An Introduction

RIP late night comedy. Long live late night comedy.

I performed on late night TV for the first time in 2019. It was The Late Show with Stephen Colbert, a show that is actively slated for cancellation. Some see this show’s death as the result of a backdoor, shady deal by a vengeful president. Others see it as an inevitability of a changing media landscape. I personally suspect there to be a little of both columns. Interestingly, I had attended Colbert once before as an audience member in 2015.

The guest? Donald Trump.

I find his slaying of the show particularly cruel, because I know that they were so nice to him. Nobody will treat you better than the staff of a late night show you’re appearing on. Want some whiskey? Tyler the production assistant will be right back with that. Fancy salad? It’s yours. The key to 30 Rock? Just promise to give it back. How could you do that to Tyler, Donald?

My appearance on Colbert helped open the door to a full-time job at Full Frontal with Samantha Bee, another show helmed by a Daily Show alum. Trump famously loved us. Then, fresh out of lockdown—and a month before Full Frontal would be cancelled— I performed on The Tonight Show. I met the Stranger Things kid and I almost answered my dressing room door pantless when Jimmy knocked on it. A perfect day.

Unfortunately, late night is living on borrowed time. But don’t just take it from me. There are entire Emmy Award-winning shows about it. As someone whose career once revolved around the post-primetime slot, it’s a hard pill to swallow. When I began standup comedy in 2013, the path forward was through late night. Back then, young comedians believed that all of their problems could be fixed with a Conan set. It wasn’t true then, but it’s REALLY not true now.

Today, there’s less standup on late night than ever—and soon there will be less late night than ever. Watching the industry — and so many people’s livelihoods — implode has been devastating.

But a hack therapist once told me to “look on the bright side.” So I’ll try. Instead of crying at the burial of a beloved TV format, I prefer to evangelize my favorite thing about it. Jokes.

This will not be a newsletter bemoaning the slow bleed of an industry or whining about how my standup career isn’t where I thought it would be. There might be some of that, but the main focus here will be punchlines.

What I loved most about late night wasn’t the product placement, the half-hearted celebrity games, or even pretending our 11pm show hadn’t been taped at 4pm. It was always the jokes.

Every issue of this newsletter will feature a late night set that I love along with why I love it. Think of it as a sampler platter for comedians you might enjoy. I’ll spotlight sets from the year of our lord 2025 as well as earlier days of late night. I’ll even pick out my favorite joke and print it in text so you can butcher it in your head. While standup comedy is currently dominated by the 90 second TikTok, I believe the tight 5 minute set deserves its place in the sun. Or at least your spam inbox.

That’s The Joke

My first comedian is Josh Gondelman. His 2018 Late Night with Seth Meyers set contains a ton of laughs per minute (yes, I can be a stat dork about art) as well as a flawless A - is - like - B style joke.

“My dog’s name is Bizzy, but it wasn't always. When we adopted her, her name was Daisy—but we didn't like that, so we switched it to Bizzy. Very rude of us, because when we adopted our dog she was 8 years old. That's middle-aged for a dog. That's like meeting a 56-year-old human and going, "What's your name? Debra? Nah. I'm gonna go ahead and call you Barbara."

The way Josh says “nah” really sells the above joke for me. The set has a great mix of personality and punchlines, which can sometimes be at odds with one another. You know exactly who Josh is, but that’s not what he relies on for laughs. The Cleveland Cavaliers closer is great on its own, but having Josh’s non-jock personality in the mix makes the punchline hit even harder.

I also love a set that is unmistakably of a certain time. It’s not overtly focused on 2018, but the way Josh talks about women hyphenating is reminiscent of a lot of late-2010s culture war Twitter discourse. He also lists the Cavaliers’ starting lineup for the year. Kind of a giveaway.

If you want more Josh, follow him on Substack and Instagram. You can also watch his new hour special here: