Justin Timberlake: A Look At The Pop Star's Incredible Transformation

The days of "Bye Bye Bye" bumping through our Sony Walkmans may be gone — but never forgotten. Instead, Justin Timberlake and the rest of the NSYNC gang top the early 2000s throwback playlists on Spotify, taking us back to the days when boy bands and head-to-toe-denim characterized the turn of the century. While we could sit and chat about all five members of the iconic musical group that was NSYNC, everyone knows that every boy band has its chosen leader. After all, what was One Direction without Harry Styles? In short, Timberlake was the face of NSYNC, and like many aspiring solo artists before him, he later ditched his bandmates to become one of the music industry's most successful solo artists.

The "SexyBack" singer was dubbed "America's Golden Boy," quickly becoming a pop sensation with ambition and drive to sustain his solo career for decades to come. While Timberlake's talented vocals made him a multi-Grammy-Award-winning artist, he's got quite a set of acting and comedy chops, as well, and his guest appearances on "Saturday Night Live" have led to several Emmys. Meanwhile, his personal life and relationships also took center stage. The pop star's romantic life has been the subject of tabloid fodder ever since his days of bleached curls and turtleneck sweaters (and his iconic matching denim outfit with Britney Spears, obviously). From crying a river to his married life with Jessica Biel, the "Summer Love" singer has come a long way from his days as a teenage heartthrob. 

We're breaking down Justin Timberlake's incredible transformation.

Justin Timberlake was influenced by music at a young age, with his own father being a Baptist church choir director. The "Can't Stop the Feeling" artist spent his early days in a town called Shelby Forest, which is about 13 miles north of Memphis, Tennessee. Before he was bringing sexy back, Timberlake was singing "Hallelujah" in the church choir where he first honed in on his vocal skills. 

The future pop superstar continued to be surrounded by musical influences as a kid, including his grandfather, who'd once played guitar with Elvis Presley (no big deal). After learning guitar himself, a young Timberlake listened to an eclectic range of music, courtesy of his elders, including the works of legends, such as Willie Nelson, Johnny Cash, and B.B. King, rock influences like the Eagles and Queen, and those who reigned during Hollywood's Golden Age, from Gene Kelly and Fred Astaire to Frank Sinatra and Dean Martin. He also began taking voice lessons at age 8 with Bob Westbrook in Memphis, who told CNN of the youngster's clear star qualities, "Just his mannerisms and his charisma, his hair, the whole bit, his natural stage feel."

His humble beginnings in the South would later be eclipsed by his skyrocket to fame during his teens. In 2017, Timberlake admitted to The Hollywood Reporter that those days feel nonexistent. "I have some faint images from my childhood, but no, I can't really remember not being famous," he recollected (via ET).

Before Justin Timberlake was a household name, he was a kid in a cowboy hat hoping to win the television program "Star Search." The show took young aspiring artists from around the United States performing against each other in front of judges and a live audience in the hopes of walking away as America's newest star. Timberlake, who competed under the moniker Justin Randall, is one of many future A-listers to have debuted on the talent program, including Britney Spears, Beyoncé, Usher, Christina Aguilera, and LeAnn Rimes.

The "Like I Love You" singer was 11 years old when he performed his rendition of Alan Jackson's "Love's Got a Hold on You" in 1992, and he ended up taking second place during his appearance. Timberlake was beaten by fellow contestant Anna Nardona. During a "Where are They Now?" segment on "The Early Show," reporters tracked down Nardona, who admitted it wasn't until VH1 notified her in the early 2000s that she realized it was the former NSYNC member she took out of the competition. While she admitted she was proud to have taken home the prize against Timberlake, she ended up leading a life outside of the spotlight.

For his part, Timberlake reflected on his time on "Star Search" during a January 2023 interview on "The Graham Norton Show" with happy — yet cringe-worthy — memories. Admitting it was more of a television show than an actual talent search, he joked: "It was a wonderful, wonderful experience. That was my first hip-shake on TV — highly inappropriate."

Like several other celebrities, Justin Timberlake got his start as a performer on "The All-New Mickey Mouse Club." The show was a re-boot of the 1950s series that featured comedy skits, music videos, notable guests, and several live performances by young up-and-coming stars. Having landed a gig as a cast member shortly after earning runner-up on "Star Search," Timberlake was joined by Britney Spears, future NSYNC bandmate JC Chasez, Ryan Gosling, and Christina Aguilera during his 1993-1994 tenure.

In 2017, Timberlake admitted the experience acted as a kind of boot camp for wannabe multi-talents, telling The Hollywood Reporter (via Insider), "We were at the age when you just soak in everything." He further explained, "We were taking acting classes, music classes, dance classes. We were learning how coverage and editing and cinematography work. And being put in front of a live audience, learning how to engage the crowd to get a laugh. Honestly, it was like 'SNL' for children."

And so, Timberlake was able to prepare for what would be an epic future career, despite his pre-teen attitude. "I was a little punka**," he previously admitted to Rolling Stone. "But I really started to find myself there. It was a good experience. After that, I went back to school for a year and got into trouble — mailbox bashing and just being a delinquent." Timberlake went on to quip, "I'm just glad I didn't have to go to regular high school. I would have gotten arrested by now."

Five men with epic hairstyles, harmonic vocals, and an ability to pack stadiums with thousands of screaming girls have a special place in our nostalgic hearts. We're talking about NSYNC, obviously, the boy band who rose to fame at the turn of the century and catapulted the solo career of Justin Timberlake. The iconic music group was born in 1996 after Chris Kirkpatrick just failed to land a spot in the Backstreet Boys and suggested that music mogul Lou Pearlman put together another boy band. Eventually, a 14-year-old Timberlake, as well as JC Chasez, Joey Fatone, and Lance Bass, would join the NSYNC ranks.

From there, NSYNC was an overnight sensation overseas, with their self-titled debut album topping the European charts in 1997 — the success eventually landed the group of stateside deal with RCA records and a re-release of the record in the U.S. A year later, the "I Want You Back" hitmakers gained similar popularity in the states and eventually dropped their sophomore album "No Strings Attached" in 2000. The record shattered expectations, selling 2.4 million copies in its first week. Alongside the Backstreet Boys, NSYNC's massive success ushered in the new wave of boy bands.

In a 1998 Rolling Stone feature, Chasez dubbed Timberlake "the All-American guy," while Timberlake noted of the alleged BSB vs. NSYNC rivalry, "People try to make a feud out of everything. And we didn't even see it like that."

Just as their matching head-to-toe denim outfits live forever in our memories, so does the highly publicized relationship between Britney Spears and Justin Timberlake. Decades later, these two are still making headlines for seemingly salacious details of what really went down in their three years together.

After first meeting as kids while starring in "The All New Mickey Mouse Club," Timberlake and Spears went on to date as their respective singing careers exploded. When they got together in 1999, it marked the beginning of a whirlwind media sensation. "I was in love with her from the start," Timberlake later told GQ (via Insider). "I was infatuated with her from the moment I saw her." However, rumors of infidelity on both sides plagued the relationship until the pair finally called it quits in 2002. 

With the breakup itself becoming a tabloid fixture, many reports alleged that Spears was to blame. That November, Timberlake's iconic "Cry Me a River" video alluded to infidelity, featuring a Spears look-alike getting into a car with another man, adding fuel to the blazing fire. In a 2003 "Primetime" interview, Diane Sawyer infamously asked her, "You did something that caused him so much pain. So much suffering. What did you do?" At the same time, Timberlake was celebrated, often taking jabs at Spears during interviews and openly talking about their former sex life, for which he publicly apologized on Instagram in 2021. More on this below.

After over 70 million records sold, worldwide tours, and who knows how much hair gel later, NSYNC stepped away from the stage in 2002. At the time, Justin Timberlake assured fans that the boy band was simply on pause and would be back to deliver more hits. The announcement came just days before Timberlake released his solo debut "Justified." "The break we're on was a conscious move. We all wanted to do it, and we were ready to do it," he told the New York Post. "Performing at stadiums every night for 50,000 fans takes a little out of you. I was 14 when we started, and we've been touring for the last seven years. The time was right; we were all in the same zone. This album is what I wanted to do."

However, as Lance Bass revealed in his 2007 memoir "Out of Sync," it was less of a hiatus and more of an official breakup. He added (via HuffPost), "Justin made it clear that he wouldn't be interested in discussing another album any time soon." Timberlake later admitted to The Hollywood Reporter (via Us Weekly), "I felt like I cared more about the music than some of the other people in the group. And I felt like I had other music I wanted to make and that I needed to follow my heart."

That said, in September 2023, NSYNC was still generating similar excitement from fans as they did during the Y2K era, when they finally reunited to drop their "Better Place" track.

Justin Timberlake's decision to break away from NSYNC clearly served him well. When he dropped his first single as a solo artist, 2002's "Like I Love You," it rose to a respectable No. 11 on the Billboard Hot 100. That fall, he released his debut album "Justified," which was met with rave reviews due to solid hits like "Cry Me a River" and "Rock Your Body." These tracks would not only solidify him as a solo act, but also helped earn Timberlake his first two Grammy wins. 

In 2003, Rolling Stone dubbed him "The New King of Pop." The former boy band singer told the outlet, "I know people have an image of me in their head, but I want them to be able to see past that. I want them to see the musicality of what I'm doing. ... And it's been proven." Timberlake added, "There's a weight lifted off my shoulders. I don't have to worry about that part anymore."

The "Mirrors" singer then dodged the sophomore curse with "FutureSex/LoveSounds" in 2006, on which he collaborated with Timbaland for the hit track "What Goes Around... Comes Around." His other massive single off the record, "SexyBack," rose to the top spot on the Billboard Hot 100 chart. Timberlake's global tour in support of the record was ranked 2007's third highest-grossing tour. As of this writing, Timberlake's gone on to produce two more studio albums, 2013's "The 20/20 Experience" and 2018's "Man of the Woods," while racking up 39 Grammy nominations and 10 wins for his discography.

The 2004 Super Bowl halftime show will forever be one of the most controversial moments in pop culture history. Justin Timberlake and Janet Jackson's performance went off without a hitch until a planned costume reveal left Jackson's breast exposed for 9/16th of a second. As the pair performed "Rock Your Body," Timberlake pulled away Jackson's bustier while singing, "Better have you naked by the end of this song." It was later revealed that the "SexyBack" singer's move was supposed to only reveal the red bra underneath the corset, but it ultimately went awry. 

While Jackson reportedly left the stage in tears, Timberlake later gave interviews joking about the incident. Both Timberlake and Jackson released statements apologizing for what happened, but it was the "Control" icon who took a huge career hit. Jackson was ousted from that year's Grammy Awards, and her "Damita Jo" album flopped. Meanwhile, Timberlake's star continued to rise: He was allowed to perform at the awards show, where he won his first two Grammys. 

In 2021, Timberlake apologized for his part in what many considered to be the star having an unfair, sexist advantage in the fallout. "I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. ... I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed," he shared in part on Instagram.

After his breakup with Britney Spears, Justin Timberlake went on to date Cameron Diaz from 2003 to 2006. The two ended up splitting amicably, even starring in "Bad Teacher" together in 2011. In 2007, Timberlake found love with his future wife, Jessica Biel. While the pair separated for a few months in 2011, they rekindled their romance later that year. After the "Mirrors" singer popped the question at the start of 2012, the two tied the knot that fall. 

Timberlake has gushed about his wife over the years, telling Vanity Fair in 2011: "She is the single-handedly most significant person in my life. In my 30 years, she is the most special person, OK? I don't want to say much more, because I have to protect things that are dear to me — for instance, her." And while the Grammy winner has been tied to several A-listers over the years and dealt with the very public fall-out from his relationship with Spears, it seems all the ups and downs were worth it. 

"Every once in a while, I can catch a glimpse of her when she doesn't see me looking, and I have this moment where I'm like, 'If you never make a good decision ... if you only make bad decisions for the rest of your life, you made one really good decision,'" Timberlake said of Biel on "The Ellen DeGeneres Show" (vis Life & Style) in 2013. "... It's nice to marry your best friend. It suits me."

Justin Timberlake has starred in several films throughout his career, but he hasn't exactly been proud of all of them. Timberlake got his start in acting as his solo career took off, starring in films like "Edison," "Alpha Dog," and "The Love Guru," but they were generally met with lackluster reviews. It wasn't until the singer took on the role of Sean Parker in the 2010 film "The Social Network" that he got to truly show off his acting skills. 

The biographical drama tells the story of Mark Zuckerberg's (Jesse Eisenberg) founding of Facebook. Timberlake's character is the founder of the website Napster, which allowed users to share music without copyright infringement rules. "When Napster hit the scene, I was 19 or 20," he told RogerEbert.com. "I had mixed feelings about it because I was the same age as all of those college kids that ended up playing the role of defendants in court." Timberlake admitted, "Had I not been in the music industry, I probably would have used it. At the same time, I was watching friends in the industry who were songwriters and were forced take up new jobs."

The David Fincher film, of course, was met with rave reviews and was nominated for several Oscars, including best picture. It also marked a turning point for Timberlake, who believes it changed his on-screen prospects. "There are two parts to my acting career," he told The Hollywood Reporter (via Insider), "before 'The Social Network' and after."

"America's Golden Boy" is also a big momma's boy. Justin Timberlake hasn't been shy about his close relationship with his mother, even opting to take mom Lynn Harless to the 2011 Academy Awards instead of his then-girlfriend and now-wife, Jessica Biel. Speaking to "Access Hollywood" on the red carpet at the event, the singer, who'd attended to present some awards alongside "Friends with Benefits" co-star Mila Kunis, admitted: "[The decision] was unanimous in my mind. For me, this is one of the coolest things ever, it's the first time I've ever been here like this, and so, I think we want to remember the night. ... You gotta bring your mom."

Their sweet relationship has lasted the tests of time — and the dog-eat-dog-world of Hollywood. At the height of his NSYNC success, a young Timberlake told Rolling Stone in 2001, "There's nothing in this world that I've done that my mother does not know about." So, it was only right for the "Rock Your Body" singer to include his mother in a first-look video for his hit song "Can't Stop the Feeling" in 2016. Along with Gwen Stefani, James Corden, and Anna Kendrick, Timberlake featured a number of his close friends in the video singing and dancing along to the track. In the clip, Harless can be spotted in a fuchsia tie-dye shirt jamming out to her son's single. Aw, mom's really do know best — right Justin?

A few years after tying the knot with Jessica Biel, Justin Timberlake and his wife welcomed their first son, Silas Randall, in 2015. The birth didn't go as planned, however, as the couple revealed in the 2018 book "The Nanny Connie Way: Secrets to Mastering the First Four Months of Parenthood," per Vogue. The pair admitted that all their labor training couldn't have prepared them for life's unexpected moments, writing, "When all our plans fell apart and the serene, natural childbirth we had envisioned ended with a transfer to the hospital and an emergency C-section, we arrived home exhausted, disillusioned, and totally in shock."

Silas eventually arrived as a healthy baby despite the unexpected C-section. Timberlake, however, had no idea just how much of a taxing job fatherhood could be. "At first, it broke me down," he told The Hollywood Reporter (via People). "Those first eight months felt like those old [Ed Sullivan] shows where people are balancing spinning plates on poles — except if you drop one, they die."

Ultimately, Timberlake found his footing, and even told "Today" how fatherhood had changed his music career, saying of Silas' impact, "I would have never written a song like 'Can't Stop the Feeling.'" In 2020, Timberlake and Biel quietly welcomed their second son, Phineas, in Montana amid COVID-19 lockdowns. As the pop star later gushed to Ellen DeGeneres of their growing brood, "We're thrilled and couldn't be happier. Very grateful."

Who's crying a river this time around? After being publicly shamed for reportedly cheating on Justin Timberlake decades ago, Britney Spears appeared to finally set the record straight in her 2023 memoir "The Woman in Me." While Spears ultimately confessed being unfaithful, she also claimed that Timberlake had cheated first. According to The U.S. Sun, the "Toxic" hitmaker revealed that she'd kissed her backup dancer, Wade Robson. In excerpts published by Entertainment Weekly, she alleged, "There were a couple times during our relationship when I knew Justin had cheated on me." She referenced paparazzi photos from 2000 that caught Timberlake sneaking around with former All Saints singer Nicole Appleton in London. "But I never said anything," Spears wrote. "At the time we'd only been together for a year." 

As of this writing, Timberlake has made no comment on the cheating allegations. However, an insider told People, "He's happy at home with Jess and their kids and he's focusing on new music. He's in such a great place."

That said, this is not the only time Timberlake has been accused of stepping out on a relationship. The singer was infamously photographed during a night out in New Orleans getting cozy and holding hands with "Palmer" co-star and on-screen love interest Alisha Wainwright in 2019, per The Sun. Timberlake later denied being unfaithful to wife Jessica Biel in an Instagram statement. Calling the incident "a strong lapse in judgement," he wrote, "I apologize to my amazing wife and family for putting them through such an embarrassing situation."

Amid the #FreeBritney movement, fans were outraged at resurfaced disparaging comments Justin Timberlake made about Britney Spears. "I don't know that person anymore. I'm not sure I knew her before," he told journalist Robert Haskell in 2006, as shared on X, formerly Twitter. "If I was writing an article about her, I would not be able to fight the urge to write every dirty thing about her." Timberlake also joked about their sex life. Bursting out laughing when Barbara Walters asked if he and Spears remained celibate during their relationship, he later told Hot 97 (via the Mirror), "I did it. I'm dirty. I'm in so much damn trouble, man. I'm going to get calls from my mother!"

In his apology statement to both Spears and Janet Jackson on Instagram, Timberlake acknowledged the subsequent backlash, admitting, "I understand that I fell short in these moments ... and benefited from a system that condones misogyny and racism." However, the backlash continued when Spears opened up about having an abortion when she and Timberlake were 19 in her "The Woman in Me" memoir. "I don't know if that was the right decision," she wrote (via Page Six). "If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn't want to be a father." 

While Timberlake has yet to directly respond to these claims, a source told Us Weekly, "He's trying to distance himself from her upcoming book. ... He would like to leave anything that happened in the past behind them."