Top 10 Funny Justin Timberlake SNL Moments
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VOICE OVER: EB
Script written by Jason Porter
Justin Timberlake has really stepped up his game in terms of his comedic performances in the last few years. He's a staple on SNL and always kills it. We've included some of his best SNL moments like Dick in a box, his classic Peg Impression, his Irving Hillman impression, appearing with Britney Spears in her monologue, motherlover, celebrity family feud, veganville and more!
Justin Timberlake has really stepped up his game in terms of his comedic performances in the last few years. He's a staple on SNL and always kills it. We've included some of his best SNL moments like Dick in a box, his classic Peg Impression, his Irving Hillman impression, appearing with Britney Spears in her monologue, motherlover, celebrity family feud, veganville and more!
#10: His Irving Hillman Impression
The daily newspaper comic “Cathy” is known for two things: its eponymous main character, and its unfortunate longevity. Once beloved, “Cathy” was long past its expiration date when it was finally canceled in 2010. In this classic Weekend Update sketch, Justin appears opposite Andy Samberg's Cathy as her beau, Irving Hillman, who professes a somewhat unhealthy attraction to Cathy's endless complaining and willful frumpiness. In the end, though, fellow cartoon woman Jessica Rabbit – played by Jessica Biel – comes along and steals Irving away. JT's gleeful willingness to lean into Irving's weird body language and inappropriate bedroom eyes is what really sells the bit.
#9: Target Lady - "Classic Peg"
Who could possibly be friends with Kristen Wiig's loud, self-absorbed, overly chipper Target Lady? Peg, that's who! Justin Timberlake's equally self-absorbed, gray-haired woman in a neck brace makes the perfect foil for Wiig as the two irritate and confuse customers while discussing their strange personal lives. Peg's bizarre and improbable stories fly fast and thick, always ending with a self-congratulatory “classic Peg!” Combined with “SNL”’s trademark peppering of gross-out humor – this time in the form of a body waxing appointment and a pair of fuzzy pink handcuffs – the Target Lady and Peg combination brought this sketch to new heights.
#8: Britney Spears' Monologue Appearance
Way back in 2002, when JT was dating fellow superstar Britney Spears, he made a surprise appearance on stage with her during her opening monologue as “SNL”’s host of the week. In the routine, Chris Kattan enters before Britney, impersonating her and claiming he's no longer a virgin since last night. The pop princess eventually calls Justin out to clear things up, and he tells Britney that he really had a good time the night before. When Britney responds that it was Kattan and not her, JT turns to the impersonator and…well, just watch. The idea that it's happened before is what makes the joke so funny.
#7: Bon Iver Impression
When Jay-Z and Beyoncé had their first child, Blue Ivy, “SNL” used the opportunity to showcase all of their best pop star impressions in a sketch where celebrities come to pay their respects to the newborn. Justin Timberlake steals the show as the royal family's final guest, Bon Iver, complete with a tweed jacket and unfortunate comb-over. He offers to sing a song he wrote for the baby, but Maya Rudolph's Beyoncé responds that they were about to put her to sleep. As Bon Iver starts singing a quiet song that eventually devolves into unintelligible garbage, he ultimately puts himself to sleep instead.
#6: Motherlover
Justin Timberlake's track record as a collaborator with The Lonely Island is just about perfect. In each case, he appears alongside Andy Samberg as the two play sleazy womanizers dressed in awful early-90s outfits. The duo backs each other up with increasingly inappropriate lyrics about their sexual fantasies. In the case of “Motherlover,” they sing about the possibility of having sex with each others' mothers – played by Susan Sarandon and Patricia Clarkson – as an impromptu Mother's Day present. Even more so than its follow-up song, “3-Way (The Golden Rule),” “Motherlover” exemplifies the hilarious gag of two gross dudes enabling and encouraging each other’s ideas far past the point of sanity.
#5: Celebrity Family Feud
This regular sketch is always funny, but the episode featuring JT and his real-life friend Jimmy Fallon takes the cake. Fallon plays “Big Bang Theory” star Jim Parsons – who remains in character as Sheldon – while Timberlake plays the part of “The Tonight Show” host himself. What makes the bit so memorable is JT's spot-on impression of Fallon, complete with kinetic hand gestures and facial expressions – and the way that the real Jimmy Fallon completely loses it. The brief shot of him doubled over in silent laughter behind his podium is enough to make anybody giggle.
#4: “Veganville” & More
Sometimes, repetition only makes things funnier. Our favorite former NSYNC star is well aware of this, and has made several appearances on “SNL” over the years to perform essentially the same bit, which somehow gets funnier every single time. In the “ville” skits, a local business owner tries to advertise some kind of product for sale, but gets upstaged by the “SexyBack” singer, who appears in a ridiculous costume, dancing and singing about another business that offers the same product. Whether it's “Omeletteville,” “Wrappinville,” or “Veganville” - with Timberlake dressed up as a giant block of tofu – he always sells us on the product and his goofy performance alike.
#3: The Barry Gibb Talk Show
This recurring sketch casts Jimmy Fallon as a nervous, violent version of Bee Gees member Barry Gibb, and Justin Timberlake as his meek brother, Robin. From Barry's bizarre singsong inflection and explosive temper, to Robin's lack of an opinion on just about everything, it's a routine that plays to the duo's strengths. Robin chiming in to sing harmony on Barry's vicious threats to his guests is our favorite part, but all of it works, which is probably why these best buds have come back to it so often over the past 15 years.
#2: Single Ladies Dancers
Take Beyoncé – as herself – dealing with Paul Rudd as a difficult music video director for her iconic megahit “Single Ladies,” add male backup dancers played by Justin Timberlake, Bobby Moynihan, and Andy Samberg, and you get this instant classic. The humor here comes from the dance visuals, which start out fluid and synchronized, but then go predictably haywire. As an accomplished dancer himself, JT's movements are especially sharp, and he helps to make the whole thing one of the strangest and funniest interpretations of the song to date. We've also got to hand it to Beyoncé for managing to keep a straight face the entire time.
#1: Dick in a Box
What more can be said about this instant classic? The result of JT's first and most famous Lonely Island collaboration, this icky R&B jam about a very special Christmas present went viral in a huge way. From the cornball outfits to the oily vocals, this is the music video that spawned two direct sequels and a thousand Halloween costumes. The breakdown of the steps involved in packaging and presenting the unusual gift perfectly mimics the step-by-step lyrics of 90s pop jams like Brian McKnight's “Back at One,” and the facial expressions of Timberlake, Andy Sandberg, and their ladies (Maya Rudolph and Kristen Wiig) put it all over-the-top.
