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  3. Justin Timberlake's Best Moments

Justin Timberlake's Best Moments

By Madeline Boardman Updated April 04, 2016 at 01:12 PM EDT
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Justin Timberlake's Best Moments

Justin Timberlake's Best Moments
Credit: Instagram; Larry Busacca/WireImage; Jeffrey Mayer/WireImage; Dana Edelson/NBC

Born in Memphis on Jan. 31, 1981, renaissance man Justin Timberlake truly just gets better with age. From his teeny bopper days to his first weeks of fatherhood, see Timberlake's best moments, ahead.

 

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The time he was a Mouseketeer with Ryan Gosling

Ryan Gosling and Justin Timberlake
Credit: Walt Disney Co./Courtesy Everett Collection

In the early 1990s, a young Timberlake joined the Mickey Mouse Club and became friends with a fellow Mouseketeer by the name of Ryan Gosling. The two future hunks spent tons of time together, as Timberlake explained to Ellen DeGeneres on The Ellen Show in 2011, "Funny enough, [Gosling's] mother had to keep her job in Canada the second year that we were on the television show and my mom was his guardian for like six months. We actually lived together when we were that age. So we were probably a little closer that the rest of the kids that were on the show just because we had to share a bathroom."

 

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When he was in sync with *NSYNC

When he was in sync with *NSYNC
Credit: Larry Busacca/WireImage

There's only one way to top a stint with MMC, and that's as the resident hunk in a boy band. Teaming up with Chris Kirkpatrick, Joey Fatone, JC Chasez, and Lance Bass, Timberlake debuted "I Want You Back" in the late '90s. The rest is pop history.

 

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When he debuted this iconic look with Britney Spears

2001: The AMAs red carpet, With Justin Timberlake
Credit: Jeffrey Mayer/WireImage

Timberlake stepped out with his then-girlfriend Britney Spears at the 28th Annual American Music Awards in January 2001, and rocked a getup almost as famous as the relationship itself. In a now-infamous sartorial moment, the two wore matching all-denim outfits, complete with a jean purse on Spears and a questionable denim cowboy hat on Timberlake.

 

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That time he went solo

That time he went solo

While it signaled the tragic end of *NSYNC, Timberlake's solo career was its own kind of blessing. In a move that would make Adele proud, the singer took inspiration from his split with Spears for the 2002 debut studio album Justified, even going so far as to recruit a Britney lookalike for the music video to the hit single "Cry Me a River."

 

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That time he cried over his dogs

That time he cried over his dogs
Credit: MTV

Back when Ashton Kutcher was the rabble-rousing host of Punk'd, he brought Timberlake into the pranks for a 2003 episode of the show. With help from some actors impersonating FBI agents, the That '70s Show star convinced Timberlake that he owed nearly $1 million in back taxes and all of his valuables were being confiscated as a result. The seized items included Timberlake's dogs, making the pop star tear up at the news. Being the charmer that he is, he took it in stride when Kutcher revealed that the incident was all a joke.

 

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When he redefined the Christmas present

When he redefined the Christmas present
Credit: Dana Edelson/NBC/NBCU Photo Bank via Getty Images

One of the few Saturday Night Live hosts who nearly outdoes the cast members, Timberlake teamed up with The Lonely Island for a 2006 episode of the sketch show. Crooning alongside Andy Samberg, Timberlake offered up his "Dick in a Box," wearing a wrapped present on his body for what would become one of the most famous bits in SNL history.

 

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When a million dollars wasn’t cool

When a million dollars wasn’t cool
Credit: Merrick Morton/Columbia Pictures

After appearing in 2006's Alpha Dog, Timberlake was a part of an Oscar-winning project with the 2010 debut of The Social Network. The singer made a celebrated turn as Napster founder Sean Parker, and captivated viewers with his diatribe on Victoria's Secret and his uttering of the quotable line, "A million dollars isn't cool, you know what's cool?... A billion dollars."

 

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That time he taught us the history of rap

That time he taught us the history of rap
Credit: Douglas Gorenstein/NBC/NBCU Photo Bank

There are few greater combinations than Justin Timberlake and Jimmy Fallon. The frequent collaborators debuted a bit on the history of rap music for the first time in 2010, taking Tonight Show viewers from "Rapper's Delight" to "Empire State of Mind." Because once is never enough, they've done the sketch five more times in the years since, mixing it up with dance move evolution performances and sit-down chats.

 

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When he brought it on down to wrappinville

When he brought it on down to wrappinville
Credit: NBC

After hosting SNL five times, Timberlake appeared on a 2013 episode as a musical guest, alongside his pal, host Fallon. He could hardly sing on the show without getting in on the fun, so he slipped into an oversized costume to act as a mascot for a wrapping store — just one of many bits the star has made famous.

 

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When he brought his mom to the Oscars

When he brought his mom to the Oscars
Credit: Kevin Mazur/WireImage

Timberlake presented at the 2011 Oscars with his Friends With Benefits costar Mila Kunis, and decided to bring his mother as his date for the star-studded ceremony. He walked the red carpet outside of Los Angeles' Kodak Theatre with his mom Lynn on his arm, calling her "gorgeous" in interviews with reporters before the show.

 

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When he thanked Jessica Biel

When he thanked Jessica Biel
Credit: Kevin Mazur/Getty Images

Timberlake had a big moment in 2015, when he was inducted into the Memphis Musical Hall of Fame in his hometown. Getting emotional at the honor, he took the chance to thank his wife Jessica Biel for her support. He teared up as he said, "Baby, I love you more than I could put into words and more than any song I could ever write."

 

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That time he flexed on Father’s Day

That time he flexed on Father’s Day
Credit: Instagram.com/justintimberlake

After nearly three years of marriage, Timberlake and Biel welcomed their first child together in April 2015. The pop star celebrated his first Father's Day a few months later, posting a photo with his young son Silas and captioning the shot, "FLEXIN' on Fathers Day... #HappyFathersDay to ALL of the Dads out there from the newest member of the Daddy Fraternity!!"

 

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    1 of 13 Justin Timberlake's Best Moments
    2 of 13 The time he was a Mouseketeer with Ryan Gosling
    3 of 13 When he was in sync with *NSYNC
    4 of 13 When he debuted this iconic look with Britney Spears
    5 of 13 That time he went solo
    6 of 13 That time he cried over his dogs
    7 of 13 When he redefined the Christmas present
    8 of 13 When a million dollars wasn’t cool
    9 of 13 That time he taught us the history of rap
    10 of 13 When he brought it on down to wrappinville
    11 of 13 When he brought his mom to the Oscars
    12 of 13 When he thanked Jessica Biel
    13 of 13 That time he flexed on Father’s Day

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