"My Prerogative" is a song by American singer Bobby Brown from his second studio album, Don't Be Cruel (1988). It was released in 1988, as the second single from the album. After recording sessions were completed, Brown and producer Gene Griffin traveled 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 firing 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 as one of the first major songs in the new jack swing genre.

The song was positively received by critics and was nominated for a Soul Train Music 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 in some European countries, peaking at the top of the charts in Finland, Ireland, Italy and Norway and reaching the top ten in another fourteen countries.

Brown had already completed recording sessions for Don't Be Cruel in Los Angeles, California, but felt something was missing in the record. He said, "I felt my album was lacking a strong, aggressive song and I thought, 'Where better than New York to come up with it'". He traveled to New York, met with Teddy Riley - who presented him with the initial beat. "My Prerogative" was written and co-produced by Brown, Timmy Gatling, Aaron Hall, and Gene Griffin. It was recorded at Axis Studios and mixed at Soundworks, in New York. The track was mastered at Future Disc Systems in Hollywood, California. During an interview with The Hour on March 17, 1989, Brown explained the theme behind the song, saying, "A lot of things had been said about Bobby Brown, why was he doing this [a solo career]. It's my way of expressing to people it's your prerogative to do as you want, but make sure what you do is the right thing".

A CD single of remixes by Joe T. Vannelli was released on October 13, 1995, reaching number 17 in the UK Singles Chart. The radio edit from this was included on Brown's 1995 remix album, Two Can Play That Game.

"My Prerogative" is considered a new jack swing anthem, that merges hip hop beats with elements of synthpop and soul. It features a triplet swing in the sixteenth note, as included in many of Riley's productions. Jake Brown said in his book Your body's calling me: music, love, sex & money (2003), that like most new jack swing songs from the late 1980s, it was composed by "punchy, street-savvy beats, with sexually energetic melodies and poppy choruses". The bassline of the track was described by Cam'Ron Davis of CMJ New Music Monthly as "truly sinister". According to the sheet music published at Musicnotes.com by EMI Music Publishing, the song is composed in the key of A minor, with a tempo of 120 beats per minute. Brown's vocal range spans from the high-note of C₄ to A₅.

Barry Michael Cooper of Spin said "My Prerogative" "sounds like gin-drenched, Roaring Twenties swing". Arion Berger of Rolling Stone called it "a grumpy and undeniably adult dance hit". "My Prerogative" was nominated for at the 3rd Soul Train Music Awards in the category of Best R&B Urban Contemporary Single by a Male, but lost to Michael Jackson's "Man in the Mirror". The following year, Spin listed the song at number 72 on the "100 Greatest Singles of All Time" list. It ranked at number 98 on VH1's "100 Greatest Songs of the 80's". The track is often referred to as Brown's signature song.

"My Prerogative" debuted on the U.S. Billboard Hot 100 during the week of October 22, 1988, at number 78. The following week, it jumped 17 positions to number 61, and the following week, it climbed another 16 positions to number 45. It entered the top 40 during its fourth week (number 33 on November 12, 1988), and on January 14, 1989, it peaked at the top position of the chart. "My Prerogative" ultimately spent 24 weeks on the Hot 100, 15 of which were in the top 40. The song also peaked at number one in Hot Black Singles (during the weeks of October 15 and 22, 1988), and at number seven on the Dance Club Play chart. It was certified gold by the Recording Industry Association of America (RIAA) for sales over 500,000 copies. In Canada, the song debuted on the RPM 100 Singles at position 98, on the issue dated December 23, 1989. In the United Kingdom, "My Prerogative" debuted at number 87 on December 10, 1988. On February 18, 1989, the song peaked at number six and stayed in the position for two weeks. Following the release of the remixes single on October 14, 1995, "My Prerogative" re-entered the UK charts at number 17, and stayed on the chart for two weeks. By October 17, 2015, it had sold 275,000 units in the country. Across Europe, the song reached the top ten in Ireland and the Netherlands, and the top 20 in Germany and Sweden. In Australia and New Zealand, the track peaked at number 40 and number three, respectively.