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Justin Timberlake Shows Off His Impeccable Singing and Comedic Chops in These SNL Sketches

The "Cry Me a River" singer has had SNL audiences laughing over the years, even making it into the prestigious Five Timers Club.

By Ethan Sacks
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Over the last 25 years, pop superstar Justin Timberlake has brought sexy back to Studio 8H multiple times.

How to Watch

Watch Saturday Night Live Saturdays at 11:30/10:30c on NBC and Peacock, streaming next day on Peacock.

A member of Saturday Night Live's prestigious Five-Timers Club that includes the likes of Tom Hanks and Alec Baldwin, Timberlake has returned regularly to the show as a Host, as a Musical Guest, and sometimes as both, and in the process starred in some of the most iconic SNL sketches of recent memory. The 43-year-old’s connection to SNL has paralleled his career trajectory from teenage boy-band member to multi-platinum solo artist to movie star.  

Timberlake showed a flair for the spotlight from a young age, joining the cast of the All-New Mickey Mouse Club for the 1993-94 season as part of a group of future superstars that included Britney Spears, Christina Aguilera, Ryan Gosling, and J.C. Chasez.

After the show’s cancellation, Timberlake would team with Chasez and three other singers – Lance Bass, Joey Fatone, and Chris Kirkpatrick – to form the boy band, NSYNC. At the time Timberlake was just 14, but within a few short years he would become the most popular member of one of the most popular music groups on Earth.

RELATED: NBC Is Airing SNL's Very First Episode Ahead of Its Anniversary Special: How to Watch

When Was Justin Timberlake’s First SNL Appearance?

Timberlake would make his SNL debut as a musical guest on March 11, 2000, with NSYNC. The band was at the peak of its popularity at the time, performing in support of the album, "No Strings Attached," which has sold more than 14 million copies worldwide in large part fueled by the single, "Bye Bye Bye," which is still worming its way through our collective ears all these years later.  

But Timberlake was just getting started.

Three years later, on October 11, 2003, he would return for his first double-duty stint as Host and Musical Guest. He was 22 at the time, just a few months into a solo career following the release of his debut album, Justified. That SNL episode would prove that Timberlake was more than a pretty face with silky pipes, showcasing his comedic chops. The episode would also mark the first time he portrayed Bee Gees member Robin Gibbs alongside Jimmy Fallon as the titular frontman in "The Barry Gibbs Talk Show."

Justin Timberlake and Jimmy Fallon singing on Saturday Night Live Season 36, Episode 22.

How many times has Justin Timberlake been on SNL?

Timberlake has made a total of 16 appearances on the show in various capacities.

As Musical Guest:

  • March 11, 2000 (with NSYNC)
  • December 21, 2013 (solo)
  • January 24, 2024 (solo)

As Host/Musical Guest:

  • October 11, 2003
  • December 16, 2006
  • March 9, 2013

As Host:

  • May 9, 2009
  • May 21, 2011

He's also made eight other cameos. 

On March 9, 2013, the 10-time Grammy winner was enshrined in the prestigious “Five Timers Club” of hosts; and was feted in a memorable sketch by fellow members including Steve Martin, Candice Bergen, and Alec Baldwin.

In addition, Timberlake's time on SNL has earned him four Emmy Awards.

Noel Wells, Aidy Bryant, Justin Timberlake, Jimmy Fallon performing during Saturday Night Live Season 39, Episode 10.

RELATED: Elvis Costello Explains Why He Switched to Singing "Radio, Radio" on SNL in 1977

Some of Justin Timberlake's most memorable SNL sketches

"The Barry Gibbs Talk Show" (2003-2024)

SNL + Jimmy Fallon + Justin Timberlake + Bee Gees = Comedy Gold.

Timberlake teamed up with Fallon for the first time to portray brothers Robin and Barry Gibbs on October 1, 2003. The premise was as simple as it was ludicrous: what would it be like if the Bee Gees alums hosted a political talk show? Fallon’s fiery-tempered, martial-arts-kicking Barry was the centerpiece of the gag as he threatened a succession of notable political figures, but Timberlake’s Robin wouldn't be overshadowed. His repeated answers of “No, I don’t,” to every question and seamless, random harmonizing in falsetto was an instant hit. The sketch proved so popular that the pair would reprise those roles six more times between 2003 and 2024. The real Barry Gibbs even got in on the fun with a surprise cameo in one of the sketches in 2013. 

The Barry Gibb Talk Show

"D*** in a Box" (2006) 

This 2006 SNL Digital Short from the Lonely Island crew paired Andy Samberg and Timberlake as a '90s-style pop duo delivering a tune that somehow delivered sincerity and smarminess with equal measure. The result was a viral sensation about two lovers gifting their sweethearts with … well, you get the idea from the title. "We're kind of close to the same age, so we kind of grew up with that kind of '90s R&B group sound when we were kids, so we had this idea about those groups and how to do a joke about guys who were still stuck in that era," Timberlake recounted in the book, Live From New York.

SNL Digital Short: D*** in a Box

"Single Ladies" (2008)

This sketch is notable because Timberlake was neither hosting, nor serving as Musical Guest for the November 18, 2008 episode when he, Samberg, and Bobby Moynihan donned leotards and high heels to get down as backup dancers for Beyoncé – but it certainly counts among his more memorable. In fact, Timberlake played a pivotal role in convincing Beyoncé it was a good idea. 

As Timberlake recounts in Ladies & Gentlemen... 50 Years of SNL MusicQuestlove and Oz Rodriguez's documentary, his involvement started with a text from Samberg: “He said Bobby Moynihan has this great idea for a sketch about you, me, and him being Beyoncé’s background dancers that never made the cut. I was like ‘Full leotard’? And he’s like, ‘Yeah.’ I was like, ‘This is too funny. We have to do this.’”

But then they had to convince an apparently skeptical Beyoncé.

“She was very polite about it, but she was very hesitant. And when I say hesitant, I mean like, she was not having it,” he recalled. “I’m like: Does she know how funny this is gonna be? How beloved this whole moment will be?”

Fortunately, after Timberlake donned the leotard and heels to show her just how hilarious the look would be, she was on board.

Justin Timberlake, Paul Rudd and Beyonce dance on Saturday Night Live Season 34 Episode 8

"Motherlover" (2009)

Those "D*** in a Box" singers were such a hit that Timberlake, Samberg and the Lonely Island crew brought back the duo for several additional SNL Digital Shorts. Perhaps none of their ballads brought more power – star power, that is – than "Motherlover." The ode to sleeping with your best friend’s mother featured guest appearances by Academy Award winner Susan Sarandon and acclaimed actress Patricia Clarkson, who played the pop duo's respective mothers and lovers. The song featured the immortal lyric, "I'll push in that lady, where you came out as a baby."

SNL Digital Short: Motherlover

"Immigrant Tale" (2009) 

The premise of this classic sketch involved a boat full of immigrants coming from Ireland and arriving at Ellis Island in 1883 in search of a better life. Among them: one Cornelius Timberlake, the great-great-grandfather of the future SNL host. As he dreams of the opportunities that his descendant will enjoy in this New World, his predictions are surprisingly on the nose.

“I actually dream of the day when my great-great-grandson will bring Sexy back,” says Cornelius.

“Bring Sexy Back? What does that mean?” asks a fellow passenger played by Bobby Moynihan.

“It will be gone, and he will bring it back,” answers Timberlake.  

Immigrant Tale

"Opening Monologue" (2011)

Justin Timberlake did what he does best for his opening monologue on May 21, 2011: combining pitch-perfect comedic delivery with pitch-perfect crooning. It all started with Timberlake’s vow to reject executive producer Lorne Michael’s request that he sing on that night's show. Timberlake protested because he was not there as a musical guest. Instead, he decided to explain his position to Michaels – through song. The result, "I'm Not Going to Sing Tonight," was a jaunty jazz tune, with lyrics cowritten by Timberlake, Seth Myers, and John Mulaney, and music by Katreese Barnes, which ended on the ultimate high note: an Emmy Award for Outstanding Original Music and Lyrics.

Justin Timberlake Monologue

"3-Way (The Golden Rule)" (2011)

Timberlake and Samberg (AND Sarandon and Clarkson) returned for yet another SNL Digital Short and another chance to croon an inappropriate tune, this time about sharing an intimate experience with your lady … and with your best friend. Lady Gaga lent her vocals and her presence as the woman in the middle of that strange love triangle. What was the titular Golden Rule? That “it’s okay, when it’s in a 3-way.”

Digital Short: 3-Way (The Golden Rule)

"What’s My Name" (2011) 

In this 2011 installment of the recurring sketch about the titular fictional game show in which contestants have to identify the names of people in pop culture or in their own lives, Timberlake delivered an impression of … himself.  As the host, played by Bill Hader, summoned forth a succession of subjects – including a woman who claims to have had a one-night stand with the singer two weeks earlier – Timberlake awkwardly fails to identify any of them. Meanwhile, fellow contestant Lady Gaga remembered everyone's name in the crew and audience.

What's That Name?

"It’s a Date" (2013)

On another mock game show hosted by Bill Hader, Vanessa Bayer must choose between three bachelors for a date. Actually, it turns out to be five as poor Contestant A (Bobby Moynihan) has to compete against both the legendary "Wild and Crazy Guys" (with Dan Aykroyd and Steve Martin reprising their roles from early days of SNL) and the "D*** in a Box" singers. Timberlake and Samberg reprise their roles as the sex-starved crooners and that makes everybody watching a winner ... well, except that beleaguered Contestant A.

"Bring it on Down to Veganville" (2013)

Nobody could pull off giant cartoonish gloves and boots with more fashionable flare than Timberlake, who played a Tofu mascot from the Veganville restaurant engaged in a war for attention with an employee of the rival Sausage Depot. The singing and rapping slab of Tofu performs a medley of popular song parodies with vegan themes, including Veg Out to the tune of Chic’s Le Freak. Spoiler: By the end, his recipe for attention is so good that he even has his rival dancing to his tune. Timberlake performed variations on the same premise seven times over the years, first with "Omeletteville" in 2003. 

Veganville

About SNL50: The Anniversary Special

The three-hour SNL 50th anniversary special aired February 2025 on NBC and can now be streamed on Peacock.  Aptly titled SNL50: The Anniversary Special, it celebrates a half-century worth of sketches, cast members, Hosts, and other collaborators. Watch it here. 

You also can watch Peacock's four-part docuseries, SNL50: Beyond Saturday Night, as well as Ladies & Gentlemen ... 50 Years of SNL Music, a documentary about SNL's Musical Guests that's co-directed by Questlove and Oz Rodriguez, on Peacock, too. The SNL50 concert special is also available on Peacock. 

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