Funny / The Late Show with David Letterman

Let's face it, the ENTIRE FREAKING SHOW can be considered this. But there were a few moments that go beyond this.

• ANYTHING involving Calvert Deforest.
• When Regis Philbin came out dressed as Shrek. What was funny is that he didn't even bother to act in character, but instead griped about how long it took to get the make-up applied. Letterman's interjections were great too, suggesting that he and Shrek go "get a couple of whores" ("Regis would probably say no, but Shrek is ready!") and interrupting Regis's plug to say "Who cares?"
  • Similar to the above, one episode saw Elaine Stritch, who wasn't even scheduled as a guest, repeatedly coming onto the stage and talking to Dave as if he was her new pool boy. Dave remained perfectly in-character as oblivious as Stritch made bizarre non-sequiturs, hit on him, and eventually ended their "relationship."
• The last episode of his run of the Late Show opened with Gerald Ford saying "Our great national nightmare is finally over." A line that was echoed by George H. W. Bush, Bill Clinton, George W. Bush, and President Barack Obama.
• Chris Farley's appearances on the show were filled to the brim with high energy, but the one time he appeared had him make a rather EPIC entrance in which he picked up an audience member and and ran outside the studio, shortly before throwing said audience member IN A DUMPSTER.

• When he interviewed the 2013 Indianapolis 500 winner Tony Kanaan, they brought out the Borg-Warner trophy (a giant trophy commemorating all the Indy 500 winners) to show everyone. Dave and Tony realize that they'll never get a chance to be this close to it without security nearby again....so they start touching it all over, capping it with Tony hugging it.
• One odd sequence has Dave bragging about his supposed psychic abilities. A flashback sees him sitting in an office, then suddenly looking up and crying "Oh my God, PAUL'S ON FIRE!" He runs up the stairs and douses Paul with a giant bucket of water; Paul, who is clearly not on fire, takes umbrage. And then, directly outside Paul's office, a different man spontaneously combusts.
• Dave's "cut scene" from the latest Transformers movie, which consists of him standing in the break room and yelling that a toaster is a Transformer that wants to kill him. An annoyed woman tells him he's being stupid; once she leaves, the toaster sprouts a laser and does kill Dave.
• Biff Henderson, who had no acting experience, was frequently prevailed upon to do odd things in public. The resulting spots were pure gold. Highlights include "Biff Henderson's Fun with a Stopwatch," which featured Biff timing how long it took for things to happen: the list included how long it took someone to comment on a giant sombrero he was wearing, how long he could eat mints at a diner's counter before someone made him stop (the kicker—no one ever did), and how long he could read over someone's shoulder before they asked him to stop (in this example, Biff ends up stealing his target's newspaper and eventually walking away; the guy doesn't say anything). In another "Celebrity Lookalike" segment, Biff wanders around and compares passerby to famous individuals; at one point, he approaches a gigantic tattooed man and remarks "I don't know who you look like, but you scare the [bleep] out of me."
• Speaking of Regis, his top 10 list "Top Ten Signs Regis Philbin is Nuts":
  #10: He's actually gone on one of those lame Carnival cruises.
  #9: Keeps showing up for work in full Cats makeup.
  #8: One minute you're having a civilized conversation and the next minute the old coot's on the floor doing push-ups.
  #7: Richard Simmons found smothered under a two-ton pile of Regis's workout videos.
  #6: Now kicks off each morning show by biting head off chicken.
  #5: Claims the CIA has been sending satellite beams into his pants.
  #4: Last week spotted naked in Central Park with bottle of scotch screaming, "Where's Gelman?"
  #3: Never changed his weird-ass name.
  #2: Every couple of years, just for fun, he switches Kathie Lee's birth control pills with Tic Tacs.
  #1: Come on, look at the guy.
• In a 1999 episode, one viewer letter asked Dave if he was going to see the Pokemon movie this weekend. That's funny in itself, but then Dave invited the creator of Pokemon out to explain the franchise, with the twist that it was some bearded white guy playing Satoshi Tajiri.
• Every one of Robin Williams' appearances. Particularly in February 2000, shortly after Dave's heart surgery. Robin showed up wearing surgical scrubs.
  • Robin participated in one of the "Alan Kalter's Celebrity Interview" skits and ends up hijacking it by shouting Spanish into the microphone. Paul and the band roll with it, playing Latin dance music:
  Robin Williams: DAVID LETTERMAN ES MUCHO! ESTO NUMERO UNO!!!
• One of the interviews with Paris Hilton. He wasn't really interested in discussing her new fragrance, but was fascinated with her brief stint in jail and kept asking her questions about it, even after she wanted to move onto a different topic.
• Jay Thomas's famous "Lone Ranger" story. To go into more detail: when Thomas was a young radio DJ, he worked a gig at a used car lot featuring an appearance from Clayton Moore, the most famous Lone Ranger who ever donned the mask. He and a friend went behind a dumpster to, in his own words, "get herbed up," and were then tasked with driving Moore back to his hotel. During the ride, a jerk damaged Thomas's car and drove away, prompting the two to give chase (with Moore sitting silently in the back seat, still in full Lone Ranger gear). When they finally cornered the guy, he started accusing them of hitting his car, and sneered that the cops would clearly side with him: "Who are they gonna believe—me, or a couple of hippie freaks?" And that's when Moore opened the door, strolled out, and declared "They'll believe ME, citizen." The shocked driver immediately apologized: "I'm sorry, I didn't know it was you." Letterman openly declared this "the best talk show story ever," and made it a tradition to have Thomas on the show every year at Christmas time (in the same episode featuring Darlene Love's famous annual rendition of "Christmas, Baby Please Come Home") to tell it.
  • Even better—there was one year toward the end of the show's run where Thomas was unable to make the appearance. Not to be outdone, tennis legend John McEnroe showed up instead, having memorized the story beat for beat, and told it perfectly.
• One of the last major guests Letterman had on the show was then-New Jersey governor Chris Christie, who'd be a target of Dave's jokes (especially about his large size) for some time. The interview was quite funny, but it was Christie who pulled one over on Dave—when Letterman started to ask about how the governor felt about the fat jokes, Christie, without missing a beat, reached into his pocket, pulled out a doughnut, and started eating it on camera while remarking "I didn't know this was gonna be this long." Dave burst out laughing and needed some time to regain his composure.
• This bit in the Don Rickles interview from 2013 while discussing Regis Philbin:
  Don: He's a wonderful- and his wife's on, too.
  David: (stuttering) His wife-
  Don: How long have you had that? "D-d-d".
  David: I didn't realize his wife-
  Don: Hey gang, I'm on a million shows, I never had a host go "D-d-d-d"!
• Joaquin Phoenix appearance in 2009 while promoting Two Lovers. He had sunglasses with a full beard and appeared uninterested in being there. Talking about going into rap and leaving acting. Letterman goes into the interview like normal, with Joaquin Phoenix giving short answers and acting like he has no clue what his movie is about. Letterman then starts being snarking, with references to Joaquin dressing like the Unabomber and how he can't seem to walk and chew gum at the same time. While later on it revealed that it was a hoax, with Letterman in on the joke, it still a site to behold with the final part of the interview summed up by Letterman.
  David: Joaquin, I'm sorry you couldn't be here tonight.
• Whenever Bruce Willis was on the show, where he would mix his action film style with comedy.
  • One episode had Bruce jump off the building into a pool. Earlier in the show, Letterman had dogs jumping into a pool to measure their distance. Bruce figured this would be the perfect time to jump off the building into the pool below. So during the interview, he declared he wanted to do it and ran to the roof and jumped off. Missing the pool and landing on the sidewalk below, ending the interview.
  • Another episode, Letterman was thanking his interns for a job well done and Bruce Willis was one of the interns. He brought along a video of his time working. The clip had Bruce acting as John McClane but with everyday office issues. Such as running around yelling at everyone that the copier was almost out of toner; trying to figure out the which button to push on the cooler, the red or blue button, as if he was trying to disarm a bomb before being informed by another intern that it was just if he wanted hot or cold water. His final clip is where he went into a conference room and killed the intern who was bringing donuts to the employees. He said sorry to Dave for killing him.