History HilariousInHindsight / SaturdayNightLive

For every FunnyAneurysmMoment on ''Series/SaturdayNightLive'', there are at least a couple of HilariousInHindsight moments that make the sketch funnier years after the sketch aired. Some examples:

** Creator/MayaRudolph makes a surprise appearance as Senator UsefulNotes/KamalaHarris, sarcastically saying it would be terrible if Biden dropped out of the race, which works twofold: It was Harris who dropped from the race before even reaching the primaries, while Biden won the nomination... and then Biden picked her as his running mate.

* While it's very much a [[FunnyAneurysmMoment Funny Aneurysm]] or HarsherInHindsight moment to liberal/left-wing viewers, the jokes made about Donald Trump losing the election to UsefulNotes/HillaryClinton, when it was expected she would win, can come off as this to supporters of Trump, since he actually won the election.
** Worth noting at this point is that Creator/LinManuelMiranda's "never gon be president now" chant is from "Reynolds Pamphlet", the part of ''Theatre/{{Hamilton}}'' where Hamilton's infidelity was made public... something Trump is well familiar with by now.

* In 1978, Creator/CarrieFisher, playing Princess Leia, appears in a sketch [[Film/ReturnOfTheJedi wearing a gold bikini]] at the beach.

* The Kim Kardashian episode features an ''WesternAnimation/{{Aladdin}}'' sketch, with Kardashian as Jasmine and Pete Davidson as a self-conscious Aladdin. The climax of the sketch sees the two of them making out. Weeks later, both Kardashian and Davidson were spotted holding hands, which drove social media into a frenzy over the possibility of themd ating, which they confirmed several weeks later.

* The Kim Kardashian episode features an ''WesternAnimation/{{Aladdin}}'' sketch, with Kardashian as Jasmine and Pete Davidson as Aladdin, and both kiss near the end. Weeks later, both Kardashian and Davidson were spotted holding hands, which drove social media into a frenzy and there was speculation of them dating, even after a source said they were "just friends".

* All the times Al Franken played a U.S. Senator, including a 1991 Clarence Thomas skit in the Creator/KirstieAlley episode in which he was Sen. Paul Simon, became this since he became a U.S. Senator for real.

** The appearance of both Hawkman and Hawkgirl, the latter of whom was pretty obscure at the time, but ''Series/LegendsOfTomorrow'' made sure to do the same.

** Aquaman shows up with a plate full of shrimp - in ''Film/JusticeLeague2017'' it's Aquaman bringing fish to the hungry that leads Batman to find him.

** Tim Meadows plays the then-obscure John Stewart Green Lantern, long before the ''WesternAnimation/JusticeLeague'' cartoon would make him the best-known one.

** Al Franken plays Lex Luthor, both of whom have famously been involved in politics.

* [[https://www.youtube.com/watch?v=suotMy3uYG8&ab_channel=SaturdayNightLive This cold opening]] from the 12th episode has Tim Meadows as O.J. Simpson quoting Cuba Gooding Jr's "Show me the money!" line from ''Film/JerryMaguire''. Gooding would then go on to play O.J. in ''Series/ThePeopleVOJSimpson''.
* This season featured the first ''Celebrity Jeopardy!'' sketch where the contestants are complete airheads who can't even get a single question right. On the Creator/MartinShort episode, Creator/BurtReynolds (Creator/NormMacdonald) doesn't remember that he was in ''Film/TheCannonballRun''. 13 years after this episode, Kareem Abdul-Jabbar got his own line from ''Film/{{Airplane}}'' wrong on a real CelebrityEdition of ''{{Series/Jeopardy}}''.

* During the 25th anniversary special (broadcast in 1999 before the beginning of Season 25), a ''TV Funhouse'' short [[SelfDeprecation mocking Lorne Michaels]] showed him, among other things, advertising some SNL merchandise. One of the products he present is the fictitious 45th anniversary special [[UsefulNotes/{{VCR}} VHS]] [[TechnologyMarchesOn tape]], with a future appearance of Wayne and Garth, and Music/PaulSimon as a musical guest, all of them very, very old-looking. Fast forward to 2015 and the real 40th anniversary, that included indeed a Wayne's World skit, and an aged Garth looks very similar to the animated depiction of the 25th anniversary (Wayne not so much); Paul Simon don't look as decrepit as in the cartoon, but the song he sings is the same: "Still Crazy After All These Years".

* In a 2002 episode hosted by Senator John [=McCain=], one sketch features [=McCain=] playing himself appearing on ''Meet the Press'', and maturely swatting down attempts by Tim Russert (Darrell Hammond) to have him announce running for president again [[note]][=McCain=] had previously run as a candidate in 2000[[/note]], saying that he's not interested. Of course, we all know he later became the Republican nominee in 2008...

* In an episode where Kanye West was a musical guest, he had a guest role in a sketch in which he interrupted various awards shows to say that he should've won (including the Nobel Prize and a county fair pumpkin competition). Just two years later, West would bring down a huge controversy upon himself when he interrupted Taylor Swift's 2009 VMA acceptance speech to say that Beyonce should have won instead, and he has yet to [[NeverLiveItDown live down that reputation]].

* The Taylor Swift episode had a fake commercial advertising the all-star soundtrack to an animated movie called ''Bunny Business'', including Swift as Music/{{Shakira}}. In 2016, Shakira would sing the theme song for [[WesternAnimation/{{Zootopia}} an animated movie]] starring a bunny.

* In the Alec Baldwin episode, Andy Samberg starred in a Digital Short called "[[https://www.youtube.com/watch?v=WRu_-9MBpd4 Great Day]]", a parody of "Zip-A-Dee-Doo-Dah" about a once-successful man whose spiraling addiction to cocaine has ruined his life, lost him his job, and alienated his family. Jump forward to 2015, where Andy Samberg -- now cast as Detective Peralta in ''Series/BrooklynNineNine'' -- spends an episode being held hostage by a once-successful man whose spiraling addiction to cocaine has ruined his life, lost him his job, and alienated his family. And to make it better, the addict in ''Brooklyn Nine-Nine'' is played by Chris Parnell, who also featured in the Digital Short "Lazy Sunday", which put Samberg on the map in the first place.

* During the SNL Digital Short in the Creator/GwynethPaltrow[=/=]Music/CeeLoGreen episode, Andy Samberg asks Anderson Cooper if he ever "got freaky with Barbara Walters". Cooper's response is along the lines of "Are you insane?" The joke when the episode first aired was funny because Andy was drunk off his ass, but now that Anderson Cooper revealed that he was gay, it makes Andy look like an idiot.
* Gwyneth appears in the Secret Word game show, partnered with Kenan who plays a urology professor who tells his students on live TV that they will have a quiz on asparagus. It's a little funny considering that Gwyneth's Goop lifestyle company would later have a NeverLiveItDown reputation for its emphasis on feminine hygiene.

* In the "It's a Date" sketch, the [[Music/TheLonelyIsland Dick in]] [[Music/JustinTimberlake a Box]] duo are one of the bachelors in the show and both answer a question about how a night at home in the rain with them would go by watching ''WesternAnimation/DuckTales''. What makes it funnier is that one of the bachelors is played by Creator/BobbyMoynihan who would eventually voice Louie in [[WesternAnimation/DuckTales2017 the 2017 reboot]].

* One sketch featuring potential auditions for ''WesternAnimation/LionKing2019'' featured Creator/JohnOliver as Zazu, before Oliver was ''actually cast'' as Zazu for the film in real life.

* In a spoof of ''Series/TheCarrieDiaries'', the show features a fake trailer for ''The Sopranos Diaries'', with Tony Soprano and his buddies as high-schoolers. Fast-forward to 2021, and we have ''Film/the many saints of Newark.''

* One "What If...?" sketch exploring "What if Franchise/{{Superman}} was raised in Nazi Germany?" becomes a lot funnier thanks to ''ComicBook/FinalCrisis'' introducing one alternate universe Superman named Overman who was raised by the Nazis. To a lesser extent, there's also ''ComicBook/SupermanRedSon'', an Elseworlds story where Superman was raised in the USSR. Also, Nazi-Superman's alias is "Uberman", which becomes funnier if you've ever read ''ComicBook/{{Irredeemable}}'' or ''ComicBook/{{Uber}}.

* During ''Undercover Boss: Starkiller Base'' in the Creator/AdamDriver episode, [[Film/TheForceAwakens Kylo Ren]] (disguised as "Matt") [[ButHeSoundsHandsome claims that Ren has an eight-pack and is shredded]]. Come ''Film/TheLastJedi'', and as it turns out, ''he's not lying.''

* Matt Foley, who lives IN A VAN DOWN BY THE RIVER, was said to be vindicated when in TheNewTens [[https://en.wikipedia.org/wiki/Vandwelling people started living in vans]], with even [[Film/{{Nomadland}} an Oscar winner built around the lifestyle]].

* The cold open for the last April sketch before the month-long break had two black news-anchors (Kenan and Ego) have tepid expectations for the results of the Derek Chauvin trial in comparison to the two white anchors (Kate and Alex,) even going as far as to say "we've seen this movie before." Well, they luckily hadn't this time, because he was found guilty on all three charges.

** ComicBook/BlackLightning (played by host Creator/{{Sinbad}}) is so obscure he's turned away at the door. [[Series/BlackLigtning2018 Not so much now that he has an Arrowverse series.]]

For every FunnyAneurysmMoment on this show, there are at least a couple of HilariousInHindsight moments that make the sketch funnier years after the sketch aired. Some examples:

* In the end of the first episode of this season, Creator/ElliottGould introduces the new cast one more time and proudly tells the audience, "We're gonna be around forever!" [[FunnyAneurysmMoment Three months later, another host, Charlene Tilton, caused an F-bomb debacle which got most of those cast members fired as a result except for EddieMurphy and JoePiscopo]], but it also counts as this trope ''and'' HeartwarmingInHindsight considering that SNL is still the [[LongRunner longest running]] sketch show.

* In the end of the first episode of this season, Creator/ElliottGould introduces the new cast one more time and proudly tells the audience, "We're gonna be around forever!" [[FunnyAneurysmMoment Three months later, another host, Charlene Tilton, caused an F-bomb debacle which got most of those cast members fired as a result except for Creator/EddieMurphy and Creator/JoePiscopo]], but it also counts as this trope ''and'' HeartwarmingInHindsight considering that SNL is still the [[LongRunner longest running]] sketch show.

* In the end of the first episode of this season, Creator/ElliottGould introduces the new cast one more time and proudly tells the audience, "We're gonna be around forever!" [[FunnyAneurysmMoment Three months later, another host, Charlene Tilton, caused an F-bomb debacle which got most of those cast members fired as a result except for Creator/EddieMurphy and Creator/JoePiscopo, but it also counts as this trope ''and'' HeartwarmingInHindsight considering that SNL is still the [[LongRunner longest running]] sketch show.

[[folder: Season 15]]
* Music/SineadOConnor was scheduled to perform in the penultimate episode, but she pulled out of the episode due to the controversial choice of host (Creator/AndrewDiceClay). This is amusing given that she herself would spark controversy on the show later on by ripping apart the Pope's picture while identifying him as "the real enemy." She performed on the next season's premiere (which is, by the way, NOT the infamous performance stated above).