On Saturday night, Justin Timberlake will be inducted into the Five-Timers Club — an elite squad of the few funny people who have hosted Saturday Night Live five times. (Technically, this is actually Timberlake’s sixth official appearance on the show; when Joshua Jackson hosted in 2000, ‘N Sync served as musical guest and also performed in a few sketches.)
The multitalented musician certainly deserves a spot alongside Christopher Walken and Tom Hanks. As he’s proved over and over again since his first hosting stint ten (!) years ago, Timberlake’s pretty much the best modern SNL host this side of Alec Baldwin — which means that narrowing down his best Saturday Night Live moments is about as tough as getting the “Barry Gibb Talk Show” theme song out of your head once it’s stuck there. (Er, sorry in advance.) Still, we managed to sift through an embarrassment of JT SNL clips somehow — and though many of them were gems, these 10 stand out.
10. “Barry Gibb Talk Show” (2006)
As the name implies, these sketches are more of a showcase for Jimmy Fallon (as short-fused Bee Gee/political talk show host Barry Gibb) than Timberlake (as his mostly mute brother Robin). But the conceit wouldn’t work without JT”s pitch-perfect harmonizing, or the way he shakes his groove thang while singing about chest hair and crazy cool medallions. The sketch’s first appearance in 2003 is pretty good, but its third appearance on SNL‘s Christmas show in 2006 is even better — largely because in this one, Timberlake has a little more to do.
9. “At Home with Beyoncé and Jay-Z” (2012)
This bit from last year’s Maya Rudolph-hosted episode features plenty of excellent celebrity impressions, including Jay Pharoah’s Jay-Z, Fred Armisen’s Prince, Nasim Pedred’s Nicki Minaj, and Kristen Wiig’s Taylor Swift. But its best surprise is Timberlake’s cameo as Bon Iver’s Justin Vernon, who hits Bey and Jay’s house after wandering barefoot through the woods of Wisconsin and fashioning a guitar out of a canoe. White Butler’s not the only one who will be into this:
NEXT: An American tale, starring Cornelius Timberlake
8. “Amusement Park Ride” (2011)
The creepy, animatronic Merryville Brothers first appeared when Jim Carrey hosted SNL in January 2011. Four months later, Timberlake proved that he could play a robot just as convincingly as Carrey — leading to a sketch that’s both very funny and technically impressive.
7. “Immigrant Tale” (2009)
Recurring sketches are SNL‘s bread and butter, but often its one-offs are the funniest bits of all. Take, for example, JT’s turn as Cornelius Timberlake — an Irish immigrant who imagines an extravagant life for his great-great-grandson, including a career as a musician famous for his falsetto (“It’s a perfectly normal way to sing!”) and his relationships with beautiful women (“He’ll date a popular female singer. Publicly, they claim to be virgins but, privately, he hit it”).
NEXT: “Pushin’ that place that you came out as a baby…”
6. “Plasticville” (2009)
Every time Timberlake hosts SNL, he dons a goofy foam costume — a beer bottle, a breast implant, a Cup O’ Soup — to play a buoyant store mascot who sings doctored versions of popular songs. Bring it on down (or give it on up) to Omeletteville, Homelessville, Plasticville, or Liquorville; they’re all equally good. “Plasticville,” however, is the only member of the series we could find easily and legally online.
5. “Motherlover” (2009)
After serving five months in prison for indecent exposure, the “Dick in a Box” boys realize that they’ve each forgotten Mother’s Day. Then they have their second-best idea ever: Why not switch places and give each of their moms (played brilliantly by Patricia Clarkson and Susan Sarandon) a gift she’ll never forget? You can watch the uncensored video via Funny or Die, but the bleeped version is actually even more cool and thoughtful:
NEXT: Justin’s not gonna sing. Really. [enter pork pie hat]
4. “Monologue” (2011)
In the days of Friends with Benefits and In Time, Timberlake was still deep into his musical hiatus — which was why Lady Gaga served as musical guest the last time he hosted the show. There was just one way for Timberlake to explain that he wasn’t planning to sing: by doing just that, in a tuneful, self-referential tour de force that wound up winning him a Best Original Song Emmy (shared with co-writers Katreese Barnes, John Mulaney, and Seth Meyers). He also nabbed a Guest Actor statuette that year for his work on this episode as a whole.
3. “What’s That Name?” (2011)
SNL does a lot of game show parodies — too many, in fact — and most of them get old immediately after their central joke is exposed. But “What’s That Name?” has a clever conceit that builds and builds until it reaches the greatest ‘N Sync joke ever told. Saying any more would ruin it for first-time watchers — so just push “play”:
NEXT: One, cut a hole in the box…
2. Weekend Update (2008)
Back in ’08, Timberlake was on board to host SNL‘s Thanksgiving episode — then had to back out at the last minute. Thankfully, he made up for canceling with a surprise appearance on the show the week before he was scheduled to host. Timberlake stopped by the Weekend Update desk to break the bad news — then gave a detailed play-by-play of what would have happened if he could have hosted after all. In just three minutes, Timberlake generated more laughs than some hosts manage in an entire night. (His Don Pardo impression ain’t half bad either.) And as icing on the cake, he did the “Single Ladies” dance with musical guest Beyoncé later that night.
1. “Dick in a Box” (2006)
The Digital Short that’s largely responsible for Timberlake’s stellar hosting reputation is still as funny as you remember — and maybe even funnier, because that annoying guy in your office probably stopped making references to it years ago. It’s JT’s finest SNL moment — in a box!
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