David Letterman's 8 Best Pranks

Kate Erbland
David Letterman
Jeffrey R. Staab/CBS

The outgoing late-night host has always had a taste for a good gag. Here, some of David Letterman's best sneak-attack jokes.

Dave Interrupts The Today Show

What does it take to involve the seemingly mild-mannered Bryant Gumbel in a years-long feud? Yelling at him during a live taping of The Today Show, apparently. Back in 1985, Letterman was in the middle of his tenure as Late Night host, but he was still a bit of rabble-rouser around the NBC offices. The star demonstrated his keen ability to stir things up on an otherwise unremarkable August day, when he notoriously interrupted a live taping of The Today Show as it filmed on NBC's outdoor plaza. As hosts Jane Pauley and Gumbel staged an interview with Miami Vice stars Don Johnson and Philip Michael Thomas (who were actually doing the interview via video feed), Letterman cracked open a window in the RCA building, pulled out a bullhorn, and started shouting things at the filming show below. Gumbel didn't take too kindly to it, but the prank is arguably Letterman's best (and boldest).

Dave Works at Taco Bell

In 1986, Letterman decided to dabble in a summer part-time job as a deadpan Taco Bell drive-thru cashier. Most of his customers were mystified when the guy behind the microphone was so concerned about the strangest minutiae of their lives ("Are you Mexican?") and why he couldn't handle a seemingly simple order. Letterman's stamina is the true star here, and he never gets flummoxed, even when his Chalupa-hungry customers appear to be on the edge of a rage blackout. Years later, the late night host duplicated one of his signature gags with a stint working the windows at McDonald's, which was just as wild and just as weird.

Dave Has Fun With a Car in Los Angeles

Letterman, a notorious car guy, decided to use a vehicle for some decidedly offbeat endeavors in 1995. He took to cruising around Los Angeles in a swanky boat of a car, engaging a gaggle of well-meaning mechanics in a series of increasingly odd gags (like the aghast tow truck driver who watches Letterman taste "oil" hot out of the engine–it was really chocolate syrup) and eventually treating the citizens of LA to a taco lunch. Cars really are fun!

Dave and Lindsay Lohan Prank Call Oprah

"Uh, this is Oprah!"

Letterman's 1995 Oscar hosting was roundly panned, mostly due to his infamous "Uma, Oprah" joke, which fell flat with the audience and took years to live down. By 2014, however, he was comfortable enough with the entire thing to prank call Oprah herself, alongside guest Lindsay Lohan. Sure, sure, the "prank" portion of the joke petered out pretty quickly–Letterman admirably imitated Lohan's assistant for about one line before falling sway to Oprah's confusion, but the entire thing was so strangely charming and lovingly low-key that it became an instant classic.

The Hose Cam

Letterman frequently engaged random strangers who just happened to stroll by the Late Show's New York City studio. During a particularly brutal summer last year, Letterman installed a hose cam to monitor pedestrians, talk to them via speaker, and ultimately cool them off with a generous water dousing. Of course the giant hose is hilarious, but the best part is Letterman's endearingly strange interactions with everyday people as they simply walk by and are spoken to by a strange voice from the sky.

Dave and Rupert Annoy People

The Hello Deli next door to Letterman's studio serves snacks and hot coffee, as well as a variety of Letterman apparel, all presented with a (relative?) smile from owner Rupert Jee. In 1995, the sardonic Jee hit the streets as a cafe worker and a magazine stand vendor, with Letterman feeding him lines meant to relentlessly annoy customers and bystanders.

Dave Does Billy On The Street

The comedian still displays a hearty interest in the new generation of performers. Screechy-voiced and endlessly energetic Billy Eichner appears to thoroughly delight Letterman each time he appears on the Late Show. For Eichner's final  appearance, the duo hit the streets of Manhattan using Eichner's "on the street" method of engaging with strangers, screaming at them, and moving right along. Letterman relished the bit, but probably not as much as the gobsmacked pedestrians he and Eichner gleefully baffled.

Dave Scares Kristin Chenoweth

On the show last year, Kristen Chenoweth shared a story with Letterman about a terrible injury she sustained on the set of The Good Wife, thanks to a falling light fixture. Not exactly the best start for a gag, right? Chenoweth, however, seemed to be sufficiently recovered, and as she shared with Letterman hew newfound desire to constantly look up – and thus avoid more falling stuff – a giant bag fell from the rafters and right on to Letterman's desk. Chenoweth jumped about a mile, but even she couldn't contain her laughter.