Rise and fall of Justin Timberlake, from Prince of Pop to purveyor of ‘schlock’

As his comeback single flops, fans are also re-examining his role in the downfalls of Britney Spears and Janet Jackson

Justin Timberlake’s comeback comes amid a changing music and pop culture landscape filled with fans who may not be as forgiving as previous generations. Photo: Getty Images

Gemma White

Feb 17, 2024

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With 10 Grammys, four Emmys and the music media-bestowed title of the “Prince of Pop”, it once seemed unfathomable that Justin Timberlake’s musical crown could slip so far.

A shining star of 1990s and early 2000s pop music, Timberlake, now 43, parlayed his boyband beginnings and relationship with Britney Spears, then the biggest pop star on the planet, into an acclaimed, award-winning solo career.

Somewhere along the line, the culture shifted in ways Timberlake not only failed to anticipate, but also failed to move with.

His past actions and behaviour, particularly in relation to Spears and Janet Jackson, have been put under the microscope by a new generation in a less-forgiving cultural landscape, while his new music became the subject of a vitriolic review that went viral.

Ahead of the March 15 release of his sixth studio album, Everything I Thought It Was, here we chart the rise, decline and ultimate fall of Justin Timberlake…

1992: Early promise

Aged 11, the Tennessee-born star performs Love’s Got a Hold on You by country star Alan Jackson for his appearance on US television talent show Star Search.

Performing under the name Justin Randall, he does not win, but the fame bug bites.

1993-1994: Rising talent

He wins a spot as a Mouseketeer on Disney children’s TV show The All-New Mickey Mouse Club. His fellow cast members include Britney Spears, Christina Aguilera and his future Nsync bandmate JC Chasez.

“If my parents hadn’t got me to those auditions, at some point I would have found a way myself,” Timberlake told The Guardian.

1995-2002: Global fame

Justin Timberlake with his fellow Nsync bandmates Chris Kirkpatrick, Joey Fatone, Lance Bass and JC Chasez, Photo: PA

Along with Chris Kirkpatrick, Joey Fatone, Lance Bass and JC Chasez, Timberlake finds fame with boy band Nsync and they break through with their second album, No Strings Attached, in 2000.

Featuring the monster hit Bye Bye Bye, it wins three American Music Awards and five Billboard Music Awards. The group goes on hiatus in 2002 following their Celebrity Tour.

1999-2002: Ultimate power couple

Justin Timberlake’s fame was given a massive boost thanks to his relationship with Britney Spears. Photo: Getty Images

As Nsync establish themselves, Timberlake receives a priceless publicity boost thanks to his relationship with the biggest pop star in the world, Britney Spears. The pair go public in 1999, elevating Timberlake’s fame far above that of his bandmates.

November 2002: Solo success

Timberlake releases his debut solo album, Justified. Produced by Timbaland and The Neptunes (Pharrell Williams and Chad Hugo), the album is a critical and commercial success. Debuting at number two on the Billboard 200, it spawns four hit singles and wins the Grammy for Best Pop Vocal Album.

In his 2007 book Out of Sync: A Memoir, Bass said he and the band felt blindsided by Timberlake’s solo career, writing: “I felt completely betrayed. It ****** me off that Justin’s life got set up perfectly before he came back to the rest of us.”

November 2002: Winning the public’s sympathy

Cry Me A River, the second track from Justified is released with the video featuring a Spears lookalike.

The song’s lyrics, “You told me you love me / Why did you leave me all alone?” were taken by the media and fans as proof of Spears’s alleged infidelity.

Timberlake tells People: “You get to a point when you’re crying yourself to sleep every night.”

November 2003: Playing the wronged man

Spears’s interview with Diane Sawyer on Primetime helps cement Timberlake’s public persona as the betrayed party.

Sawyer drives Spears to tears with a barrage of questions including: “You broke his heart. You did something that caused him so much pain, so much suffering. What did you do?”

February 2004: Teflon Timberlake

Janet Jackson’s “wardrobe malfunction” during the half-time performance at the Super Bowl saw the star vilified with long-lasting damaging effects on her career, while Timberlake escaped unscathed. Photo: WireImage

Justin emerges unscathed from the Super Bowl half-time show “wardrobe malfunction” which saw him reveal Janet Jackson’s breast live on air.

Jackson’s music and videos are banned across network platforms causing long-lasting damage to her career. She is banned from the Grammys at which Timberlake performs and wins Best Male Pop Vocal Performance.

September 2006: Onwards and upwards

After a foray into film, Timberlake releases his second solo album, the Timbaland-produced FutureSex/LoveSounds which debuts at number one on the Billboard 200.

Three singles, SexyBack, My Love and What Goes Around… Comes Around hit the number one spot.

2010: Acclaimed film role

Justin Timberlake’s portrayal of Napster founder Sean Parker in The Social Network was widely acclaimed. Photo: Columbia Pictures

Timberlake flexes his acting muscles in a critically-acclaimed role as Napster founder Sean Parker the David Fincher-directed film The Social Network.

2013: More Grammys

Timberlake’s fourth album, The 20/20 Experience, becomes the best-selling album of 2013 in the US, with two of the singles, Suit and Tie and Pusher Love Girl, winning Grammys for Best Music Video and Best R&B Song.

February 2018: ‘Musical misstep’

Timberlake’s fifth album, Man of the Woods, confused his fanbase with its pivot from pop to country sounds. Photo: RCA

The star’s fifth studio album, Man of The Woods, is released two days before he headlines the Super Bowl half-time show. Although it hits the number one spot in the US, the album is not a critical success.

Pitchfork pans it as “musically and thematically shallow”. It adds: “Man of the Woods is a misstep large enough to merit relitigating Justin Timberlake’s status as a pop superstar.”

2019: Cheating rumours

A paparazzo image of Timberlake holding hands with his Palmerco-star Alisha Wainwright on a night out in New Orleans makes headlines.

“I apologise 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,” he wrote on Instagram.

January 2021: President’s man

Timberlake and Ant Clemons’s performance of Better Days is broadcast at Joe Biden’s inauguration.

February 2021: Spears documentary reframes Timberlake

The Framing Britney Spears documentary introduces her 2003 interview with Diane Sawyer to a new generation, sparking an outpouring of anger towards Sawyer and Timberlake.

“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,” he writes in a now deleted Instagram post.

October 2023: Spears’s memoir puts him under the microscope

Britney Spears was able to tell her side of the story in her memoir, The Woman in Me. Photo: EPA

In her tell-all book, The Woman in Me, Spears lays bare her relationship with Timberlake, putting out her side of the story, saying she was portrayed as “a harlot who’d broken the heart of America’s golden boy”.

“There’s always more leeway in Hollywood for men than for women,” she writes. “And I see how men are encouraged to talk trash about women in order to become famous and powerful.”

January 2024: Vitriolic viral reviews

Timberlake releases Selfish, his first song in almost six years.

A review by the website Consequence goes viral, stating: “Time and again over the last ten years he has gone into the studio with the most accomplished hitmakers in the world, only to produce a tune about as lively as a dead house plant.”

February 2024: Unrepentant views create uncertain future

Days after Spears publicly apologises for how her book had affected Timberlake, he tells the audience at a concert in New York that he’d “like to take this opportunity to apologise to absolutely ******* nobody.”

His words are met with anger by Spears supporters, who utilise social media to rally fans to push her 2011 song Selfish above Timberlake’s track of the same name in the US iTunes chart.

Timberlake’s sixth album, Everything I Thought I Was, is set for release in March. Time will tell what effect his time spent out of the charts, coupled with the ever-changing tastes of a new generation of music fans will have on pop’s unrepentant prince.