Justin Timberlake's highs and lows: from his NSYNC and solo stardom to Britney Spears controversy and DWI arrest

In 1993, Justin first achieved fame when he joined The Mickey Mouse Club as one of their Mouseketeers, impressing kids and parents with his smooth voice and equally impressive moves.

From 1993-94, he worked on the series alongside future bandmate JC Chasez, Christina Aguilera, Ryan Gosling, Keri Russell, and none other than…

In 1999, Justin began dating Britney Spears, and for nearly three years, they were the entertainment power couple (hello, double denim MTV VMAs outfits). They abruptly split up in 2002.

At the time, Britney was painted as the one who strayed, but in more recent years, his language toward her was deemed misogynistic. In her 2023 memoir The Woman in Me, Britney laid many aspects of their relationship bare, claiming that he often cheated and allegedly made her get an abortion in 2000 when she became pregnant with his baby.

READ: Britney Spears' biggest memoir bombshells: Justin Timberlake pregnancy, head-shaving incident and more

Following his turn as a Mouseketeer, Justin recruited JC and joined Chris Kirkpatrick, Joey Fatone, and Lance Bass to form NSYNC, which was an instant phenomenon.

The group sold more than 70 million records worldwide, one of the best-selling boy bands of all time, and through ups and downs, they remain close to this day. However, they went on hiatus in 2002, with Justin focusing on solo endeavors after quickly becoming the group's breakout star.

RELATED: Why did NSYNC split up? Real reason explored

With the release of his 2002 debut album Justified, Justin cemented himself as one of the biggest pop and R&B stars of the 2000s, building on that with 2006's FutureSex/LoveSounds. Both albums were global hits, aided also by production from the likes of Timbaland and The Neptunes.

Songs like "Cry Me a River," "Rock Your Body," "SexyBack," "My Love," "What Goes Around…Comes Around," "Summer Love," and "Give It To Me" remain popular to this day and were huge successes upon release, earning him six Grammys.

At the height of his rise, Justin joined Janet Jackson during her Super Bowl XXXVIII performance, and inadvertently caused a (now infamous) wardrobe malfunction. While both parties apologized, Justin's career continued to blossom, and Janet was effectively blacklisted.

In the years since, the tides have shifted in Janet's favor, resulting in Justin issuing a lengthy apology once again to Janet (and Britney) in 2021 for not letting them take the fall after their respective controversies, which received mixed reception.

MORE: Britney Spears shares very surprising message about ex Justin Timberlake amid unexpected musical battle

After dabbling with acting work throughout the early 2000s, Justin took a break from music to focus on his screen career soon after recording the 2008 smash "4 Minutes" with Madonna.

While he did appear in flops like The Love Guru in 2008, he starred in several commercial and critical successes between 2010-2013, most notably The Social Network (2010), Bad Teacher, Friends with Benefits (both 2011), and Inside Llewyn Davis (2013).

In 2007, Justin began dating actress Jesscia Biel, and the couple tied the knot in 2012. They're the parents of sons Silas, nine, and Phineas, four. However, their marriage has experienced difficulties. 

SEE: Justin Timberlake and Jessica Biel's private split nine months before surprise engagement

Most notable would be in 2019, when he was photographed holding hands with Palmer co-star Alisha Wainwright. He issued an apology to Jessica and his family soon after, although their relationship came under scrutiny once again in 2023 when Britney's The Woman in Me was released.

In 2013, he returned to music with The 20/20 Experience, with his revamped polished image earning him considerable acclaim and success. The 20/20 Experience became the best selling album of the year, generating hits like "Suit & Tie" and "Mirrors," winning him three more Grammys.

His success continued 2018's Man of the Woods and his 2017 contribution to the soundtrack of Trolls, "Can't Stop the Feeling," which was a worldwide sensation and even earned him an Oscar nomination. His latest release, March's Everything I Thought It Was, however, was his first album since Justified to not go number one.

In 2018, Justin returned to the Super Bowl to headline the Super Bowl LII Halftime Show amid backlash for allowing him to return while Janet hadn't been given a second chance.

The show itself received a mixed response, with praise going to his vocals and dance moves, but criticism for playing it "too safe" and effectively turning in a performance that was deemed "boring."

And we arrive at the present day, with Justin's DWI arrest. The singer quickly went viral once news broke of the conviction, especially for his mugshot and his apparent response to the apprehending officers.

MORE: Justin Timberlake's lawyer breaks silence following singer's DWI arrest

While it's unclear how this will affect his ongoing The Forget Tomorrow World Tour, Justin is slated to return to the stage in Chicago on June 21, so stay tuned on that front!