The last person to be surprised that Justin Timberlake was arrested early Tuesday in connection with his drinking and partying may be Timberlake himself.
Nearly 20 years before a reportedly “wasted” Timberlake was handcuffed by police in the Hamptons and charged with driving while intoxicated, the pop star opened up about his partying, excessive drinking and drug use in an interview with a British magazine, saying that he had used drugs and gotten “plastered” in private but was careful to never be caught.
“What I really think is that I’ve never done anything that bad,” he told the Observer Music Monthly in 2006. “I don’t show up drunk to functions; the drugs that I do have been in my own private time. I’ve never been arrested — though that’s not to say that I won’t.”
Timberlake also admitted that he had gotten into trouble with “women, drugs and debauchery” and said, “like everyone else — I get completely plastered.” He again said he had done his “fair share of drugs” and been “caught in places with my pants down.”
Timberlake added to the magazine, “It’s just that I make sure there are no cameras around.”
A music insider told Page Six Tuesday that Timberlake has had “a real drinking problem” for years.
“It’s not a secret. Everyone knows,” the music insider said. “He has a real drinking problem, a lot of weed — but a major alcohol problem, and he’s been hiding and masking it for years.”
Pop superstars Britney Spears (R) and boyfriend Justin Timberlake (L) talk as they sit courtside at the NBA All-Star Game 10 February 2002 in Philadelphia. (TOM MIHALEK/AFP via Getty Images)
The Daily Mail cited its sources who said that Timberlake’s drinking had escalated in recent months as he tried to cope with backlash, prompted by ex-girlfriend Britney Spears’ revelations about him in her 2023 memoir, “The Woman in Me.”
But if Timberlake managed to hide his drinking problem from the public, the cameras have long captured his other sandals over the years.
In 2002, the former NSYNC singer released a video for his hit song, “Cry Me a River,” which insinuated that Britney Spears cheated on him when they dated from 1999 to 2002.
But in recent years, Spears has had the last word, revealing in her 2023 memoir, “The Woman in Me,” that Timberlake cheated on her with another celebrity and pushed her to get an abortion she didn’t want because, at 19, he felt too young to become a father.
The cameras also captured “Nipplegate” at the Super Bowl in 2004, when a “wardrobe malfunction” led to Timberlake exposing Janet Jackson’s breast while they were performing together at the Halftime Show. Jackson was effectively sent “into exile” while Timberlake was more or less left unscathed, the New York Times said.
More recently, paparazzi cameras caught an apparently inebriated Timberlake in New Orleans in 2019, enjoying PDA, holding hands and reportedly getting flirty with Alisha Wainwright, his female co-star in the movie “Palmer.”
Lead actress in a limited series or movie nominee Jessica Biel and Justin Timberlake arrive for the 70th Emmy Awards at the Microsoft Theatre in Los Angeles, California on September 17, 2018. (VALERIE MACON/AFP via Getty Images)
The photos raised questions about the state of his marriage to actor Jessica Biel and whether the former NSYNC singer was reverting to the behavior that reportedly led to him and Biel, his then-girlfriend, breaking up in 2011. Timberlake also had a high-profile romance with Cameron Diaz before he began dating Biel. Timberlake’s behavior included “rampant affairs with other women,” including a widely reported “fling” with actress Olivia Munn in 2010, Us Weekly reported at the time. But Timberlake and Biel eventually reconciled, marrying in 2012 and becoming parents to a son, Silas, in 2015.
Shortly after the New Orleans incident, Timberlake apologized for his “lapse of judgement” and said he “drank way too much that night,” while insisting that nothing happened between him and Wainwright.
Two months after this incident, Timberlake and Biel’s relationship remained strained, with Biel reportedly “still upset,” a source told Us Weekly at the time. But Timberlake and Biel again worked things out, stayed together and welcomed their second son, Phineas, in 2020.
Now, the “SexyBack” singer has become embroiled in scandal once again, with his arrest in Sag Harbor, after he left a hotel where he had dined and “partied” with “a bunch of friends,” according to TMZ, Page Six and other news outlets.
Witnesses told The New York Post that Timberlake was “wasted” at the American Hotel in Sag Harbor, where he grabbed someone else’s drink when the person went to the bathroom and downed it.
It’s also been reported by TMZ that police body-cam cameras were present at Timberlake’s arrest, which took place after he failed a field sobriety test.
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TMZ reported that Timberlake left the American Hotel around 12:30 a.m. He was following friends back to their home in his own vehicle, a gray BMW SUV. About a half mile from the hotel, police spotted him run a stop sign and followed him, observing him swerve in an out of his traffic lane for another half mile, law enforcement sources told TMZ.
After police pulled Timberlake over, he told the officer he only had one martini at the hotel, TMZ reported. But a report of the arrest said that the officer noticed signs of intoxication, including bloodshot and glassy eyes, slowed speech and the odor of alcohol emanating from his breath, TMZ reported. Timberlake also performed “poorly” on field sobriety tests.
Page Six reported that the officer who pulled Timberlake over “was so young that he didn’t even know” who the 10-time Grammy winner was. A source also told Page Six that “Justin said under his breath, ‘This is going to ruin the tour.’”
When the officer asked, “What tour?” Timberlake replied, “The world tour.”
Timberlake is currently on his “Forget Tomorrow” tour, which features hits from his career, as well as from his new album, “Everything I Thought It Was.” He is scheduled to perform in Chicago Friday and Saturday night, then return to New York for performances at Madison Square Garden next week.
TMZ said the police report doesn’t mention that Timberlake’s friends tried to intervene on his behalf at the traffic stop, but both TMZ and Page Six reported that the friends asked the officer “to cut him a break.”
Otherwise, Timberlake was polite and “didn’t show any entitlement at all,” a source told Page Six. He did refuse to take a breathalyzer test, but that “is his right,” the source said.
The “SexyBack” singer was arraigned on Tuesday morning and released from custody on his own recognizance.
Biel also has been in New York, the New York Post reported. On Monday, the day before her husband’s arrest, the “7th Heaven” star was spotted in New York City’s Central Park, filming a scene from her upcoming Amazon Prime series, “The Better Sister.” And, on Sunday, she posted a Father’s Day tribute to him on Instagram.
Along with a photo of him kissing her cheek, Biel wrote, “You’re so many things to so many people. But to us you are THE ROCK. The rock we climb on, we lean against. The rock that shades us from the sun. And when we recline on you, as we always do, hopefully our butts will keep you eternally grounded and warm.”
“We LOVE YOU,” she added with a heart emoji.
