Justin Timberlake: Career highs and lows

Justin Timberlake has many fans, along with a few haters. The latter of whom probably aren’t crying a river for the pop singer right now.

From a fresh-faced Disney Mouseketeer to a breakout member of NSYNC turned-solo-artist and movie star, Timberlake has had an impressive career spanning three decades. He’s also had more than one moment in an unflattering spotlight.

Timberlake survived the public scrutiny about his personal life that follows handsome tripple-threats on their rise to fame, an infamous Super Bowl debacle, and, until Tuesday, he made it to age 43 without a mug shot.

His arrest in New York for allegedly driving while intoxicated brought out ugly schadenfreude on social media from those who view the incident in which no one was hurt as some sort of pop culture karmic retribution. Timberlake, to them, is perhaps paying for his perceived past treatment of both his former girlfriend Britney Spears and fellow performer Janet Jackson. Some of the same people, undoubtedly, who helped streams of Spears’ 2011 single “Criminal” spike after Timberlake’s arrest.

Here’s a look back at some of Timberlake’s high and low career moments.

Finding love on the job

Most boy bands usually have a standout member. Then curly-haired Timberlake vied with JC Chasez for that title when the two, along with Chris Kirkpatrick, Joey Fatone and Lance Bass, came together as NSYNC back in 1995.

With hits like “I Want You Back,” “Tearin’ Up My Heart,” “Bye Bye Bye” and “It’s Gonna Be Me,” NSYNC rode of wave of popularity in the late ’90s to become one of the most successful male vocal groups of all time.

So it was a match made in paparazzi heaven when Timberlake started dating fellow pop star Britney Spears. The pair first met on the set of “Mickey Mouse Club” and they reunited in 1998, when Spears opened for NSYNC on tour.

Spears and Timberlake made their first public appearance as a couple when they sat together at the 2000 MTV Video Music Awards, and it wasn’t long before they were memorably wearing matching denim outfits on the red carpet.

Britney Spears and then-boyfriend Justin Timberlake arrive at the premiere of her movie “Crossroads” in 2002. (Kevin Winter / Getty Images)

In fact, 2001 was a big year for the couple: They performed together during the Super Bowl XXXV halftime show, Spears had an iconic performance with an albino Burmese python at the MTV Video Music Awards and it was revealed that she and Timberlake were living together.

But they broke up the following year.

Timberlake appeared to be pointing fingers at Spears when he released his single “Cry Me a River,” which focused on infidelity and featured a Spears look alike in the music video. Success from that single and others on his “Justified” album helped to firmly establish Timberlake as a solo artist. His collaborations with producers The Neptunes (Pharrell Williams and Chad Hugo), Timbaland and Scott Storch burned up the charts and contributed to the soundtrack for the early 2000s.

Years later, in her memoir “The Woman In Me,” Spears dropped a bombshell, writing that she had become pregnant by Timberlake during their relationship and had an abortion.

“It was a surprise, but for me, it wasn’t a tragedy,” she wrote. “I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated.”

Timberlake, she alleged, “definitely wasn’t happy about the pregnancy.”

“He said we weren’t ready to have a baby in our lives, that we were way too young,” she wrote.

Timberlake never directly responded to the content featured in Spears’ memoir about their relationship.

The end of NSYNC

After seven years of making hits, NSYNC stopped performing as a group in the early aughts, but it was a long and loaded goodbye, bye, bye.

The band first went on a hiatus in 2002, the same year Timberlake released his first solo album. At the time, Timberlake downplayed how his desires to go solo may affect the band’s future.

“There’s no reason my solo career and NSYNC can’t coexist in the same universe. NSYNC is in no danger. The break we’re on was a conscious move,” he told the New York Post. “We all wanted to do it, and we were ready to do it. Performing at stadiums every night for 50,000 fans takes a little out of you … The time was right; we were all in the same zone.”

Joey Fatone, Lance Bass, Justin Timberlake, JC Chasez and Chris Kirkpatrick of NSYNC at the VMAs in 2023. (Noam Galai / Getty Images)

Timberlake never permanently returned to the group, who have over the years spoken more about their split. The five have, however, reunited a few times since, once for a surprise performance at the 2013 MTV VMAs and a decade later to present an award.

Fans have been clamoring for new music for years and that intensified after they reunited for the song “Better Place” for the soundtrack of “Trolls Band Together.” Timberlake stoked that desire this year by including another song with his former group, “Paradise,” on his latest album, “Everything I Thought I Was.” He also brought them on stage to perform with him at a show in Los Angeles in March.

Super Bowl wardrobe malfunction

It’s been more than 20 years since Justin Timberlake ripped Janet Jackson’s top and exposed her breast during their Super Bowl XXXVIII halftime show performance, but many Jackson supporters still aren’t over it.

After the incident, hundreds of thousands of complaints flooded into the Federal Communications Commission, CBS (which aired the Super Bowl) was fined and Jackson’s career suffered. Timberlake, then 23, was criticized for not doing more to publicly support Jackson in the aftermath.

The pair denied the wardrobe malfunction was a planned publicity stunt and in her 2022 Lifetime documentary, Jackson said she tried to advise Timberlake after the controversy.

“We talked once, and he said, ‘I don’t know if I should come out and make a statement,’” she said. “I said, ‘Listen, I don’t want any drama for you. They’re aiming all of this at me.’ So I just said if I were you, I wouldn’t say anything.”

The event “was blown way out of proportion,” she added.

“Of course, it was an accident. That should not have happened, but everyone is looking for someone to blame, and that’s got to stop,” Jackson said in the documentary. “Justin and I are very good friends, and we will always be very good friends. We spoke just a few days ago, and he and I have moved on, and it’s time for everyone else to do the same.”

For his part, Timberlake publicly apologized to both Jackson and Spears in 2021 for his “missteps” via a social media post.

“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,” Timberlake wrote. “I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be a part of and grow from.”

Timberlake did not in his statement offer specific examples of the actions for which he felt regret, but his comments came at a time of renewed conversations about both his performance with Jackson and his breakup with Spears. (Spears was in the midst of a high-profile legal battle involving to her conservatorship and had found vocal supporters in the wake of the airing of “Framing Britney Spears,” a documentary examining the singer’s career and the often shameful scrutiny she has faced in the media.)

Films and family

Beyond No. 1 hits like “SexyBack” off his 2006 album “FutureSex/LoveSounds” and “Mirrors” from the “20/20 Experience,” Timberlake found success on the big screen in “The Social Network” and “Bad Teacher.”

He also found love, marrying actor and producer Jessica Biel in 2012. The two are parents of sons, Silas, 9, and Phineas, 3.

Justin Timberlake and Jessica Biel in 2020. (Rodin Eckenroth / Getty Images)

“Love at first sight isn’t limited to the first time you lay eyes on your person. You make me believe that… because every time I look at you, I fall in love bigger and better than I ever could have imagined,” Timberlake wrote of Biel in a Valentine’s Day post shared on Instagram. “Every day I get to share with you reminds me how lucky I am to experience love without limits or conditions. You make me laugh like a child and love with a fierceness that takes me aback.”

Their affectionate relationship has also faced a few hurdles. In 2019, photographs surfaced of Timberlake holding hands in New Orleans with his co-star Alisha Wainwright while the two were filming the drama “Palmer” in the city.

He publicly apologized to Biel in a statement at the time.

“A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my costar,” he wrote. “I drank way too much that night and I regret my behavior. I should have known better.”

He added: “I apologize to my amazing wife and family for putting them through such an embarrassing situation, and I am focused on being the best husband and father I can be. This was not that.”

Five years later, Timberlake may be feeling regret once again.

He has not yet publicly commented on his DWI charge. An attorney for the singer told CNN Timberlake was also cited for running a stop sign and failure to stay in his lane. Timberlake is currently on his “Forget Tomorrow World Tour” and scheduled to perform in Chicago this weekend.