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Justin Timberlake may be a Grammy award-winning pop star. But through his Saturday Night Live appearances, he’s proven he has some serious comedic chops too. The singer/actor picked up four Emmy Awards for his work on the show — two for Outstanding Guest Actor in a Comedy Series and two for Outstanding Original Music and Lyrics.

 It’s been a while since he’s hosted. So, here’s a look back at some of Timerblake’s funniest SNL moments.

Justin Timberlake, Jimmy Fallon on 'Saturday Night Live'
Justin Timberlake, Jimmy Fallon on ‘Saturday Night Live’ | Dana Edelson/NBCU Photo Bank/NBCUniversal via Getty Images

‘Bring It on Down to Wrappinville’  — ‘SNL’ Season 39

Timberlake and his buddy Jimmy Fallon have a recurring sketch on SNL where they dress up as objects and try to get customers into their stores. In the season 39 bit, “Bring It on Down to Wrappinville,” Timberlake and Fallon are rapping Christmas wrapping store reps. 

‘D*** in a Box’ — Season 32

A throwback to the sexy ballads of the 1990s, Timberlake teamed up with SNL co-star Andy Samberg to make the digital short, D*** in a Box.”  The duo plays a wannabe R&B duo who swoon over their girlfriends (played by Kristen Wiig and  Maya Rudolph) with their “junk” wrapped in holiday boxes. The song earned Timberlake a Creative Arts Emmy for Outstanding Music & Lyrics in 2007. 

‘The Barry Gibb Talk Show’ — ‘SNL’ Season 29 

Another one of Timberlake and Fallon’s recurring sketches is “The Barry Gibbs Talk Show.” The duo first appeared as the Bee Gees singer Barry Gibb and his brother Robin on season 29. They interview and berate their guests in the sketch, all while maintaining that high-pitched Bee Gees sound.

‘Motherlover’ — ‘SNL’ Season 34

Timberlake and Samberg reprised their R&B singer personas for “Motherlover” — a song with which they honor each other’s mothers — Susan Sarandon and Patricia Clarkson — by sleeping with them. 

‘The Merryville Brothers: Love Tunnel’ — Season 36 

Timberlake and SNL stars, Bill Hader and Taran Killam are an animatronic barbershop trio in the season 36 sketch, “The Merryville Brothers: Love Tunnel.” When an unwitting couple (Jason Sudeikis and Nasim Pedrad) rides through a carnival’s love tunnel, they encounter the musical group and find them charming at first. But when the ride gets stuck, the robots start making creepy advances.

‘3-Way: The Golden Rule’ — ‘SNL’ Season 36

Timberlake and Samberg’s smooth R&B duo teams up with Lady Gaga for the digital short,  “3-Way.” In the song, the pair say goodbye to their moms and venture out to visit Lady Gaga. When she suggests they all sleep together, the duo sings, “It’s OK when it’s in a three-way.”


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