The Funniest David Letterman Jokes and Moments for the Comedy Hall of Fame
Following a run of successful guest-host appearances for Johnny Carson on The Tonight Show, David Letterman had an auspicious start to helming a show of his own. The David Letterman Show was a morning talk show that showcased his acerbic wit and willingness to push boundaries — and NBC pushed it right off a cliff after four months.
But the experience teed Letterman up for what became the quintessential weirdo late-night comedy show from the mid-1980s to the early 1990s. Buoyed by a desire to completely deconstruct the late-night format, Late Night with David Letterman produced memorable bit after bit and cemented Letterman as a talk-show icon. His move to CBS and The Late Show with David Letterman dulled the edge significantly, but it still orders better than The Tonight Show with Jay Leno.
With all that in mind, we’d like to honor Letterman’s contributions to comedy with 15 of our favorite, Hall-of-Fame worthy Late Night and Late Show gags and moments.
Throwing Things Off High Places to See What HappensA remarkably stupid idea that turned out to be everything we never knew we wanted: Watching stuff fall to the ground and go splat! Letterman started off on Late Night by chucking disco balls, balloons full of guacamole and a napalm birthday cake from a five-story tower. Eventually, The Late Show switched to closing down the street outside of the Ed Sullivan Theater and having interns toss even crazier things out of a seventh floor window, like trying to crush a wax figure of Letterman with a safe or dropping a bowling ball into a bathtub full of chocolate pudding.
Messing with His Own Reruns
Whenever late-night hosts take a week off, the network typically just goes with reruns. Letterman, though, would go out of his way to make the reruns of his show insane — e.g., dubbing them in a foreign language, or providing a running commentary throughout.
Apologizing to Bill Hicks’ Mother
On October 1, 1993, Hicks performed at a taping for The Late Show, only for it to be decided that Hicks’ material was unsuitable for broadcast. It would’ve been Hicks’ 12th time on the show, and he knew it would almost definitely be his last, as he was undergoing chemotherapy for pancreatic cancer. After Hicks died four months later, Letterman carried the regret of that cancellation with him for years. In an attempt to make things right, on January 30, 2009, Letterman aired the forbidden set as well as invited Hicks’ mother, Mary, on the show for an interview.
Hosting a Show from Home Long Before Anyone Had To
Since the pandemic lockdowns, seeing a late-night host do their show from their house isn’t that new, but back in 1983, apropos of absolutely nothing, Letterman started his show remotely from home, under the guise that he couldn’t make it into the studio because he had to wait on the cable guy to show up. They even had Jerry Seinfeld awkwardly stall for time while Letterman was on his way back to the studio.
Stupid Pet (and Human) Tricks
In 1982, Letterman kicked off the Stupid Pet Tricks segment, and 18 months later, he expanded the idea to Stupid Human Tricks as well.
Working the Drive-Thru
These segments really demonstrated Letterman’s charisma — to be able to criticize would-be customers’ orders or to strike up ridiculous conversation via the drive-thru speakers and not get assaulted was a true wonder.
Hello Deli
After Letterman made the move to CBS and the Ed Sullivan Theater in 1993, he sent his camera crew out to visit some of the other businesses in the neighborhood. After the crew popped into the Hello Deli around the corner and met owner Rupert Jee, a friendship (and TV star) was born. Jee made 400 more appearances on the show, either by Letterman sending in the cameras to the deli or by asking Jee to abandon his post and come over to the studio.
Late Night Monkey Cam
Another self-explanatory idea that was too stupid not to work — they strapped a camera to a chimpanzee named Zippy and let it run around the studio.
Keeping His Cool During Some Incredibly Unexpected Interviews
You can’t spend 33 years hosting a late-night talk show without some crazy shit happening, but Letterman managed to keep it together through some truly wild moments. Like when Drew Barrymore flashed him for his birthday, the multiple times cartoonist Harvey Pekar relentlessly badgered him or Oliver Reed was about to beat the ever-living crap out of him. Letterman’s most infamous guest interaction, though, was probably when Crispin Glover capped off an already batshit insane interview by nearly kicking Letterman straight in the face.
Helping Generate Controversy, Too
Letterman wasn’t above playing along with the occasional stunt, though. Like when Joaquin Phoenix came on the show looking bombed out of his mind and said he was retiring from acting to become a rapper, only for us to find out later it was all a ruse for his fake documentary/performance piece I’m Still Here. Then there was the fake feud between Andy Kaufman and wrestler Jerry Lawler. They let Letterman in on the gag beforehand and told him to just play along with whatever happened. Lawler slapping Kaufman wasn’t part of the original plan, it was a spur-of-the-moment ad-lib, but it made the whole charade seem all the more real.
Devoting an Entire Episode to Warren Zevon
Zevon had been a guest on Letterman’s shows for years, even subbing in as bandleader on occasion. After Zevon announced that he had been diagnosed with terminal cancer, Letterman invited him on the show as the only guest for the entire hour. They discussed his lengthy career, his diagnosis, the nature of life and celebrated his music. It was a lovely tribute and a pre-eulogy of sorts.
Bringing His Mom on the Show
Letterman started having his mother, Dorothy Mengering, on the show back in 1986, and she quickly became a fan favorite. She was the only person on earth who knew how to perfectly shut down Letterman’s foolishness.
The Alka-Seltzer Suit
Letterman had many suit-gag segments over the years that were part comedy bit, part physics lesson. He once wore a suit covered in packets of Rice Krispies and submerged himself in a giant bowl of milk to see how loud the snaps, crackles and pops would be. He put on a suit covered in magnets and stuck himself to a giant refrigerator. He wore a fireproof suit covered in 500 marshmallows, and you can guess what happened from there. But the best suit had to be the one covered in 3,400 tablets of Alka-Seltzer, in which he then dunked himself in a 900-gallon water tank.
His head writer at the time, Steve O’Donnell, nearly died testing out the suit during rehearsal. The reaction from the tablets made the air above the water too saturated with carbon dioxide, and O’Donnell barely had enough oxygen around him to be able to say, “Get me out of here!” That’s why, when Letterman did it for the show, they supplied him with a scuba tank.
Trolling the Jay Leno/Conan O’Brien Situation
It’s hard to say who screwed over Letterman more when he was robbed of The Tonight Show hosting gig back in 1993 — NBC or Jay Leno. But 16 years later, when Leno handed over the reins to Conan O’Brien, only to take the show back from him seven months later, there was only one person everyone really wanted to hear chime in on the matter. Letterman didn’t disappoint.
The Top Ten List
Letterman’s Top Ten Lists were a nightly staple starting in 1985 on Late Night all the way through to his final Late Show in 2015, although NBC did briefly try to stop him from doing them after he moved to CBS, claiming the gag was their intellectual property. The lists would always be something nonsensical like “Bigfoot’s Top Ten Pet Peeves” (#1: Driver’s license photo makes him look like Gregg Allman), and Letterman would count down each item as the band’s drummer gave him a steady drumroll. On occasion, Letterman would bring out his celebrity friends to help, too, such as with his final Top Ten List here:
