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.
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