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Not Your Average Dick in a Box: Justin Timberlake’s 10 Best ‘Saturday Night Live’ Moments

justin timberlake, snl, saturday night live

Justin Timberlake will host Saturday Night Live for the fifth time tomorrow night (March 9), making The 20/20 Experience maestro the newest member of the ever-prestigious “Five-Timers Club.” Now, instead of miscasting himself as heir to Led Zeppelin’s epic-jams throne, the “Suit & Tie” singer can claim funnymen Bill Murray, Alec Baldwin, and Steve Martin as peers. To commemorate this rite of comedic passage, we’ve rounded up the 10 best things he’s ever done on the show.

Sketch: Opening Monologue (Britney Spears)
When: February 2, 2002
For Britney Spears’ second time doubling as SNL host and musical guest, the “Slave 4 U” starlet got a little opening monologue assistance from then-cast member Chris Kattan (remember Mango?) and then-boyfriend Justin Timberlake. This light-on-laughs clip works better as an early-aughts time capsule than a comedy piece — a reminder of a not-so innocent time when Britney’s virginity was still a matter of dispute and Timberlake coiffed himself in platinum-blond macaroni curls.

Sketch: “Target”
When: May 9, 2009
Timberlake repeatedly falls back on a simple catchphrase — “Claaaassic Peg” — for this skit, but the draw is seeing the “Mirrors” man, made up as an elderly woman in comfort slacks, wiggle and giggle as Kristen Wiig lays it on thick as the overeager Target lady.

Sketch: “Dick in a Box” (SNL Digital Short)
When: December 16, 2006
You knew this would be here. Carry on.

Sketch: “The Barry Gibb Talk Show”
When: December 16, 2006
Jimmy Fallon may take the lead here — he’s Barry effing Gibb, after all — but Timberlake makes a great straight man to the impression-ist and Late Night host. The Legend of Summer struggles not to break character, something he’d eventually do on “The Barry Gibb Talk Show” in 2009, but this falsetto-filled short makes good use of his pipes.

Sketch: “Single Ladies”
When: November 18, 2008
Beyoncé, Bobby Moynihan, Andy Samberg, and Timberlake in heels and black leotards. You can watch the whole thing here.

Sketch: “Weekend Update” (Seth Meyers)
When: March 7, 2009
Timberlake purposely did not bring sexy back for this “Weekend Update” cameo. Working off Andy Samberg’s pitch-perfect interpretation of comic strip crank Cathy, the FutureSex/LoveSounds king dons an unfortunate wool sweater and speaks in a nasally, common cold-infected tone to play Irving Hillman, Cathy’s nebbish beau. JT’s real-life boo, Jessica Biel, steals the show, though, when she struts in as animated va-va-voom vixen Jessica Rabbit. The creepy male gaze strikes again.

Sketch: “Motherlover” (SNL Digital Short)
When: May 9, 2009
The “Dick in a Box” douche duo return for this R-rated ode to mom swappin’. Our totally inappropriate thumbs-up to whomever cast IRL MILFs Susan Sarandon and Patricia Clarkson.

Sketch: “3-Way (The Golden Rule)” (SNL Digital Short)
When: May 21, 2011
Okay, this bit really should be past its expiration date by now, but somehow it still works. Maybe it’s the Lady Gaga cameo, or the continuity from the “Motherlover” short, or the sleazeball bomber jackets. The syrupy chorus certainly helps.

Sketch: “Liquorville”
When: May 21, 2011
Ever wonder what it’d be like if Justin covered Rihanna’s “Rude Boy” while dressed as a cartoon 40-ounce bottle? Here’s your answer.

Sketch: “Weekend Update” (Seth Meyers)
When: November 15, 2008
And for his final trick, Justin Timberlake will squeeze an entire episode of SNL into a three-minute “Weekend Update” guest appearance. The pricey merchandise pusher narrates the sketch show’s opening credits sequence; speeds through a hypothetical opening monologue; skips over a quick commercial parody; unveils a spotty Vincent Price imitation; pitches a “Dick in the Thanksgiving Turkey” short; sings a brief acapella sample of “My Love”; gives a shout-out to Kristen Wiig’s Target lady; distills “The Barry Gibb Talk Show” to its purest essence; and signs off, waving to the camera. At this point, he doesn’t even need the cast.