Never let it be said that CBS isn’t sending David Letterman into retirement in style. The outgoing Late Show host will be the subject of a 90-minute primetime special on May 4 that reflects on his multi-decade broadcast career. Hosted by Ray Romano, David Letterman: A Life on Television will include his pre-CBS days, while primarily covering his 23-year stint as the face of the network’s late night line-up. That means lots of opportunities to revisit some of the classic moments from the show’s run. As the producers of A Life on Television ready their tribute for air, here are our suggestions for memorable Late Show clips that must be included.
Make a Run for the Border (1996)
Customers at a New Jersey Taco Bell found that they had a particularly difficult time ordering their drive-thru burritos one fine summer day, thanks to the outlet’s newest employee. Whether he was denying one woman diet soda or complaining about his bad weekend, Letterman made sure to make everyone’s day a little more interesting.
Hop to It (1997)
To commemorate tax season, Letterman posed a particularly important question: How many guys in bunny suits can get into an H&R Block? As it turns out, not very many. At least… not in New York.
Everybody’s Got a Healthy Heart (2000)
The world watched nervously as Letterman prepared to broadcast his first show since undergoing quintuple bypass surgery. But the host took the stage without missing a beat. “Wait ‘til you hear what happened to me!” he told the cheering crowd. “After what I have been through, I am just happy to be wearing clothing that opens in the front.”
Paris Is Burning (With Embarrassment) (2007)
Rather than beat around the bush, Letterman cut right to the chase in his interview with the Simple Life socialite, who had served a 45-day jail sentence earlier in the year. Quizzing her about every aspect of the experience, from the bad food (like the bologna sandwiches) to what she learned about herself. Note to the Robert Downey Jr. guy — this is how you ask a celebrity about their questionable past life choices.
Phoenix Rising (2009)
Like much of the nation, Letterman was unwittingly a pawn in Joaquin Phoenix’s intensely method performance for the mock-documentary, I’m Still Here, where he professed to be retiring from acting in favor of a rap career. Shambling onstage with a bushy beard and a disaffected attitude, Phoenix baffled the usually unflappable host. When he returned to the show five years later, he appeared to be in a better headspace, even announcing his engagement to his yoga instructor. Except, once again, he wasn’t on the level. The next day he admitted that he made the whole thing up because he felt his ordinary life was “boring.”
Cannon Fodder (2015)
As part of Letterman’s regular “On 53rd Street” feature, he shut down the stretch of 53rd Street outside the Ed Sullivan Theater to shoot Gemma, a professional human cannonball, out of a cannon. She flew for 100 feet, some 40 feet up in the air as onlookers snapped photos and Letterman narrated the play-by-play in studio. Perhaps that’s the next act of his career: circus announcer.
David Letterman: A Life on Television will air May 4 at 9:30 p.m. on CBS.