Bobby Brown asserts his independence on this song, where he makes it clear that he doesn't care what other people think about him. Brown left the very successful group New Edition in 1985 so he could pursue a solo career. His first solo album, released in 1986, contained the #1 R&B hit "Girfriend," but failed to expand his audience. On "My Prerogative," he takes on the folks that accuse him of being crazy for leaving the band and also addresses charges of philandering, explaining that he makes no apologies for his liaisons with the ladies.
The Don't Be Cruel album silenced any critics who questioned his viability as a solo artist: the album was the US top-seller in 1989 and produced a #1 hit with "My Prerogative."
This song helped Brown establish an image as a bad boy and an outcast. He really wasn't all that scandalous at the time, and his music had been far from controversial - his first solo album pretty much cloned his New Edition sound. He was just 19 when the Don't Be Cruel album was released, and considering his fame and fortune, was reasonably grounded - he kept a tight circle of friends, was close with his family, and ended his concerts with a prayer.
Much of the judgment toward Brown was based on his upbringing, which was rough. He grew up in housing projects in the Roxbury section of Boston; when he was 10, he got caught in crossfire from a gang incident and was shot in the knee. A year later his friend Jimbo Flint was stabbed to death at a party. Brown did some shoplifting and got into some trouble, but he was also very ambitious, forming New Edition when he was 12 and then leaving the group when he felt he was being exploited.
When Brown started dating Whitney Houston in 1989, however, this bad-boy image was played up by the media, which promoted a narrative of the wild-and-crazy Brown corrupting the innocent Houston. He was certainly in the news before "My Prerogative," but he soon became tinder for the tabloids as part of the most famous couple in music.
The writing credits on this song list Brown, his producer Gene Griffin, and the songwriter/producer Teddy Riley (you can hear Brown give him a shout: "I made this money, you didn't - right Ted?"). For a long time, Riley's name was left off the credits, although Brown acknowledged that he wrote the song. Riley says that he wrote the song with Aaron Hall, who was in the group Guy with Riley. "When we came up with that song, we thought of it for Bobby Brown because of all the situations he's been in - people saying he's on drugs," Riley said in the Billboard Book of #1 R&B Hits. "I feel it's Bobby's prerogative to do what he wants to do."
In America, this was the second single released from the Don't Be Cruel album, following the title track. It made #1 on the R&B chart in October 1988, and three months later topped the Hot 100.
It also broke Brown in the UK, earning him his first Top 40 there when the song reached #6.
Alek Keshishian directed the video, which shows Brown performing the song in a concert setting. The clip showcased Brown's dance moves, a strategy Keshishian further employed on his next video, for "Every Little Step."
Britney Spears covered this song in 2004, including it as one of three new songs on her album Greatest Hits: My Prerogative. Her version, which was released as a single accompanied by a big-budget video directed by Jake Nava, went to just #101 in the US but made #3 UK and #1 in Ireland.