YMMV / Late Night with Conan O'Brien

• Big-Lipped Alligator Moment: The "Comedy Spring Cleaning" sketch, since it's just Conan showing numerous unused clips without any context.
• Broken Base: Was the show better with or without Andy Richter? The former camp likes the chemistry between the two, but the latter camp enjoys the fact that, without anyone to bounce off of, Conan did a lot more improvising and ad libbing, which is one of his biggest comic talents.
• Ensemble Dark Horse:
  • James Worthworth, the drummer who replaced Max Weinberg for a couple weeks in 2004 while Max was recovering from a neck injury, as well as whenever Max toured with the E-Street Band. Not only was he (good-naturedly) picked on by Conan for not playing the opening drum roll just right, but the camera focused on Jimmy Vivino at the end of the opening song instead of the drummer as usual. This practice continued on Conan, where James had permanently replaced Max but Jimmy still gets the camera time.
  • For that matter, Jerry Vivino, Jimmy's brother, and Scott Healy, both of whom were rarely featured in sketches unless the entire Max Weinberg 7 was featured.
• Growing the Beard: Conan's first few years were very shaky, especially as he was a writer not used to performing in front of an audience or on camera. Conan was so unpopular that David Letterman, despite despising NBC, took it upon himself to send over audience members from his own show to fill Conan's studio. It wasn't around his third and fourth years that Conan began establishing his own unique identity and started growing an audience.
• Harsher in Hindsight:
  • In a 2001 interview, Tina Fey claimed that Bill Clinton's Monica Lewinsky scandal was the craziest that a presidency would ever get. Fey would become by far the most well-known impersonator of Sarah Palin, whose 2008 vice-presidential candidacy resulted in a media frenzy after her antics raised ever-increasing concerns that she was underprepared for the role.
  • A 2005 interview with Al Franken where he took glee in Bill O'Reilly's sex scandal is less funny after Franken himself had his own sexual harassment scandal in 2017 which led to him resigning from Congress.
  • In an interview with Greg Giraldo in 2005, he made jokes about prescription drugs. It may have been funny at one time, but it's uneasy to watch now, considering he died of a prescription drugs overdose in 2010.
  • One Celebrity Letters segment from 2003 had a thank you note from Robin Williams which was written in his usual hyperactive style and ended with, "...Kill me." Really uncomfortable nowadays, considering Williams committed suicide a decade later.
  • In December 2008, Conan did a "Live via Satellite" segment and interviewed "Arnold", like usual. The discussion came to Conan taking over The Tonight Show in 2009 and Leno moving back to 10 PM, to which Arnold exclaimed that Leno has mastered time travel. Arnold further stated that Conan needs to travel back in time himself and stop Leno from hosting the show. Makes you go "Oh wow" in light of the Tonight Show conflict.
• Hilarious in Hindsight:
  • In 1997, Conan took advantage of the Star Wars Special Editions being a hit by suggesting a 20th anniversary edition of Dirty Dancing. He would push it for weeks with clips from the film, talking of how great it was. Then, an actual re-release of the film was announced...at which point, Conan used the exact same clips to mock how stupid the movie was and "who asked for this to be released again?"
  • In 1997, when they did a sketch of future tombstones of celebrities, Bruce Springsteen's said "For the last time Max, no I don't think we're getting back together again". The E Street Band did a reunion tour in 1999, followed by more albums and tours.
  • One "In the year 2000" had Chris Rock deliver this punchline: "A black man will be elected president of the United States... oh I'm sorry, that's in the year 10,000!" Needless to say, he was way off. Not only that, but Rock himself would later star in a movie about a black man running for U.S. president (and winning), which, since it was made in 2003, would've made him the first black president.
  • On the February 19th, 2004 show, in the recurring sketch "New Stamp Designs", one of the series featured was Donald Trump's Daydreams, with the first part of the series being "President Trump", which came true nearly thirteen years later. See the full sketch here.
• Les Yay:
  • One "sweeps week" featured two women in the audience who made out with each other, for no other reason than it was sweeps week.
  • There was also the lesbian kiss that Triumph coaxed two elderly women to give each other when he went to the Tony Awards.
• Memetic Mutation:
  • "FOR ME TO POOP ON!" ^Explanation (Triumph the Insult Comic Dog's catchphrase)
  • "Did X die?"/"No, they're still alive." ^Explanation (whoever is in charge of Team Coco's Youtube channel uploads random celebrity interviews from various eras of the show. Since some interviews are uploaded to pay tribute to someone who recently died - see Norm Macdonald or Bob Dole in 2021 - people naturally assume that any video featuring a celebrity means that celebrity has recently passed away. This is especially true for older celebrities whom you could easily assume had died.)
• Nightmare Fuel:
  • "If They Mated," which takes two celebrities who appear in the tabloids (because they are, or at the time, were dating/hanging out with each other) and the audience finds out what their love child would look like. The results are a combination of this, Nightmare Face and Unintentional Uncanny Valley. It ventures out of those territories with the last two couples featured, since the result of those is another celebrity or on rare occasions, Conan himself.
  • The Skeleton Show. Mostly it's fine, although during Larry King's interview, the camera zooms in on Larry and Conan's eye-less eye areas for numerous seconds, which is quite unnerving.
  • Whenever Martha Stewart is "interviewed" on Live via Satellite, she will start off the interview congenial, but if Conan pries into her personal life or legal troubles, she'll suddenly get a demonic voice and demented eyes, sometimes with flames and ominous music popping up behind her.
• Signature Scene: Triumph sketches have two of them: First is his catchphrase ("For me to POOP ON!"), the other is Triumph humping real dogs.
• Special Effect Failure:
  • Triumph's arm, which is unnaturally long and completely detached from his body, which already happens to have four clearly visible limbs.
    Triumph: ...Let me fix my arm here. [Robert Smigel puts it back into place]
    Conan: He has trouble with his arm sometimes.
  • The "Live via Satellite" segments did this deliberately, with no illusion that it's a different mouth grafted over the celebrity faces. One notable instance of Special Effects Failure occurred when Conan interviewed Sammy Sosa about steroids in baseball: Sosa refused to comment on the scandal, and at one point, Robert Smigel (voicing Sosa) moved his head so that his mouth wasn't in the proper cut-out spot. He placed his right eye where Sosa's mouth was supposed to be, and said he had an eyeball in his mouth and couldn't talk.
  • In one "Conan and Andy on the Aisle", the duo accused Twister of this, and showed "footage" from the film to prove their point: A bunch of obviously green-screened actors reacting while they were pulled out of the frame.