History YMMV / LateNightWithConanOBrien

** In 1997, Conan took advantage of the ''Franchise/StarWars'' Special Editions being a hit by suggesting a 20th anniversary edition of ''Film/DirtyDancing''. 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 [[HypocrticalHumor the exact same clips]] to mock how stupid the movie was and "who asked for this to be released again?"

** "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, NightmareFace and UncannyValley. It ventures out of those territories with the last two couples featured, since the result of those is another celebrity or on rare occasions, [[SelfDeprecation Conan himself.]]

* FunnyAneurysmMoment:
** 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 [[https://youtu.be/oLOa7Kv5OwU?t=289 here]].
** Similarly, in a 2001 interview, Tina Fey claimed that Bill Clinton's Monica Lewinsky scandal was the craziest that a presidency would ever get. Yeah, she was wrong. Even ignoring Trump, there's the fact that Fey would become by far the most well-known impersonator of UsefulNotes/SarahPalin, 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 Creator/RobinWilliams which was written in his usual hyperactive style and ended with, "...Kill me." ''Really'' uncomfortable nowadays, considering Williams committed suicide a decade later.

* HarsherInHindsight: 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 [[https://en.wikipedia.org/wiki/2010_Tonight_Show_conflict Tonight Show conflict.]]
* HilariousInHindsight: 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, [[UsefulNotes/BarackObama he was way off.]] Not only that, but Rock himself would later star in [[Film/HeadOfState 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.