A look back at Justin Timberlake’s controversies amid DWI arrest

NEW YORK — Justin Timberlake’s drunk driving arrest in the Hamptons this week seems to be the final straw as he waves “Bye Bye Bye” to his golden boy image of yore.

The incident is just the latest in controversy the pop star has found himself in over the past few years, many of which have overshadowed what once appeared an untouchable legacy in pop music.

From reexamining his role in the media’s treatment of women like Britney Spears and Janet Jackson to marital issues and a lukewarm revival of his career, here’s a rundown of the scandals that have marred the “Selfish” singer’s recent years.

DWI arrest

The “Cry Me a River” singer, 43, who is in the midst of his “Forget Tomorrow World Tour,” was arrested early Tuesday after he blew through a stop sign in Sag Harbor, Long Island, blocks from where he’d reportedly been partying at the American Hotel.

Timberlake, who failed multiple field sobriety tests and repeatedly refused a chemical test, was arraigned on a drunk driving charge three days before scheduled shows in Chicago. He is also slated to appear at New York City’s Madison Square Garden on June 25 and June 26.

The ordeal could upend the tour as Timberlake is scheduled to appear in court on July 26, the same day he’s set to perform the first of two consecutive shows in Kraków, Poland.

At the time of publication, none of the shows has been canceled.


This isn’t the first time that Timberlake’s wild ways have proved an issue. In an interview that now appears prescient, the “SexyBack” singer reflected in 2006 on how he was able to party under the radar.

“What I really think is that I’ve never done anything that bad,” the then-25-year-old Timberlake told Observer Music Monthly at the time, per Today. “I don’t show up drunk to functions; the drugs that I do have been in my own private time. … I’m just like everyone else, I get completely plastered, I’ve done my fair share of drugs and I’ve been caught places with my pants down; it’s just I make sure there are no cameras around.”

Britney Spears

The “Stronger” singer, 42, pulled no punches in her October 2023 memoir, “The Woman in Me,” which contained several claims about her three-year relationship with the “Social Network” star from 1999 to 2002.

Spears says she had an abortion, at Timberlake’s encouragement, during the former Mickey Mouse Club stars’ widely publicized romance.

She also accused Timberlake of cheating on her — a transgression she admitted to having reciprocated once. Spears felt the music video for Timberlake’s “Cry Me A River,” which cast an apparent lookalike, encouraged the world to see her as a “harlot who’d broken the heart of America’s golden boy.”

Their split featured heavily in the 2021 FX-Hulu documentary “Framing Britney Spears.”

Janet Jackson

Spears isn’t the only famous lady Timberlake’s been accused of having wronged in the early aughts, a time in which many female celebrities were problematically portrayed.

Until more recently, Timberlake rarely if ever caught flak for his role in the 2004 Super Bowl halftime show, when he ripped part of Janet Jackson’s costume, exposing her breast to the world. Much like his split from Spears, while Jackson, now 58, was thrown under the bus, Timberlake came away not only unscathed but on the precipice of even greater stardom.

In 2021, in the wake of the “Framing Britney Spears” release, Timberlake apologized to both women — in a since-deleted Instagram post — for having “contributed to the problem … and benefited from a system that condones misogyny and racism.”

Jackson revealed in the 2022 TV doc “Janet” that she’d encouraged Timberlake to not “say anything” after the halftime show, noting she didn’t “want any drama for you. They’re aiming all of this at me.”

Marital cracks

In November 2019, Timberlake was photographed getting cozy with “Palmer” co-star Alisha Wainwright, 30. The ordeal caused enough of a publicity storm that Timberlake issued a public apology to wife Jessica Biel for the “strong lapse in judgement,” clarifying that “nothing happened between me and my co-star.”

He blamed that on alcohol as well, noting he “drank way too much that night and I regret my behavior. I should have known better.”

The couple, who already shared then-4-year-old son Silas, welcomed their second son, Phineas, the following summer.

Career slump

After backlash relating to the claims in Spears’ memoir, Timberlake started backing out of scheduled gigs intended to promote his album, “Everything I Thought It Was,” which dropped in March of this year and was his first studio album since 2018’s “Man of the Woods.” At least one of his June “Forget Tomorrow” shows was also canceled without explanation from Ticketmaster.

Dubbed a “long-expected but unfortunately timed return,” Variety called out Timberlake’s “familiar and heavy-handed … and dated” promotional rollout for the album. It debuted. at No. 19 on the Billboard Hot 100 and featured a long-awaited collaboration with his former NSYNC bandmates.

During a one-night engagement at Manhattan’s Irving Plaza in February, Timberlake declared that he was sorry “to absolutely f—ing nobody,” as seen in footage that circulated online. The remark was believed to be a reference to Spears, after the latter apologized if her book “offended any of the people I genuinely care about.”