"My Prerogative" is a song by American singer Bobby Brown from his second studio album Don't Be Cruel (1988). It was released on October 11, 1988 as the second single from the album. After recording sessions for the album were completed, Brown and producer Gene Griffin travelled to New York City, since he felt something was "missing" from the record. "My Prerogative" was written by Brown as a response to the criticism he received for his departure from New Edition. He explained the song was about making decisions in one's life and not caring about other people's judgment. "My Prerogative" is often considered a new jack swing anthem, and contains many elements from Teddy Riley productions due to his involvement as one of the song's session musicians.

The song was positively received by critics and was nominated for a Grammy Award in the category of Best R&B Urban Contemporary Single. It was also commercially successful, reaching number one in Billboard's Hot 100 and Hot R&B/Hip-Hop Songs charts. "My Prerogative" also reached top ten positions in many countries, such as Ireland, New Zealand, the Netherlands, and the United Kingdom. The music video for the song features Brown performing the song on stage with his band and dancers. The song was also performed at most of his concerts, usually as the last song of the set list. On the February 4, 1989 performance at Madison Square Garden, he was joined on stage by many popular rap artists and producers of the time.

"My Prerogative" has been covered and sampled by a number of artists from different genres, including Britney Spears. She released her cover in her first compilation, Greatest Hits: My Prerogative (2004). The cover was produced by Bloodshy & Avant and was noted for aptly referring to Spears's relationship with the media at the time. Although the song only appeared in component charts in the United States, Spears's cover surpassed Brown's version worldwide, peaking at the top of the charts in Finland, Ireland, Italy and Norway and reaching the top ten in another fourteen countries.

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