Wonder Wheel
Jessica Miglio/Amazon Studios
November 30, 2017 08:45 AM

Justin Timberlake is that rare superstar combo: a celebrated singer who’s also a popular actor. Hot off of the heels of being announced as next year’s Super Bowl Halftime performer, he’ll soon be seen going up against Oscar winner Kate Winslet in Woody Allen’s Wonder Wheel.

How did a former ‘NSYNC boy band member end up in a film with mounting Oscar buzz? Here’s a look at the 36-year-old’s evolution from singer to thespian.

From the Mickey Mouse Club to ‘NSYNC

As a kid in 1983, the Memphis-native sang country songs on the singing competition show Star Search.

Mickey Mouse Club

Although he didn’t win, the show’s exposure led him to be cast in The All New Mickey Mouse Club in 1989, with a cast featuring future actors Ryan Gosling and Keri Russell, as well as soon-to-be pop stars Christina Aguilera, Britney Spears and J.C. Chasez — who later became one of his ‘NSYNC bandmates.

When the show ended in 1994, producer Lou Pearlman recruited Timberlake and Chasez to join three others and form ‘NSYNC. The boy band’s self-titled debut album — released in 1998 — peaked at No. 2 on the charts, and featured hits like “I Want You Back” and “Tearing At My Heart.”

The group’s swoon-worthy lyrics, catchy choruses and syncopated dance routines stole the hearts of many teenage girls, and their second album No Strings debuted at No. 1, selling a record 2.4 million copies in its first week and later becoming the top selling album of the 2000s, according to Rolling Stone. Its most notable singles included “It’s Gonna Be Me” and “Bye, Bye, Bye.”

The Early 2000s: Going Solo and That “Wardrobe Malfunction”

After just one more album — Celebrity — with the boy band, Timberlake launched his solo career in 2002 with Justified. Featuring hits “Rock Your Body,” “Cry Me a River” and “Like I Love You,” the album sold over 1.9 million copies, according to Official Charts.

Justin Timberlake and Janet Jackson
Frank Micelotta/Getty Images

Just two years later, Timberlake performed as a surprise guest at the 2004 Super Bowl, making history for the infamous “wardrobe malfunction” where he ripped off part of Janet Jackson‘s leather costume and revealed her breast on live television. The pop-star’s apology at the subsequent Grammy Awards turned the phrase “wardrobe malfunction” into a common pop-culture reference.

With the announcement that Timberlake will perform again at the Super Bowl Halftime show in 2018, the incident has been brought back into the limelight. Fans across the U.S. reacted with a mix of humor and disapproval.

Making It to the Big Screen

As his music career took off, Timberlake made guest appearances in episodes on TV series like The Wonderful World of Disney (in 2000) and Top of the Pops (in 2002). He also had small parts in a few films, including Model Behavior (2000), Longshot (2001) and Edison (2005). He upgraded to big screen roles in 2006.

In 2006, Timberlake was filming two movies while also creating FutureSex/LoveSounds — his second solo album — and all three works were released that year. Timberlake appeared in films Alpha Dog (with Emile Hirsch) and Black Snake Moan (with Samuel L. Jackson and Christina Ricci).

But unlike many singers-turned-actors, Timberlake’s shift was well-received. He netted nominations for the “Breakout Male” Teen Choice Award for his performance in Black Snake Moan, and the “Best Breakthrough Performance” MTV Movie Award for his performance in Alpha Dog.

Grabbing a Seat at the Oscars

From 2006 to 2013, Timberlake made his acting career his primary focus. He voiced Artie in Shrek the Third (2007), appeared alongside Jessica Simpson and Jessica Alba in The Love Guru (2008) and had a starring role opposite Jeff Bridges in The Open Road (2009).

Timberlake had his biggest film breakthrough in 2010 when he appeared as Napster founder Sean Parker in The Social Network, which won Oscar awards for Best Writing Adapted Screenplay, Best Original Music Score and Best Film Editing.

Romantic Comedy Leading Man

It seems natural that the dreamy singer of songs like “Sexyback” and “Mirrors” would star in romantic comedies. Timberlake’s first starring rom com role was in 2011’s Bad Teacher, where he played a very awkward — and hilarious — middle school teacher.

Cameron Diaz and Justin Timberlake
Dave Allocca/Startraks

The project piqued the interest of Timberlake’s fans because his on-screen love interest, Cameron Diaz, also happened to be the actor’s real life ex-girlfriend. While filming the comedy, Timberlake was busy dating his soon-to-be wife Jessica Biel.

That same year, Timberlake starred opposite Bad Moms actress Mila Kunis in the romantic comedy Friends with Benefits.

Combining His Talents in Trolls

In 2013, Timberlake released his most recent album — The 20/20 Experience — which spawned hits like single “Mirrors” and Jay-Z collaboration “Suit & Tie.” The album was the best-selling record of 2013, according to Nielsen SoundScan.

Just a few years later, Timberlake returned to Hollywood. He combined his talents of acting and music in the 2016 DreamWorks Animation movie Trolls.

Justin Timberlake promoting Trolls
Don Arnold/WireImage

The film’s hit song “Can’t Stop the Feeling,” featuring Timberlake, won an Oscar nomination for Best Achievement in Music Written for Motion Pictures, and a Golden Globe nomination for Best Original Song in a Motion Picture.

Beyond writing and singing “Can’t Stop the Feeling” for the film, Timberlake was its executive music producer and voiced one of its lead characters.

RELATED VIDEO: Justin Timberlake & Jessica Biel Enjoy Date Night at Game 2 of World Series — See More Celebs in the Crowd!

Working with Kate Winslet in Wonder Wheel

In an interview with Entertainment Weekly in August, Winslet revealed that her and Timberlake got along great as costars.

Justin Timberlake and Kate Winslet
Todd Williamson/JanuaryImages/Shutterstock

“He’s totally unvain, he has an absolutely infuriating ability to learn lines fast, and he’s an all around great person — humble, fun, hard-working, easygoing, no ego,” said the 42-year-old actress. “Such a joy, really.”

 Wonder Wheel opens Dec. 1

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