People think that I’m into sci-fi and I’ve never read a ‘Harry Potter.’ I’m horrible at math, I’ve never seen Lord of the Rings, I don’t play chess, and I got laid a good amount. I have no formal education whatsoever. I went to zero college. The other thing is I like foreign films, but I also am obsessed with hockey. So, you know, I’m a complex guy.

Will you be doing new material on your upcoming tour?

I’m in this weird area where I have about 45 minutes of new material and 40 of it is pretty good but still getting there. There’s a lot of stuff that ends with me being like, ‘alright, that’s how that ends now.’

And it’s filthy. I just did an hour at the Wilbur Theater and afterwards, my mother was like ‘you’re vulgar now.’ There’s a lot of sex and marriage stuff. A lot of going to the doctor stuff. The other day I was in the bathroom stall and the guy next to me yelled ‘f— you’ to his bowel movement. So I’m doing a bit about that. I’m not maturing at all.

Why did you want to make a doc about your friend?

Tom (Dustin) is always so compelling and funny, and I just thought it would work well. I wanted people to see him and know who he was because I have there are so many great comedians that don’t live in New York or L.A. or just haven’t really made much of an attempt to be known but they’re great.

It always bothers me that comedy fans are like, ‘well, if he was any good, I would have heard of this guy’ and I’m like ‘well, you’ve never heard of 98% of the comedians’ and there’s a lot of great ones out there. And I thought our friendship would be compelling, too. Plus, he kills iguanas. He runs a club.

The movie became much more than I anticipated. I really thought it was going to be Tom drinking, smoking and telling stories. Then it ended up being more about mental health than our relationship and the meaning of success.

Will you be making more documentaries like this?

Patrick Holbert, who produced, edited and shot the movie with me, was saying this could be a series but a part of me feels like Tom would be hurt if we did another one.

I am trying to make a documentary now about SkankFest and Luis J. Gomez would be a big part of that. We’d make it abot his life and the festival.

You’ve also made a lot of great absurd and observational shorts. Do you have more narrative stuff in the works as well?

Raanan Hirschberg and I just had a meeting over Zoom. We’re trying to write a sex comedy and I’m acting in some shorts. I’m always trying to make something. It becomes a little more difficult with a baby and a podcast. Podcasts always get in the way. It’s nonsense.

You and your wife Sarah roasted each other on Comedy Central. Was that a cathartic experience or did it open old wounds?

To pull back the curtain on that roast, we wrote together. We worked on all the jokes together and with the aforementioned Tom Dustin. He wrote about 70% of the jokes. He’s got a good mean streak and is obviously a brilliant writer. So we wanted to go over all the jokes because you never want to be surprised in a roast. You don’t want to find out something about yourself at a roast.

We went over what we were cool with and both of us were pretty good about letting the other ‘have at it’ since there’s not a lot there for us to pick at. It’s not like my wife cheated on me or vice versa. It’s more ‘he’s got crooked teeth, she was a stripper.’ So it was fun and there were no hard feelings whatsoever.

People were like ‘you must not have gotten laid for a year, you guys must have almost broken up’ but it’s like ‘no, no, no.’ We each knew what the other was going to say.

Do you have any parenting advice for comedians that are planning on having children?

Make sure you have a good, supportive wife. Just know that it’ll be okay and you’ll sleep at some other point. For me, I think comedy helps me because I was such a drunk lunatic for all of my twenties.

My wife and I always laugh because everything feels easier now because we don’t drink. All the baby challenges are much less difficult than getting on a cross-country flight, two hours after you finish drinking. That’s what I would say. Get get sober, get a good life partner.

Any great ‘Last Comic Standing’ stories?

I did it in 2010 when Craig Robinson was hosting and Greg Giraldo, Natasha Leggero and Andy Kindler were on the show. I got edited out that year.

Anyway, there was a long dead spot when we were waiting to roll camera and Craig Robinson reminded us ‘everybody remember to see my movie ‘Hot Tub Time Machine’ and Greg Giraldo said ‘what’s it about?’ That was great.

Then, the second time I auditioned, I made it on. Norm MacDonald was the judge and was just so nice to me all the way through. He tweeted out, ‘there’s five great comedians and one of them is Joe List’ or something like that. I have it somewhere.

This interview has been lightly edited and condensed for clarity.

Want to see List live? He’ll be at New Jersey’s Stress Factory Comedy Club from Nov. 6-8.

A complete calendar of all the venues you can see List at — including dates and links to buy tickets — on his upcoming tour can be found below.

Typically at the end of stories we like to recommend artists similar to the subjects covered above. However, this time, we let Joe List take the reins.

Here are his favorite working comics that he thinks you ought to see live.

I love Maddie Weiner. She blows me away. I think she’s going to be huge. She’s like my favorite right now. Just works her a– off and is so young.

Daniel Simonsen is another one. He’s Norwegian and has such beautifully honest, dark stuff. Sam Morril, of course. My opener Luke Mones. It’s always weird when people who started after you become your favorite comedians.

And Colin Quinn, I always love to see.

Who else is on the road? Check out our umm list of all the biggest comedians on tour in 2025 to find the show for you.