Justin Timberlake's Most Shocking Controversies: From 'Nipplegate' to Coerced Abortion

A Rundown of Justin Timberlake's Major Controversies 

Justin Timberlake has had his fair share of controversies. The most recent scandal to do the rounds concerns his arrest for driving while intoxicated (DWI). From the infamous ‘Nipplegate’ to the more recent shocking revelations in his former partner, Britney Spears' memoir, life lately has been tough for Timberlake. For each controversy, he also went through public apologies and media backlash. Here are a few other incidents that put the pop star in the spotlight for all the wrong reasons.

1. The Spears Abortion Controversy

In her memoir, The Woman in Me, Spears disclosed that during her relationship with Timberlake, she became pregnant with his child but decided to have an abortion. As reported by People magazine, she penned, “I always expected us to have a family together one day. This would just be much earlier than I’d anticipated. But Justin 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 added, "If it had been left up to me alone, I never would have done it. And yet Justin was so sure he didn’t want to be a father."

2. Infidelity Rumors

Timberlake and Spears met in 1999 and dated for two years before calling it quits in 2002. Following their breakup, Timberlake went on to release a track Cry Me River, which many believed was about Spears's infidelity. The music video had a look-alike of Spears playing out a character who cheats. Years later, in her memoir, Spears alleged that Timberlake was the one who cheated on multiple occasions, as per Page Six. She also disclosed that he ended their relationship via a text message.

3. Journey With NSYNC

During the 1990s and early 2000s, NSYNC captivated audiences and dominated the music charts before taking a break in 2002. The group officially parted ways in April of that year when Timberlake decided to go solo. As reported by Hello! magazine, he said, "It started as a fun snowball fight that was becoming an avalanche. And, also, I was growing out of it. I felt like I cared more about the music than some of the other people in the group. And I felt like I had other music I wanted to make and that I needed to follow my heart."

4. Nipplegate Accident

During the halftime show of the 2004 Super Bowl, Janet Jackson performed with Timberlake joining her on the stage. In the middle of their performance, Timberlake ripped off a portion of her outfit, which revealed her right breast with a nipple ring, according to Fox News. Following backlash online, Timberlake offered an apology stating that what happened was ‘unrehearsed’ and ‘unintentional.’ In 2021, Timberlake issued another apology for not speaking out after the event. This led to huge debates in Congress as nudity on television during Superbowl was prohibited.

5. Jessica Biel Cheating

Timberlake and Jessica Biel have been involved in a fairly dramatic on-and-off relationship over the years. Specifically, in October 2010, there were reports that Timberlake cheated on Biel with Olivia Munn. As reported by the New York Post, a source said the two had a three-day affair after meeting at a MySpace party. The allegations however were refuted by Timberlake’s representative. Timberlake and Biel eventually set their differences aside and got married in 2012. The couple has since been blessed with two kids, Silas and Phineas.

6. Alisha Wainwright Scandal

In November 2019, Timberlake was photographed holding hands with his Palmer co-star, Alisha Wainwright, at a bar in New Orleans. The following month, Timberlake issued a public apology for the incident. As reported by Page Six, he said, “I stay away from gossip as much as I can. But for my family, I feel it is important to address recent rumors that are hurting the people I love.” He admitted, “I drank way too much that night and I regret my behavior. I should have known better. This is not the example I want to set for my son."

7. NSYNC Credit Drama

NSYNC’s first new song in over two long decades was Better Place, which was released in September last year. It came up as part of the soundtrack for Timberlake’s animated movie, titled Trolls Band Together. However, observant fans soon pointed out that the song was listed as "NSYNC featuring Justin Timberlake". This raised questions about why Timberlake was given special treatment. However, none of the band members chose to weigh in on the credit controversy, as reported by Us Weekly.

8. Arrested for Driving While Intoxicated

Timberlake was recently arrested for drunk driving in Long Island, New York. A police statement read, "On June 18, 2024, at 12:37 AM, Justin R. Timberlake, age 43, of Tennessee, was observed operating a 2025 BMW southbound on Madison Street, failing to stop at a duly posted stop sign and failing to maintain his lane of travel...and upon investigation, it was determined that Mr. Timberlake was operating his vehicle in an intoxicated condition." As reported by People magazine, he was held in custody overnight for morning arraignment.