"Funny Aneurysm" Moment and Harsher in Hindsight: A lot of past sketches are harder to look at (and laugh at) now due to cast member deaths, host deaths, or the "prediction" of a horrifying/tragic/controversial event that was once played for laughs and not thought to be real at all. Examples:
The infamous "Don't Look Back in Anger" short film that showed an elderly John Belushi as the last living member of the original "Not Ready for Primetime" cast who ends up dancing on his cast mates' graves. (What's more disturbing is that the short film "predicted" that Gilda Radner would be one of the dead cast members)you can watch the clip here.
The worst part is Belushi's comment that "they all thought [he'd] be the first to go" (a reference to his then already well known excessive lifestyle).
Oh, and John "died" at the end of "Wolverines," the very first sketch in the very first episode. So did Michael O'Donoghue.
A lesser known example from the "Not Ready for Prime Time" era is in a sketch known as "Least-Loved Bedtime Stories." Michael O'Donoghue narrates a story called "The Little Engine that Died," where he says "I think I can...I Think I Can...HEARTATTACK...OHMYGODTHEPAIN!" In 1994, "Mr. Mike" woke up, felt what was thought to be a severe migraine headache, and screamed "OH MY GOD" in pain and later died from cerebral hemorrhage. Michael O'Donoghue was an SNL writer known for his sadistic humor and his frequent migraines, making this death a literal "funny aneurysm moment" and a Karmic Death.
On season 5 (the 1979-1980 season), Strother Martin hosted SNL. One of the sketches he was in was about a dying man who recorded a video will. In August of 1980, Strother Martin died, not only making the episode he hosted (Martin's last acting gig, mind you) a Missing Episode, but making the video will sketch a lot less funny.
Any time Chris Farley faked a heart attack during the Chicago Superfans sketches. Also, the one-off sketch where Farley plays a man called "The Relapse Guy" who keeps going on and falling off the wagon.
The final sketch on the season 19 finale hosted by Heather Locklear where Phil Hartman, in his last episode as a cast member, sings "So Long, Farewell" to Chris Farley. It was meant to be sweet and signal the end of the season, but with both Farley and Hartman dead (within 6 months of each other!), it's now too depressing to watch.
On the season 11 premiere hosted by Madonna, there was a cold opening where then-NBC executive Brandon Tartikoff announces that he's subjecting the 1985-1986 season cast to mandatory urine tests for drugs (this sketch was later Edited for Syndication, as the censors in the 1980s thought that the idea of urine testing was too taboo for late-night TV at the time — never mind that ''SNL'' is supposed to be the vanguard of edgy, late-night TV humor). One of the cast members during the 11th season was a 20-year-old Robert Downey, Jr., who would later spend all of the 1990s being more well-known for his drug abuse and arrests than his movies (though it was playing drug addicts that got Downey, Jr. back into stardom in the 2000s. Go figure).
When Phil Hartman came back to host for the second time (in season 22 — the 1996-1997 season), he says in his monologue that he bought his family's affection with the money he makes from being on "NewsRadio" and "The Simpsons." Apparently, it didn't work, when you consider what happened to Hartman a few months after he hosted.
The episode hosted by Charlize Theron on the 2000-2001 season had a cold opening called "A Glimpse into Our Possible Future," a sketch showing what would happen to America if George W. Bush were President (and later, if Al Gore were President and if Ralph Nader were President). While the sketch did exaggerate how far George W. Bush (played by Will Ferrell) would run America into the ground (like setting the Great Lakes on fire or giving Texas to Communists), lines like, "I hope I get a war. Wars are like executions supersized," and "I killed Dick Cheney in a hunting accident" (and the fact that his new map of the United States shows several flooded states starting in Louisiana and pooling in the Midwest and California as a flaming wreck) now don't seem so funny.
On the Seth Rogen/Phoenix episode from season 34, Seth Meyers (the Weekend Update anchor) did a report on how during Michael Jackson's summer world tour, he would bring his son onstage, who would be accompanied by a police officer who would have Michael Jackson arrested. Unfortunately, the concert (and the punchline to the joke) would never come to pass due to Jackson's death two months after the episode originally aired.
Then there's that SNL Digital Short where Bill Hader plays a man who writes a letter to his sister and his friend (played by Andy Samberg) shoots him, leading to the shooting deaths of another man (played by episode host Shia LaBeouf), the sister (played by Kristen Wiig), and two police officers (played by Fred Armisen and Jason Sudeikis). Two days after the sketch aired, the shooting at Virginia Tech happened, which was one of two reasons why the sketch never appeared on NBC's Saturday Night Live web page, which has video highlights of past and present sketches (the other reason being that NBC never cleared the copyright to the song used in the sketch). What a shame that everyone overreacted to a simple parody of The O.C.. As it was, the short became one of the first from the show's to be unofficially popularized on YouTube. Memetic Mutation followed; the Imogen Heap song which SNL couldn't get cleared has now been sampled for a hip-hop beat.
The SNL episode from season 35 hosted by Blake Lively from Gossip Girl had a Weekend Update segment where Abby Elliott plays a looped-out Brittany Murphy who thinks she's hosting SNL with musical guest blink-182 (Quick note: Brittany Murphy actually did host SNL during its 28th season in 2002, only the musical guest was Nelly, not blink-182). The Blake Lively episode aired on December 5th, 2009, fifteen days before the real Brittany Murphy would suddenly die of cardiac arrest. Because of this, Hulu.com pulled the video of this segment and the NBC TV rerun of this episode does not include this part.
Here's one that doesn't involve death, but still became controversial after the fact: On the Anne Hathaway/The Killers episode, there was a sketch about the assorted deadbeats and greedy people who would benefit from the economic bailout at the time. One of the people was a couple by the name of Herbert and Marion Sandler (played by long time cast member Darrell Hammond and 2-year feature player Casey Wilson), who screwed Wachovia Bank out of a lot of money and personally thanked the Congress for not holding them responsible for their corrupt activities. Who would have guessed that Herbert and Marion Sandler were an actual couple that actually did this (according to show creator Lorne Michaels, he and the other writers had no clue about this until after the sketch aired)? Because of this, the Internet video version of the CSPAN Bailout sketch and the NBC rerun of the Anne Hathaway episode edited out the entire part with the Sandler couple. The Netflix version does keep the part, but the lower-third caption describing the Sandlers as "People who should be shot" and Herbert Sandler (Darrell Hammond) thanking the Democratic Party for letting them get away with what they've done were removed (the edits are obvious, but not as blatant as removing the entire scene with the Sandlers, like on the television and Internet versions).
When Al Gore hosted a Christmas episode in season 28 (2002-2003), the monologue showed how Al Gore picked his running mate, rejecting John Kerry (Seth Meyers) and John Edwards (Will Forte). Gore then remarks that "one of them would make a great Vice President someday." Kerry and Edwards would team up to run for President and Vice-President in 2004, only to be beaten by Bush and Cheney (who were running for re-election). Depending on your political leanings, this is either a "Funny Aneurysm" Moment or Hilarious in Hindsight.
A "Meet the Press" sketch on the episode hosted by Senator John McCain (the genuine article, not a cast member impersonation) in 2002 had McCain denying that he would run for President in 2004. McCain was right; he didn't run in 2004. The 2008 election was a different story, and, as mentioned before, depending on your political leanings, the fact that McCain ran and lost is either an aneurysm moment or Hilarious in Hindsight.
Even the Jean Doumanian era isn't immune to the Funny Aneurysm Moment. At the end of the first episode (hosted by Elliot Gould), Gould introduces the cast again and tells the audience, "We're gonna be around forever!" Eleven episodes later, all but Eddie Murphy and Joe Piscopo were fired after the F-bomb debacle on the episode hosted by Charlene Tilton, and most of the cast members from that season haven't really been in the spotlight since then (with the possible exceptions of vastly-underused cast member at the time Gilbert Gottfried, Eddie Murphy [despite the career slump], and Gail Matthius, who did voice acting in a lot of 1980s and 1990s cartoons before becoming an improv and theater teacher).
Speaking of the Charlene Tilton episode, the whole "Who Shot C.R.?" running joke is a lot less funny, considering that Charles Rocket took his own life in 2005 (even worse is the fact that Charles Rocket in the sketch got shot in the neck and wore a bloodied bandage during the infamous "Goodnight" part; in Real Life, he slashed his throat with a pair of box cutters) and SNL would later have a cast member who was shot in cold blood (Phil Hartman).
An in-sketch example: "The Carter 'N Sons Barbecue" fake commercial from the Taylor Swift episode (season 35), which was supposedly filmed in 2002 and didn't air until 2009, which was when the H1N1 ("swine flu") virus was much-talked-about. The "commercial" was plastered with disclaimers stating that "swine fever" (an appetite for Carter 'N Sons brand barbecued pork) wasn't associated with the H1N1 virus (followed by a disclaimer reading that the management regrets naming their Sausage and Ribs Sampler platter "S.A.R.S").
Speaking of SNL and the swine flu, a lot of the second season jokes and sketches about the swine flu outbreak in 1976 ceased being dated when round two showed up in the late 2000s.
In the 1985-1986 season, there was an episode hosted by Pee-Wee Herman that had two (count 'em two) Aneurysm Moments:
The cold opening where Pee-Wee Herman performs a tightrope walk across the World Trade Center towers and falls, screaming the show's opening line. Thanks to the 9/11 attacks, whatever humor can be mined from this sketch has been tainted from tragedy (like everything else made before 2001 that shows New York City with the World Trade Center towers as part of the skyline).
Then, there was a sketch where Pee-Wee Herman is thrown in jail and meets the Pathological Liar, Tommy Flanagan (played by Jon Lovitz). Pee-Wee Herman (or rather, the actor who plays him [Paul Reubens]) would find himself on the wrong side of the law in the 1990s and early 2000s (both for sexual offenses). That Pee-Wee is screaming, "I'm innocent! I'm innocent!" adds to the cringe factor of rewatching this sketch.
The Christmas episode from season 28 (2002-2003 season): in the cold opening, Al Gore is worried when he can't find his wife, Tipper, then when he finds her, they kiss so long and so hard that it takes a taser for them to separate. It took eight years: on June 1, 2010, Al and Tipper announced their separation.
In the Colin Firth/Norah Jones episode from season 29, Darrell Hammond as Bill Clinton remarks that John Edwards is like a "boring version" of himself, stating, "This guy might have sex in the Oval Office, but he’d probably do it in the missionary position - with his wife." Thanks to the Rielle Hunter affair and the sex tape scandal, that line rings hollow.
A sketch on the Topher Grace episode from season 30 (2004-2005 season) called "The Not Incredible Adventures of the Down-And-Out Dollar" parodies the fact that the U.S. dollar had reached an all-time low by having a tiny dollar bill (Amy Poehler) being mocked by currencies from other countries, one of which is a Euro (played by episode host, Topher Grace), who brags that he's doing well in every country in the European Union. That would prove to be so very false five years later with news of several European countries suffering from economic meltdown (what's worse is that the Euro mentions that Greece was doing better than America economically in 2005, which isn't true now). In addition, economic trouble in the U.S. combined with a declining trust in government and the dollar means the moment hits home as well.
Back in 1982, there was an episode hosted by Drew Barrymore - fresh from ET The Extra Terrestrial and Firestarter, all smiles and curls, just seven years old (making Barrymore the youngest host SNL has ever had, beating out Jodie Foster, who was 14 when she hosted in 1976) - who finished her monologue by asking for a drink. "After all," she declared with a broad wink, "I am a Barrymore." Her family legacy of alcoholism and self-destructive behavior would catch up with her for real, and in a big (bad) way, not long after. Subverted in that there is a happy ending to all of this: Drew Barrymore managed to climb out of the same pit of drugs and despair as her ancestors did and has come back to host a few more times, now becoming SNL's most frequent female host (beating out Candice Bergen, who frequently hosted in the early days of the show) as of October 2009.
In the SNL Digital Short on the Gwyneth Paltrow/Cee-Lo Green episode, Andy Samberg has a wild, drunken night out with Pee-Wee Herman (the same one who hosted SNL in 1985 during its 11th season). During this night out, they break a chair over Anderson Cooper's head in the street (and Cooper comes back later in the short with a bandaged head, complaining that his blue eyes [which he considers one of America's national treasures] almost got destroyed). Less than three weeks after the sketch aired, Anderson Cooper really was brutalized in the streets during his coverage of Cairo's uprising.
A 1970s episode hosted by Steve Martin had a sketch called Jeopardy 1999. It was basically Jeopardy in a (then) futuristic setting. One of the answers was, "Comedian whose career fizzled when he left NBC's Saturday Night" The question: Who is Chevy Chase? While Chevy has currently found fame on the NBC sitcom Community, he did go through a career decline after leaving SNL, making that line eerily prophetic.
Lindsay Lohan's monologue during her 2005 hosting appearance included a visit from her "future self"note from 2007 played by Amy Poehler, warning her to stay away from her drinking, partying ways. She didn't end up marrying Tommy Lee and hosting a Cinemax show called Night Passions, but what did start happening not too soon after that made this monologue eerily prophetic as well.
Mr. Bill was a popular SNL sketch from the 1970s. While this didn't air on SNL itself, there was a spin off video "Mr. Bill's 20th Anniversary where he goes hang gliding off the World Trade Center, and is sucked into an airplane jet engine and one where he's duct taped to the space shuttle Columbia. Ouch!