Justin Timberlake’s 10 Greatest ‘Saturday Night Live’ Moments

Who knew Justin Timberlake could be one of the funniest guys in showbiz? No NSYNC fan certainly did, and there was no real indication of it when he was putting out his first broody solo singles after his break-up with Britney Spears. Leave it to Saturday Night Live to reveal what a true comedic genius the multi-hyphenate talent really is.

Over the last 12 years, since he first stepped onto the Studio 8H stage as host in 2003, Timberlake’s become a staple on the sketch show. In fact, his contributions to SNL history have been so memorable that the series is dedicating six hours tonight to reairing his episodes on VH1 Classic as part of the “SNL Rewind: 2015-1975 Mega Marathon” happening right now. But before you change the channel and spend of the rest of your day bingewatching JT, here’s the cliff notes version, i.e. his 10 greatest moments on Saturday Night Live.

He Pulls Out His “Dick in a Box” Digital Short (Season 32, Episode 9)

Is “Dick in a Box” a Millennial’s “The Christmas Song?” “Chestnuts roasting on an open fire” does sound pretty hilarious out of context. The new holiday carol should make it’s way to every station come December 1st. Either way, it’s already made history: the short, by Timberlake and The Lonely Island (Andy Samberg, Jorma Taccone, and Akiva Schaffer), won a Creative Arts Emmy for Outstanding Original Music and Lyrics in 2007.

He Joins the BeeGees on “The Barry Gibb Talk Show” (Season 32, Episode 9)

Alongside his late night buddy, Jimmy Fallon, Timberlake got to play Robin Gibb of the Bee Gees on “The Barry Gibb Talk Show,” where they spoke seriously about politics in falsetto. Hairy chest and gold chains were not optional. Thanks to the popularity of this sketch, now fans know that when Jimmy Fallon hosts, Justin won’t be far away.

He Recreates “Single Ladies” (Season 34, Episode 8)

It’s rare, it’s powerful, and it’s a sight to behold. No, not a solar eclipse. We’re talking about when two supernova stars collide, Beyoncé and Justin Timberlake. It’d be nice if they performed a duet, of course. But Justin playing a backup dancer for the mega star’s “Single Ladies,” alongside Bobby Moynihan, Andy Samberg, and Paul Rudd, is a lot nicer, especially in his leotard and heels.

He Pays the Target Lady a Visit as Peg (Season 34, Episode 21)

The only thing that could be funnier than Kristen Wiig as the Target Lady is Timberlake dressed up as a grandma named Peg. While the Target Lady has a passion for Target products, Peg has a passion for saying, “Classic Peg,” after all her stories. Basically, their friendship was made in retail heaven.

He Serenades Susan Sarandon With “Motherlover” (Season 34, Episode 21)

In 2009, the “Dick in the Box” singers returned with their silky smooth R&B hit, “Motherlover,” written by The Lonely Island. It’s not just about making love to women. It’s a song about friendship. More specifically, friends that are so close that they actually encourage one another to make love to each other’s moms (here, played by Susan Sarandon and Patricia Clarkson). It’s a bro code that not many abide by.

He Invites You to Liquorville (Season 36, Episode 22)
Very few hosts get to have recurring characters. Timberlake certainly created one, officially named the “Dancing Mascot,” when he donned a life-size beer costume and told everyone to “Bring it on down to Liquorville…” while transforming pop songs into commercial jingles for the company he’s working for.

He Reminds You of The Golden Rule With “3-Way” (Season 36, Episode 22)

Two years after Samberg and Timberlake made love to each other’s moms, they had the “Dick in a Box” singers climb yet another mountain of friendship: being in a three-way with one girl. The golden rule? It’s not gay if it’s in a threeway.

He Disses Kanye West During His Performance of “Suit and Tie” (Season 38, Episode 16)
After Kanye West took a dig at Timberlake’s song “Suit and Tie,” saying during a concert, “I got love for Hov, but I ain’t f**king with that ’Suit & Tie,” the singer retaliated. Timberlake appeared on SNL and altered some of lyrics of his single to express, “My hit’s so sick got rappers acting dramatic.” Not only was JT funny, but he also didn’t take any of Kanye’s lip.

He’s Inducted Into the Five-Timer Club (Season 38, Episode 16)

The Five-Timer Club is reserved for the very few who have hosted SNL five times, making it easily the most exclusive club in New York City. It was impressive to see Timberlake join the club so quickly (his first time was in 2003, and his fifth was in 2013), as other five-timers came out to celebrate with him, including Steve Martin, Paul Simon, Chevy Chase, Alec Baldwin, Tom Hanks, and Candice Bergen.

He Plays Celebrity Family Feud as Jimmy Fallon (Season 39, Episode 10)

If it isn’t obvious already, JT isn’t one of those celebrities who takes himself too seriously. He wouldn’t start a website called Goop, and he wouldn’t publish a book on how to make marriage work. He’s down to earth, but then again, you have to be when your claim to fame was synchronized dancing with four other full grown men. In this sketch, he impersonates Jimmy Fallon, as Jimmy, the host of the episode, stands across from him parodying Jim Parsons.

Watch Justin Timberlake take on musical guest duties for his BFF Jimmy Fallon:

[Photo Credit: NBC/Getty Images]

Tara Aquino is an entertainment writer based out of L.A. She likes people, places, and things.