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David Letterman’s last episode of The Late Show shall air on May 20. This marks the end of a three-decade career in late night talk shows. Are you dreading the end of Dave as we know it? Let’s usher in some serious nostalgia with this list of Dave’s most memorable guests.
1. Drew Barrymore (1995): Once upon a time, Drew was a very wild child. Right around the time she posed for Playboy, Drew paid a very memorable visit to Dave. She spoke about how much she loved stripping and then illustrated her point by hopping onto Dave’s desk and delivering an eyeful. The look on Dave’s face was priceless.
2. Howard Stern (2006): Stern looked fabulous in drag to promote his hop over to Sirius radio, and his larger than life persona carried over well from radio to television. However, Stern didn’t get away with everything during this visit. Stern tried to reenact Drew Barrymore’s famous dance, but Dave couldn’t take it. He hilariously left the room.
3. Paris Hilton (2007): Fresh out of jail, Paris made the bizarre decision to publicize her freedom with a visit to Dave. Officially, Paris was on hand to promote a new perfume called “Can Can,” but that’s not what Dave wanted to discuss. He went hard right out of the gate, asking, “How’d you like being in jail?”
4. Kristen Stewart (2008): This stands as one of the most awkward interviews in Late Show history. Stewart was on tour to promote the first Twilight movie. She’s never been comfortable during talk show interviews, and Dave wasn’t impressed by her lack of enthusiasm. After a few minutes, he’d had enough: “You and I couldn’t be more different.”
5. Sacha Baron Cohen (2006): Letterman didn’t seem amused when Cohen showed up as his Borat character. Cohen proceeded to hand out endless Borat-isms, including the “disco dance” and the desire to “take photos of ladies when they make toilet.” The worst part? When Cohen exclaimed, “My wife is dead. High five!”
6. Lindsay Lohan (2013): When Lohan showed up to promote Scary Movie 5, Letterman ribbed Lohan for her repeated stints in rehab. He cracked jokes about her alleged shoplifting and nightclub brawls. Lohan held her ground surprisingly well.
7. Andy Kaufman (1980): Perhaps the most notorious Letterman visit of all occurred when Kaufman delivered this highly bizarre interview. He stared into space, coughed dramatically, and wandered into the auditorium to collect spare change from bewildered audience members. Dave was certainly in on the joke.
8. Joaquin Phoenix (2009): We now know that Phoenix used this appearance to try and “pull a Kaufman” as he announced his retirement from acting and budding rap career. The main problem? Letterman was not in on this joke, and he wasn’t pleased about it. In 2010, Phoenix returned to the show and apologized for pulling one over on Dave.
9. Jennifer Lawrence (2013): This visit was a positive one. It stands as an excellent example of rapport that Dave could develop with repeat guests. He and Jen cuddled under a blanket together and commiserated over bad haircuts, digestive ailments, and exhausting schedules.
10. Madonna (1994): After this notorious visit, Madonna didn’t return to Dave-land until 2000. Perhaps her agents warned her against making such a public spectacle outside of a concert venue. Madge dropped the F-word 14 times and teased Dave with sexual jokes. Never before or after has a talk-show appearance appeared so relentlessly bleeped.
11. Crispin Glover (1987): This guy revealed his true degree of weirdness while promoting River’s Edge. Glover showed up wearing an obvious wig and an outrageous 1970s ensemble. He challenged Dave to an arm-wrestling match. In 2012, Crispin refused to speak about the incident: “I can neither confirm nor deny that I was ever on the David Letterman show.”
12. Chris Rock (2009): This visit took place in the wake of Letterman’s extortion case, which forced him to reveal an affair with his former assistant, Stephanie Birkett. Rock was perhaps the only one who could deliver such a merciless takedown of Dave (to his face) and get away with it. This was a truly memorable segment.
13. Farrah Fawcett (1997): Nobody knows what was wrong with Fawcett during this visit, but she was likely operating under the influence of drugs or alcohol. Fawcett was on hand to promote her Playboy cover, but she showed up late due to “people, lots of people.” Then she paused for a moment while looking at the stage backdrop: “Wow. I really thought I was looking out the window.”
14. Lady Gaga (2011): She’s the master of manufactured controversy, and Gaga managed to disturb Dave by ripping up his host notes. Then she shoved a ball of paper in her mouth and maniacally chewed away. Dave tried to talk Gaga into spitting out the paper: “That’s not what you think… It’s chemically treated. You’re going to be sick for weeks.”
15. Bill Murray (1982): After dozens of hilarious visits, it’s almost impossible to pick the most memorable time Bill Murray visited Dave. He often shows up in costume and pulls all manner of pranks on the audience. This visit was the first one following Dave’s switch to NBC. Murray is scheduled to be one of Dave’s last guests next month, so tune in for awesomeness.
Finally, let’s not forget Harvey Pekar’s Letterman appearance.