The Secret Formula for Writing Letterman Jokes

Ben Schwartz as a guest on “Late Show With David Letterman” on January 28, 2015. Late Show with David Letterman/YouTube

After 33 years and 6,028 episodes, Wednesday night marks the final live airing of Late Show With David Letterman, the longest-running late-night talk show in history. To send it off, we buttonholed Ben Schwartz, a former Late Show freelance writer turned TV star and screenwriter. The Chia Pet-maned Schwartz began his career more than a decade ago as an Letterman page and has evolved into what Playboy now calls "more than just a guy known for his hair." You might recognize him as horseshit-spinning management consultant Clyde Oberholt on Showtime's House of Lies, or Aziz Ansari's wretched pickup-line-spinning best bro, Jean-Ralphio Saperstein, on NBC's late, lamented Parks and Recreation.

Once upon a time, he used to clear a path for Letterman as the host walked from the Late Show stage to an Ed Sullivan theatre bathroom. While working as a page, Schwartz tried to kick-start his comedy writing career by scrolling through Yahoo News and picking out the weirdest stories. He'd free-associate 15 to 20 jokes every morning and fax them to Letterman's office. Of the thousands of jokes he submitted, Letterman cracked 21 of them on the air. Schwartz later posted the discarded ones on a website he created, called He filmed comics like Nick Kroll and Seth Green reading the rejects, put the videos on YouTube and built an Internet following. As Jean-Ralphio would say, "When life gives you lemons, steal your grandma's jewelry and go clubbin'."

Today, Schwartz credits his work ethic—he has written for Robot Chicken and CollegeHumor Originals and is at work on an untitled comedy that will reportedly star Seth Rogen and be directed by Adam McKay—to his Letterman freelancing.

What are your earliest memories of Dave?

I grew up watching the show almost every night. As a kid, I had a lot of trouble going to sleep. My mom would fall asleep halfway through the monologue, and my dad and I would watch three-fourths of the show. Right around when the musical guest would come on, my dad would fall asleep, and then I would go to my room. It was such a part of my family structure. There's a point in your life when you have to decide: Are you a Leno Guy or a Letterman Guy? Everyone in my family has always been a Letterman Guy.

How did you start writing for Letterman?

I was just a freelance writer and got paid per joke. I wouldn't know if my jokes were accepted until I watched the show live as an usher, since I was also working as a page. There's this thing that every time Dave does his monologue he points to Paul Shaffer. It means there's no more monologue. So a few times, after he pointed to Paul and I realized none of my jokes made it, you can hear me audibly yell, "Oh, c'mon!" If he did tell any of my jokes, I'd get paid, like, $75, and because I had to buy a landline and a fax machine to fax in the jokes, all the money would go right back to the cost of the faxes. So I never made any money.

How many jokes did you get on the show?

In the two or three years I submitted, I got about 21 jokes on the show. Which is an incredibly low percentage, considering I wrote and sent them 15 jokes per day. But I wouldn't put it on my résumé until I got three jokes on the show, because then I felt like I was a legitimate freelance writer for Letterman.

What makes a Letterman joke different from all other jokes?

When I was freelance writing for Weekend Update on Saturday Night Live, the setups could be longer and the punch was quicker. But when you write for Letterman, it's one sentence to set it up and one sentence to punch it down. While I was submitting jokes, Steve Young, the head monologue writer, would give me notes. Usually, "You're taking too long to set it up." And then once you watch Letterman, you watch what he makes fun of—he loved making fun of Paris Hilton, George W. Bush and squirrels in New York City eating nuts. Any time there was nothing going on in the news, I'd write five jokes about squirrels and nuts. He'd be like, "It's so hot outside that a squirrel had to air-condition his nuts." He loves stuff like that.

How did the Letterman team react to your jokes?

I only knew when they accepted the jokes, and that was when I saw them on the show. If something big happens in the world, or something about a celebrity, like "Paris Hilton got rear-ended," then every writer will submit a similar sexual innuendo joke and it's unlikely yours will get chosen. So I started submitting really weird things, and every time I submitted, the last joke in my pile was always a joke that would never get on air—a really fucked-up joke. That's the kind of stuff we put on, the stuff that would never get on.

Did you ever get feedback from Dave?

I never really got feedback from Dave, but one time Steve Young told me he put one of my jokes on a list for Dave and Dave circled it. And I was just over the moon.

Did it help your career?

Writing jokes is a unique skill. I don't know if I could do it now; you have to build that muscle in your brain. It really trained me for writing for Robot Chicken and the screenplays I write now.

When did you first meet Letterman?

There are different positions when you're a page, like showing people where the bathroom is, taking the tickets and blocking off the area where the bathroom is when Dave goes up to the stage. I used to be so nervous each time he walked by me. The first time I shook his hand was when I went on his show this January. It took me a decade to get to that chair on his show. It was a really meaningful thing for me to go from page to guest on the show; my whole family was in the audience.

How different was it from the way you imagined?

When I was a page, I became close with all the stagehands and crew. I used to go onstage after the shows and kind of nonchalantly get in the chair and do my own monologues.

Were the coffee cups like the ones in your dreams?

Yes. I collect coffee cups from all the talk shows I'm on. I have a whole bookcase full of them.

Did you take anything else?

I took the cue card from the day I was on.

What are your best jokes that were rejected by Letterman?

"A small town in Brazil has declared May 9 as Orgasm Day. It's a holiday where women have to celebrate privately at night after the men have fallen asleep."

"It was reported that Mary-Kate Olsen will be moving out of the New York apartment that she shares with her sister Ashley. When Mary-Kate is packed, Ashley will fold her sister into a paper airplane and throw her back West."

"It was reported that baby Jessica, the girl who was rescued from a well 18 years ago, got married to a wooden bucket."

How about your best quips that he actually told?

"In Athens, a taxi driver returns an Olympic silver medal left in his cab. Unfortunately, the world will only remember the driver who came in seconds earlier and brought in the gold."

"A study shows that having a TV in your bedroom enhances your sex life. The same study shows that having a TV in your bathtub can kill you."

"Governor Arnold Schwarzenegger received 15 stitches in his lip from a motorcycle accident. I hope the stitches don't make it hard to understand what he's saying."

"A 20-year-old student set a new world record after solving a Rubik's Cube in 11.3 seconds. And ladies, he's siiiingle."

Correction: A previous version of this article stated that Ben Schwartz was an NBC Page at 30 Rock instead of a Letterman page at the Ed Sullivan theatre.