Which artist recorded the hit single "My Prerogative" in 1989?

Bobby Brown recorded the hit single “My Prerogative.”

The song was released in 1988 as the second single from Brown’s album Don’t Be Cruel, but its biggest chart impact continued into 1989. It reached No. 1 on the U.S. Billboard Hot 100 in January 1989 and finished as the year’s No. 2 song on the Hot 100 year-end chart. That release-and-chart timeline explains why the song is often associated with 1989.

“My Prerogative” became one of the defining anthems of new jack swing, blending R&B and soul vocals with hip-hop-influenced beats and crisp electronic production. Teddy Riley helped shape the track’s sound, while Brown helped write it as a response to criticism surrounding his departure from New Edition and his solo career.

The song is frequently confused with Britney Spears’ 2004 cover, which introduced it to a later pop audience. Spears did not originate the song: Brown’s version came first and remains the canonical recording. It was also Brown’s first U.S. Billboard Hot 100 No. 1 as a solo artist.