The former Wham! frontman made a complete career 180 when he left the pop group for a solo career that was more soul and R&B than it was teenybopper. Michael died over Christmas at the age of 53. Here’s a look back at some notable songs and moments from his 35-year career.

• Michael’s first solo single after the dissolution of Wham! was the soulful, risqué “I Want Your Sex.” Far from the bubblegum pop of Wham!, it was so frank in its discussion of sexuality that BBC Radio would only play it after 9 p.m., while many American radio stations didn’t play it all. But maybe there’s no such thing as bad publicity: “I Want Your Sex went to #3 on the British pop chart and #2 on the American pop chart.

• Michael first began writing the Wham! hit “Careless Whisper” in 1981, when he was just 17 years old. His Wham! cohort Andrew Ridgeley contributed over the next three years, and when it was released in 1984, it became the biggest hit Wham! would ever have, hitting #1 in the U.S., U.K., Canada, South Africa, Switzerland, Ireland, Italy, Japan, Australia, and the Netherlands. “Careless Whisper” wound up being the top single for the entirety of 1985 in the U.S., where it was released credited to “Wham! Featuring George Michael.” An explicit move toward a solo career for Michael, Wham! broke up not too long after.

• Why is “A Different Corner” a historic song? The song from Michael’s first solo album Faith is a true solo effort. It’s the first time a singer ever hit #1 with a song that he wrote, arranged, produced, song on, and played all the instruments on.

• In 1990, Michael released Listen Without Prejudice, Vol. 1. Despite selling millions of copies, there was never a Listen Without Prejudice, Vol. 2. Why? Michael’s relationship with his label, Sony, soured shorty after the release of Vol. 1. Michael had tired of the pop star life, and wouldn’t do the kinds of things Sony wanted him to do to promote the album, like appearing in music videos. He didn’t appear in the one for the first single “Praying For Time,” nor the follow-up, “Freedom ’90.”

• In early 1998, Michael was arrested in a Beverly Hills park’s restroom when he tried to solicit an undercover police officer for a “lewd act.” He was forced to publicly declare that he was homosexual. But rather than embark on the usual celebrity scandal route of public apologies on talk shows, Michael made light of the event by recording the single “Outside.” He makes fun of himself and the incident, especially in the video, in which a park’s restroom magically transforms into a disco.