Justin Timberlake's Complete Transformation

It's never been easy to describe Justin Timberlake. That's because he's never been or done just one thing. In a bustling entertainment scene where talents emerge from the screen, the stage, and social media, Timberlake easily stands out as a true multi-hyphenate. He is a singer, a boy band member, an actor, a producer, an environmentalist, a husband, and a father who continues to make headlines.

The Tennessee native has always done multiple endeavors at once, a juggling act that has been a constant feature of his long, award-winning career. So far, Timberlake has received 39 Grammy nominations and 10 wins, along with eight Emmy nods and four wins. Not to mention, he has also received both Golden Globe and Oscar nominations. Without a doubt, Timberlake is in a league of his own. A look at his transformation over the years reveals that he was always destined to be at the top.

Long before Hollywood ever heard of Justin Timberlake, he was a young boy who went to church. Raised a Baptist with a choir director for a dad, he eventually found himself joining the choir, as he sang at church regularly. This essentially marked his first public performance, and, for Timberlake, he wouldn't have done it any other way.

During an appearance on "The Late Show with Stephen Colbert," Timberlake and Colbert got into a discussion about choir singing after belting out a few lines of "The Star-Spangled Banner" together. When Colbert revealed he also once sang in the choir, Timberlake remarked, "So then you know that church is the best place to sing because you can go up there and completely botch anything. And then, at the end, everyone says, 'Amen.'" And, while it's unclear if Timberlake already had professional singing ambitions back then, he didn't stay an unknown talent for too long.

After spending his early years in the choir, Justin Timberlake was no longer a stranger to performing in public. His family also encouraged him to pursue music early on. "When the family found out I could sing, they were dressing me into country or gospel, because that's what was big in the area," Timberlake told Rolling Stone. Not long after getting started in gospel music, he was also ready to start competing, first joining the Mid-South Fair Junior Youth Talent Contest where Timberlake made it all the way to the finals at age 9.

By the time he was 11, Timberlake was already eyeing something bigger, particularly the famous competition show "Star Search" hosted by Ed McMahon. Back then, he made his way to Arden Studios to record a demo tape. Soon after, Timberlake learned he would have to miss school to appear on the show. "Justin, a straight-A sixth-grader at E. E. Jeter Elementary School in Shelby Forest, has received an excused absence from classes to be in Orlando Nov. 9 to tape the first show," a 1992 article read, according to Commercial Appeal. In the end, Timberlake performed onstage dressed as a cowboy and finished as a runner-up to Anna Nardona.

Shortly after his "Star Search" appearance, Justin Timberlake set his sights on Disney's "The All New Mickey Mouse Club." At the time, Disney was looking for young Mousketeers all over the U.S. and, in the end, cast the ones who stood out the most. In 1993, the standouts happened to be Christina Aguilera, Britney Spears, Ryan Gosling, and, of course, Timberlake. The gang was also joined by older stars Keri Russell and Timberlake's eventual bandmate, JC Chasez.

In Spears' memoir, "The Woman In Me," the singer shared how hard they all worked while on the show, sometimes practicing their choreography multiple times a day. That said, the stars also had time to bond. And it sounds like this is also how Spears' romance with Timberlake started. "[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me," Spears wrote in her memoir (via People). "A Janet Jackson song was playing in the background as he leaned in and kissed me." 

Timberlake would only star on "The All New Mickey Mouse Club" for two years before embarking on a new chapter in his career. As for Spears, she left the show in 1994. Years later, in 1999, she and Timberlake became an item.

As he entered his early teen years, Justin Timberlake was ready to become the next big pop sensation. Back in 1995, Chris Kirkpatrick was interested in forming a boy band in Florida, so he asked Timberlake as well as Joey Fatone, whom Kirkpatrick knew from his time working at Universal Studios. Timberlake also asked his former Mouseketeer pal, JC Chasez, to join them. The group met their final member, Lance Bass, through a vocal coach after their original bass singer left.

Together, they became known as NSYNC, and before the group became a hit in the U.S., they made quite a splash in Europe. On their tours, fans flocked wherever they went. "I was about 15 or 16 years old. We'd just given a concert in Germany at a festival on this huge field," Timberlake recalled in an interview with The Hollywood Reporter. "And we were in the tour bus afterward, driving on a dirt road, and I looked out the window and saw all these young, impressionable females running after the bus."

Over the years, NSYNC would be known for songs like "Tearin' Up My Heart," "Bye Bye Bye," "It's Gonna Be Me," and "I Want You Back." The group would also receive eight Grammy nods. After some time, however, Timberlake was ready to take the next step in his career once more.

In 2002, NSYNC was at the height of its success when the group suddenly announced they were taking a break. Around the same time, Timberlake surprised everyone by releasing his first solo album, "Justified," featuring songs including "Señorita," "Cry Me a River," and "Rock Your Body." During an interview with the New York Post in 2002, he talked about his musical influences — Donny Hathaway, Marvin Gaye, and Stevie Wonder — and how his album mixes hip-hop with R&B and what he referred to as "retro-rock."

And, while NSYNC fans initially assumed Timberlake would return to the group after the release of "Justified," this wasn't so. Eventually, it became clear that NYSNC was no more, with Lance Bass writing in his memoir, "Out of Sync" (via HuffPost), "We're definitely broken up. It's not a hiatus." Bass also singled out Timberlake, explaining that the singer didn't want to do another album with the group. Meanwhile, Joey Fatone later told Yahoo! Entertainment that, like the fans, he thought Timberlake would return after his "Justified" tour. However, by the time Timberlake took his album on the road, the guys started taking on solo projects of their own and never did get back together. Despite this, NSYNC never officially announced their breakup.

Just a year after releasing his "Justified" album, Justin Timberlake experienced major success as a solo artist. His first solo album debuted at No. 2 on the Billboard 200 charts. And, by 2003, the album had sold a reported 3 million copies. In an interview with Rolling Stone, Timberlake made it clear he wanted his fans to get over his boy band phase. More than anything, he wanted people to appreciate his distinct musicality and be more than a teen heartthrob. Timberlake also made it clear he had a lot of confidence in his solo album. "Do I think that what I've done with [Justified] is [10] times better than anything 'NSync has ever done? Yes, I do. But I'm a cocky bastard," he said.

Soon enough, Timberlake's solo act was, well, justified. Years after receiving a 1999 Grammy nod as a member of NSYNC, the singer won his first set of Grammys in 2003 for "Justified" and the song "Cry Me a River." He also made his solo Grammy performance debut with the Black Eyed Peas. Together, they sang a medley that included Timberlake's "Señorita" and the Black Eyed Peas' hits "Where Is the Love?" and "Funky Child." At that time, the new solo star looked unstoppable.

By 2004, Justin Timberlake and legendary pop sensation Janet Jackson weren't strangers to one another. After all, the two award-winning artists had collaborated, with Jackson lending vocals to Timberlake's song "(And She Said) Take Me Now." Soon, the new solo star joined Jackson at the 2004 Super Bowl half-time show. Timberlake would appear at the end of Jackson's set, with the likes of P. Diddy, Nelly, and Kid Rock having already appeared. With only Jackson remaining on stage with Timberlake, he sang "Rock Your Body." When he sang the final lyrics, "Bet I'll have you naked by the end of this song," Timberlake proceeded to rip a part of Jackson's wardrobe, revealing her breast for a brief moment.

Afterward, it was revealed that Jackson had suffered a wardrobe malfunction onstage and that Timberlake was only supposed to reveal another part of her outfit. That said, body piercer Byriah Dailey told USA Today that Jackson's stylist, Wayne Scot Lukas, had been shopping for nipple jewelry for the singer just before the Super Bowl and Lukas allegedly hinted, "There's going to be a surprise at the end." The Federal Communications Commission eventually launched an investigation into the incident. Meanwhile, Timberlake issued an apology before Jackson released hers. Years later, in 2018, Timberlake performed again at the Super Bowl LII half-time show.

Justin Timberlake was determined to keep his career in high gear despite the Super Bowl controversy. This time, he decided to focus on acting. After taking on some minor roles in the past, Timberlake returned to the big screen for the crime drama "Edison." Despite the big names in the cast, including Oscar-winner Morgan Freeman, now-disgraced actor Kevin Spacey, and rapper LL Cool J, the movie went straight to DVD.

That said, this didn't discourage Timberlake from signing on to more movie roles. Soon after, he joined the cast of Nick Cassavetes' "Alpha Dog," which also stars Bruce Willis, Emile Hirsch, and Anton Yelchin. Based on real-life events, the film tells the story of a drug dealer who kidnaps the 15-year-old brother of a man who owes him money, although the script changed some of the names.

In the movie, Timberlake plays Frankie Ballenbacher, a character whose real name is Jesse Rugge. To prepare for the role, the singer had to read a ton. "Literally, when we signed up for the project, we all got a stack of files. It was thick. I mean literally like a novel of files of all the police reports and all the newspaper reports about what had happened," he told Movie Web.

Around the time that Justin Timberlake was busy doing movies, the singer also found lasting love, although the whole story is not as romantic as it sounds. In 2007, Timberlake met actor Jessica Biel at a party, and, while Timberlake was smitten with her, Biel wasn't interested in reciprocating his feelings. "I had to be pretty persistent in order to get her to say yes," Timberlake later told Us Weekly.

Eventually, Timberlake's efforts paid off, and Biel agreed to go out with him. The two remained together for years before splitting in 2011. Later that year, however, Biel and Timberlake got back together and became engaged that December. Less than a year later, the couple tied the knot in an intimate ceremony in Italy. As Biel walked down the aisle, Timberlake serenaded her with a special song he had written for her. "I figured if there was something I was going to be able to offer, it would be to sing her down the aisle," the singer later told People. The moment made Biel and the rest of the wedding party tear up.

In the years that followed, Justin Timberlake pursued movie roles as much as he did music. In 2010, David Fincher released his Oscar-winning drama, "The Social Network" where the singer portrays Napster founder Sean Parker as he goes toe-to-toe with Facebook co-founder Mark Zuckerberg. In the movie, Zuckerberg is portrayed by seasoned actor Jesse Eisenberg, and some wondered if a newbie actor like Timberlake would struggle to keep up with Eisenberg onscreen. Luckily, they worked the whole thing out during rehearsals.

In the years that followed, Timberlake also starred in the romantic comedy "Bad Teacher" with ex-girlfriend Cameron Diaz. He soon followed this up with "Friends with Benefits" where he stars opposite Mila Kunis. Timberlake fought for the film to get an R-rating. It was also a challenge for the singer/actor to get his character's onscreen relationship with Kunis' character right. "They have to be an even match," Timberlake told The Guardian. "There's a way to do naughty. You can do crass if you're witty at the same time." Later on, the singer would also take on the starring role in the animated "Trolls" franchise, which would earn him his first Oscar nod.

While busy with both movie and music projects, Justin Timberlake and Jessica Biel also became parents. In 2015, the couple welcomed their first child, son Silas Randall Timberlake, who takes his name from Timberlake's maternal grandfather, Bill Silas Bomar. And, while the couple kept the details of Silas' birth private, Biel later went on "Today" to gush about their little one and Timberlake's daddy skills. Asked whether Timberlake is involved in late-night feedings and changing diapers, Biel revealed, "He is in there, deep." Meanwhile, in an interview with The Hollywood Reporter, the singer spoke candidly about life as a new father, admitting that he struggled to balance family life and work, especially during their baby's first eight months.

A few years later, in 2020, the couple welcomed their second son, Phineas. Because Biel gave birth to their second child just as hospitals changed their restrictions regarding guests, this allowed Timberlake to be present for their son's delivery.

Just when it seemed like NSYNC would never reunite and fans had just about given up, Timberlake and his NSYNC buddies confirmed that they were, in fact, getting the band back together. It seems the much-awaited reunion was teased as far back as March 2023 when Universal Pictures released a trailer for Timberlake's movie, "Trolls Band Together." In the film, Branch's (Timberlake) long-lost brother, Floyd (Troye Sivan), appears out of nowhere to convince Branch to get their old boy band, BroZone, back together. The trailer also references various male pop groups such as Boyz II Men, One Direction, Backstreet Boys, and, of course, NSYNC.

Months later, in September, NSYNC posted a video to Instagram of the five group members in an elevator together. As it turns out, the guys were about to make an appearance at the MTV VMAs to present the Best Pop Award to Taylor Swift. Once onstage, Swift couldn't help but ask what the group would do next. On September 14, NSYNC confirmed on Instagram that they were releasing a new single entitled "Better Place," which is featured on the "Trolls Band Together" soundtrack.