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NBC Insider The Tonight Show Starring Jimmy Fallon

Justin Timberlake and Jimmy Fallon's Best Late Night Moments

The pop star's onscreen chemistry with Tonight Show Host Jimmy Fallon has had us — and the two longtime friends — laughing for over 20 years.

By Samantha Vincenty

Justin Timberlake and Jimmy Fallon's longtime friendship has been a creatively fruitful one. Over the years the two have teamed up for dozens of sketches, interviews, and musical performances on shows including Saturday Night Live, Late Night with Jimmy Fallon and, of course, The Tonight Show Starring Jimmy Fallon

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Timberlake and Fallon first met not on the SNL set, as some might assume, but at the 2002 MTV Video Music Awards, which Fallon was hosting. 

“The funny thing about our friendship even when it first started — I just remember that nothing was that serious," Timberlake said to Fallon during a 2020 Tonight Show interview. Soon after meeting, he later added, "We started doing bits back and forth, you know, and that's all we do now."

RELATED: Every Host of The Tonight Show Through the Years

While it's impossible to choose a favorite moment from their many hilarious appearances together on The Tonight Show and Late Night with Jimmy Fallon, we've rounded up 10 standouts that perfectly capture their comedic chemistry.  

Check out some of Justin Timberlake and Jimmy Fallon's best sketches and interview moments, below.

Justin Timberlake on The Tonight Show Starring Jimmy Fallon Episode 1910

"Classroom Instruments" with Justin Timberlake

Justin Timberlake, Jimmy Fallon & The Roots Sing "Selfish," "My Love" & More (Classroom Instruments)

Timberlake's January 25, 2024 Tonight Show visit was somehow the entertainer's first since 2021—but he made up for lost time with this excellent installment of "Classroom Instruments."

House band The Roots did most of the heavy (tiny?) lifting when it came to backing Timberlake on toy instruments, while Fallon held it down on the wood block. Timberlake clinked a blue triangle as he sang "Selfish," his lead single from his Everything I Thought It Was album, before transitioning into hits "Senorita," "SexyBack," "My Love," and "CAN'T STOP THE FEELING." 

RELATED: Justin Timberlake and Jimmy Fallon Teamed Up for a New Barry Gibb Talk Show Sketch on SNL - Watch

During their 2024 interview about Timberlake's first solo studio release in six years—collecting just 18 of the actual one hundred songs that were written, according to Timberlake—Fallon said, "I've never seen anyone work harder on anything in my life than you on this album."

"The only thing I work harder on is our relationship," Timberlake joked.

The Camp Winnipesaukee Boys sing "Ironic"

The braces-wearing, curly-wigged young Jimmy and Justin have sang so many classic hits while bunking down at Camp Winnipesaukee, from Toto's "Africa" to 4 Non Blonde's "What's Up"–including an adorably awkward take on "Ironic" by Alanis Morissette. 

"SexyBack" gets a barbershop version

The Ragtime Gals: "SexyBack"

One of Timberlake's biggest hits got the old-timey barbershop quartet treatment from the Jimmy Fallon's Ragtime Gals on Late Night in 2013, with Timberlake donning the red bowtie to sing lead. The harmonious results are as catchy as the original. 

Jimmy Fallon doesn't love Justin Timberlake's Jimmy Fallon impression

No one knows your quirky mannerisms like the people closest to you, and Timberlake and Fallon's friendship is no exception. 

The silent interview

Justin Timberlake Has a Silent Interview with Jimmy Fallon

Timberlake relied on meaningful facial expressions, gestures, and his natural rapport with Fallon to have a "talk" while on vocal rest. 

Timberlake and Fallon can't have a "Songversation" without cracking up

The original sung-conversation sketch is hilarious—and so is this blooper reel, which reveals the many tries it took to keep a straight face.

Steve Carell arm-handles Fallon

Real People, Fake Arms with Steve Carell and Justin Timberlake, Part 1

Real People, Fake Arms with Steve Carell and Justin Timberlake , Part 2

When The Office alum Steve Carell joined Timberlake and Fallon for an installment of "Real People, Fake Arms," he portrayed a tailor who needs to call on a fellow mannequin-armed "Suit & Tie" expert (that's Timberlake, in case you didn't get it). 

"Looks" with Will Ferrell

Timberlake and Ferrell serve some serious eye-acting in this sketch, which feels like the (wordless) indie bromance we never knew we needed. 

Three Michael McDonalds sing "Row, Row, Row, Your Boat"

That time Timberlake and Fallon served up their best impressions of the Doobie Brothers singer, joined by McDonald himself on Late Night in 2013.

RELATED: Millie Bobby Brown and Noah Schnapp Are Bestie Goals Playing This Tonight Show Game

Jessica Biel and Fallon take the "Best Friends Challenge"

Best Friends Challenge with Justin Timberlake and Jessica Biel

Who knows Timberlake better: His BFF Fallon, or his wife, Jessica Biel?


This Late Night sketch remains a riot, while also serving as a time capsule that captures the era circa 2013 when we all went around saying hashtags out loud. 

Originally published Aug 10, 2023.