In the final years of his late-night career, David Letterman has been more or less glued to his chair in the Ed Sullivan Theater. But Letterman earned that time off his feet with a storied history of remote segments, unscripted comedy bits filmed outside the studio. As he retires, it’s safe to say that no late-night host has taken their wit into the world quite as effectively as did Dave. He may have idolized Johnny Carson in the studio but, in public, he drew more influence from original Tonight Show host Steve Allen, who pioneered the man-on-the-street bits that Letterman made into his signature.
Starting on NBC’s Late Night program, which he created in 1982, and The Late Show on the CBS, which he has hosted since 1993, Letterman filmed remotes everywhere from the offices of handwriting analysts to Italian-American neighborhoods in New Jersey. He even took a camera crew with him on personal errands like collecting his CBS photo ID or getting his teeth cleaned. As he put it himself when introducing a tape of another trip to the dentist, “Regular viewers of this program know that there is no part of my private life that I haven’t shared openly and generously with the curious public.”
In the spirit of Late Night and The Late Show, here are the top ten times Dave has shared his public excursions with us.
Letterman spent a lot of time roaming the streets of New York City in the first few years of Late Night, wandering into random businesses and chatting with passersby. It was innovative comedy even when his quips didn’t land. But Dave struck comedy gold when an employee at a store called Just Bulbs sarcastically suggested he should go to a store called Just Shades if he wanted to buy lampshades because he did exactly that: He found a store called Just Shades and asked them what else they sold.
A few months before Letterman famously interrupted the The Today Show with a megaphone (see later in this list), he practiced using his bullhorn on New Yorkers standing near a hot dog cart on the street below 30 Rock. From the window of an NBC executive, Letterman tried to persuade someone—anyone—to buy him five hot dogs. He didn’t succeed in procuring the dogs but he did leave us with this unforgettable forerunner to his similar proclamation on the Today Show: “Attention people of New York: My name is Len Lucas. I am an NBC executive. I am not wearing pants.”
“Fun With a Car In L.A.” is a beautiful collage of early Letterman tendencies produced well into his Late Show tenure. It combines his love for crushing things, pulling pranks, driving around Los Angeles, and ordering fast food all into one five-minute remote. Letterman doesn’t need any pre-arranged scenarios or iconic landmarks to have fun in L.A., he just needs a convertible full of tacos, a bottle of chocolate syrup, and some unsuspecting bystanders. It’s a taste of 1985 Dave wrapped up in the production values of 1995 Dave.
One of his best remotes and also one of his first, this hard-hitting journalistic inquiry into Alan Alda’s favorite Chinese restaurants captures Letterman’s impish energy in the early years of Late Night. At the time, Alda was a huge star on M*A*S*H and Letterman exploited restaurant owner’s pride at having served him to ask weird, invasive questions about his ordering habits: “His rice: steamed or fried?.” Letterman loved to parody local television journalism—see his famous “Shame of the City” segments—but he never outdid this take on the genre.
Much like fast food, this remote has a long list of ingredients: Dave, a Pontiac convertible, several fast food restaurants, an interior decorator, and Hungarian socialite Zsa Zsa Gabor. There’s something about going through drive-thru windows that brings out the best in Letterman and he’s even better with Zsa Zsa at his side. Some parts of the segment are staged but the chemistry between the couple is anything but artificial. Letterman loves having Zsa Zsa along for the ride. At Taco Bell, Dave pays for the car behind him and asks the attendant to say, “The tacos are on Zsa Zsa”—surely one of the best sentences in the English language.
The premise of this remote is hilarious even without any of Letterman’s comments into it. When a viewer named Colleen Boyle writes him a letter critiquing his casual footwear, Dave drives to her house in Hicksville, waits for her brother to come home, rifles through her shoe collection, ambushes her at her workplace (Sears), lets her pick out some new penny loafers for him, and then takes her out to lunch with his crew. Boyle’s uncontrollable giggling after meeting Letterman is equal parts irritating and endearing, and it’s exactly what makes the segment sing. Fun fact: Boyle was in Letterman’s audience earlier this month. He remembered her and took off his shoes for her at the top of the show.
“She’s gone already, chief.” It’s an immortal late-night line, said to Letterman by the Taco Bell customer in line after the one he’s scared away. Dave makes a difficult drive-thru attendant in this famous remote, refusing to get orders correctly and telling a disturbing anecdote about losing his toes in a riding mower accident when a woman simply asks how he’s doing. But it’s Dave’s impulsive offer to a customer to “come in and stick your head under the Pepsi machine” that’s the true marker of his absurd comic mind.
It’s not the remotest of remotes—like the hot dog segment, Dave filmed it from 30 Rock—but it’s one of the funniest. Out of mock jealousy for receiving a smaller promo poster than the “beach towel” NBC made for The Today Show’s prime time special, Letterman whips out a bullhorn and interrupts their live broadcast: “My name is Lawrence Grossman, the president of NBC News. This prime time program was my idea and I am not wearing pants!” Trying to bait the hosts with a hypothetical 150-year-old woman who needs to be wished a happy birthday is a particularly inspired touch. But Bryant Gumbel didn’t appreciate the interruption as he and Letterman feuded for four full years after the prank. (You can also watch the remote from The Today Show’s perspective here.)
The Taco Bell remote might have the most memorable one-liner but it’s Dave’s earlier three-part McDonald’s takeover that truly showcases his improvisational skills. When one customer tries to order, for example, he deadpans, “This is a car wash.” And when Letterman detects a hint of sadness in one customer’s voice, he latches onto it with laser focus: “Is everything all right at home?” Dave keeps pressing, asking if the customer is “pretty much happy with where [he is] in life,” and you can tell by his defensive “A number 3, all right?” that the answer is no.
When GE acquired NBC in 1986, Dave tried to deliver a fruit basket to his new corporate overlords—an obvious ploy to paint them as humorless suits. They played right into his hands. When an executive finally comes to the lobby, he refuses to shake Dave’s hand, violently grabs the microphone, and blocks the camera with his palm. Then GE security goes full stormtrooper on Dave’s crew, shouting, “We warned you once. Keep moving!” Dave will always be remembered for his irreverence and there’s nothing more irreverent than his ear-to-ear grin as GE tells him to get off their lawn.