When George Michael wrote Club Tropicana with fellow Wham! member Andrew Ridgeley, he wouldn’t have guessed he’d shoot to fame at the age of 18. While the singer sold millions of records during his career, he was also plagued by personal strife. George famously said in an interview, “I realised early on that being on the road to pop stardom was not going to bring me happiness, but I couldn’t get off.” Aside from battling the stigma related to homosexuality and AIDS, the star also struggled with substance abuse. Here are the most controversial moments of the pop legend’s life.

Bathroom incident: In 1998, George Michael was arrested for a “lewd act” in a public bathroom in California, which has never been elaborated on, but was assumed to be homosexual in nature. While many had already guessed that the star was gay, the arrest confirmed the fact.

Coming out interview: The high-profile arrest forced the singer to come out as gay. In a candid interview, George announced that he was in a relationship with Kenny Goss, saying, “We are not monogamous. This is not an uncommon state of affairs in long-term gay relationships. It is not open in any emotional sense, just physical. That’s the way we choose to live.”

Releasing ‘I Want Your Sex’: Breaking away from his clean-cut image, George released the controversial I Want Your Sex song in 1987. It was the first song to feature the word ‘sex’ in the title and was therefore banned by the BBC and several radio stations in the US.

Watch the video here:

Shoot the Dog video: At the height of the Iraq War, George Michael released the 2004 single Shoot The Dog. The political satire showed cartoon versions of then US President George Bush in bed with the then UK Prime Minister Tony Blair. The song received flak to the point that George was forced to leave the US.

Check out the video here:

Drug arrests: In 2007, Michael was arrested for falling asleep at the wheel of a car in the middle of London traffic. Although he temporarily lost his license, in 2010, he was in a drug-related car accident again and had to serve an eight-month prison term.