The Best And Worst SNL Skits Of All Time

Saturday Night Live has aired thousands of sketches during its 40-plus years on the air. It's hard work turning out 90 minutes of live, original comedy, and the quality is naturally going to vary. Some of those bits have stood the test of time and become classics, while others have become memorable because they were so ill-conceived. (There's also the matter of taste—one person's all-time great is another's trash.) In no particular order, here are 12 of the very best sketches to ever air on SNL...along with 12 of the very worst.

In the current pop culture landscape, Jeffrey Tambor has won two Emmys for his thoughtful and sensitive portrayal of a transgender woman on Transparent. In the early '90s, SNL featured a recurring bit with Julia Sweeney as a gender-ambiguous character with the gender-ambiguous name of Pat. The joke was that observers couldn't tell if Pat was a woman or a woman, and Pat would obscure things further by dating a gender-ambiguous person named Chris. The character was annoying and obnoxious then—Pat constantly simpered, wined, and winced—but is problematic if not offensive now.

January Jones excels at playing unapproachable women—Emma Frost in the X-Men movies, or Betty Draper on Mad Men, for example. In this sketch, she's another distant and mysterious character: Grace Kelly during the making of the 1953 classic movie Rear Window. While Jones would later show a real gift for comedy on The Last Man on Earth, she comes off in this sketch as awkward and strange—probably because the premise is entirely based around her inability to stop farting.

Obviously, Kristen Wiig is one of all-time SNL greats: adept at celebrity impressions, physical comedy, silly voices, and great original characters. And then there's Gilly, a recurring character so obnoxious and difficult to enjoy that she feels like a parody of recurring characters. Dressed in a fright wig, Wiig plays a little kid who acts innocent even though she's obviously guilty of savage pranks. The greatest prank ever pulled on the audience, however, is this character's stubborn refusal to go away.

This may not be one of the worst written sketches in SNL history, but it's among the worst executed. Former cast member and host Chris Rock stars opposite the fantastic Leslie Jones as a long-married bickering couple getting ready to go out. The sketch isn't particularly funny; it's loaded with so much emotional nuance, story, and poignancy that it feels more like a short play. When it aired, the scene was besieged with so many technical difficulties and messed-up lines that none of the actors could pull it out of a tailspin.

SNL can, should, and does try to skewer people from all walks of life, but there's a fine line between social commentary and pointless cruelty. In this sketch that aired during SNL's strike-shortened misbegotten 1980-'81 season, a bunch of angry guys with thick country-fried accents can't wait to go out hunting "Commies"—America's number one enemy at the time. Charles Rocket's character is so repugnant that he actually says the N-word on the air. The studio audience responded with utter silence.

See, what they did here is take "Jack the Ripper" and changed it to "Jack the Stripper," because it rhymes. That's pretty much the sum total of the joke. A guy in grimy, Victorian-era London flashes people rather than murder them, and investigators are pretty sure it's a member of the royal family because the culprit wears a luxurious robe.

What if the Three Wise Men were the Three Wise...Guys? That little bit of wordplay substitution led to this Christmas bit, in which the trio on their way to deliver presents to the Baby Jesus were instead members of the Mafia. The sketch features three guest stars—Robert De Niro, Sylvester Stallone, and John Goodman—talking like movie mobsters. Or at least, that's probably what they're doing. They're so difficult to understand (especially Stallone) that it's hard to tell exactly what's happening.

Eddie Murphy was SNL's breakout star in the early '80s, but the show's other big laugh-getter was Joe Piscopo, a solid, funny performer who could do a great Frank Sinatra. His recurring characters, however, needed some work. In "The Whiners," he and Robin Duke played Doug and Wendy Whiner, a couple who, coincidentally whined all the time. The joke is that they annoy everybody, but if the sketch also annoys the audience, what's the point?

Some of the most common criticism SNL receives has to do with its reliance on recurring characters and catchphrases. Here's one example. Rob Schneider plays an office worker—"the Richmeister"—who sits by the copy machine and riffs on co-workers' names, then says "makin' copies." That's it. What might have been a clever sketch for two minutes one time gets old quite fast when one office employee after another makes copies...and then SNL repeats the whole thing week after week.

Sharon Stone shot to fame with Basic Instinct, a sexually charged psychological thriller in which she bared a lot more than her acting chops. SNL seemed more interested in her physical attributes than talents, however, and cast her in this sketch as a woman airport security finds so attractive that they keep making her remove articles of clothing to "make sure" she isn't "smuggling anything." In other words, Sharon Stone is forced to strip—and it's more sexist than it is sexy.

The very public and messy divorce of Prince Charles and Princess Diana was one of the major news stories of 1992, dredging up embarrassing information about both parties—including a recording that surfaced of Charles on the phone with his then-mistress (now wife) Camilla Parker-Bowles expressing his desire to be transformed into a feminine hygiene product so he could be with her always. This SNL sketch takes the concept to its logical and tasteless end—Prince Charles (Dana Carvey) announces his abdication from the line of royal succession so as to get together with some scientists and literally make that wish come true.

Athlete guest hosts almost always strike out on SNL. They're generally stiff, dull, and not funny, so the show has to rely on tired tricks to get through those episodes—which usually includes dressing the manly jock in women's clothes. When New York Yankees great Derek Jeter hosted, he played the wife of a Yankee hanging out with other ballplayers' wives in the Yankee Stadium grandstands. The entire joke here is that Derek Jeter is wearing a dress, and it's funny for about as long as you'd think.