John Mayer has made headlines recently for a seemingly tame series of events: voicing support for Britney Spears, joining TikTok, and performing at the 2021 Grammy Awards.

However, while Mayer’s current persona may not seem contentious, it’s marred by a series of controversies throughout his career.

The “New Light” singer, who burst onto the music scene with 2001’s “Room for Squares,” quickly became known for giving “raw” interviews and being “in love with the sound of his own voice.” His rap sheet includes troubling anecdotes from ex-girlfriends, which suggest a pattern of toxic behavior, several racist remarks, and accusations of cultural appropriation.

Insider compiled a timeline of Mayer’s offensive comments and backlash he’s received over the years.

2006: Mayer made lewd comments about Jennifer Love Hewitt during a live-comedy routine
Mayer’s first brush with notoriety came during a surprise appearance at The Laugh Factory in Los Angeles.

His stand-up set included a pointed jab at his ex-girlfriend, Jennifer Love Hewitt, whom he dated in 2002. It was widely assumed that Mayer’s hit song “Your Body Is a Wonderland” was inspired by the “Ghost Whisperer” actor.