Justin Timberlake’s major scandals over the years: DWI, Nipplegate, Britney Spears drama, more

Since stepping into the spotlight over three decades ago, Justin Timberlake has faced his fair share of controversies.

From being arrested on charges of DWI to Nipplegate, keep scrolling for a list of the singer’s most headline-making scandals.

Britney Spears Drama

Justin Timberlake’s romance with Britney Spears came under the microscope again in 2023 after the pop star released her memoir. Getty Images

Timberlake was 18 when he struck up a romance with pop star Britney Spears.

But after their relationship fizzled out three years later, the singer suggested in his hit song “Cry Me a River” that Spears had cheated on him.

Two decades later, the “Toxic” singer flipped the script on Timberlake when she accused him of cheating on her a “couple” of times in her tell-all memoir, “The Woman In Me.”

Timberlake has dealt with several accusations of infidelity over the years. Getty Images

Janet Jackson Super Bowl Halftime Show

Timberlake sparked backlash again in 2004 after he exposed Janet Jackson’s breast while performing together during the Super Bowl XXXVIII Halftime Show.

Infidelity

Timberlake was arrested on charges of DWI in June 2024. Doug Kuntz

Timberlake allegedly cheated on now-wife Jessica Biel in 2010 with Olivia Munn.

Nine years later, he was spotted getting cozy with “Palmer” co-star Alisha Wainwright at a bar — despite still being married to Biel.

DWI Arrest

In June 2024, Timberlake was arrested on charges of DWI in Sag Harbor, NY. A source told Page Six at the time that the “Trolls” voice actor was pulled over after having dinner with friends at the historic American Hotel.