"My Prerogative" is a song by American recording artist Bobby Brown from his second solo studio album, Don't Be Cruel. It was released on October 11, 1998 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 your life and not caring about other people's judgement. "My Prerogative" is often considered a new jack swing anthem, and contains many elements from Teddy Riley productions.

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 is 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, most notably by Britney Spears. She released her cover in her similarly titled 2004 greatest hits compilation. The cover was produced by Bloodshy & Avant and was noted for aptly referring to Spears's relationship with the media at the time. It received mostly unfavorable reviews from critics, with one reviewer calling it "unnecessary". 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. The music video, directed by Jake Nava, portrays Spears arriving at a Hollywood Hills manor in which a party is taking place. In the end, it is revealed that the party is actually Spears's wedding.

Brown had already completed recording sessions for Don't Be Cruelin 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 to New York to come up with it'". He travelled to the city with producer Gene Griffin. "My Prerogative" was written and co-produced by Brown, Griffin and Teddy Riley. 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 Houron 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".

"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 1980's, 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 Monthlyas "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 C to A.

Barry Michael Cooper of Spinsaid "My Prerogative" "sounds like gin-drenched, Roaring Twenties swing". Arion Berger of Rolling Stonecalled it "a grumpy and undeniably adult dance hit". "My Prerogative" was nominated for at the 30th Grammy 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, Spinlisted the song at number seventy-two on the "100 Greatest Singles of All Time" list. It ranked at number ninety-eight 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. BillboardHot 100 during the week of October 29, 1988 at number sixty-one. The following week, it climbed sixteen positions to number forty-five. On January 14, 1989, it peaked at the top position of the chart. The song also peaked at number one in Hot R&B/Hip-Hop Songs and at number seven in Hot Dance Club Songs. 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 RPMSingles Chart at position ninety-eight, on the issue dated December 23, 1989. In the United Kingdom, "My Prerogative" debuted at number eighty-seven on December 10, 1998. On February 18, 1989, the song peaked at number six and stayed in the position for two weeks. Across Europe, the song reached the top ten in Ireland and the Netherlands, and the top twenty in Germany and Sweden. In Australia and New Zealand, the track peaked at number forty and number three, respectively.

The music video for "My Prerogative" was directed by Alek Keshishian. It begins with Brown driving a car while his musicians start to perform the song on a stage. Shortly after, he descends to the stage in an elevator, wearing a black jumpsuit and a headset. He dances flanked by two women, one of them playing a keytar. J. D. Considine of Rolling Stonewrote in the review of Bobby(1992), "As anyone who saw him swagger through the videos for 'My Prerogative' and 'Every Little Step' can attest, Brown had a phenomenal ability to convey a sense of street toughness that was utterly without malice or menace, making him credible and likable". The music video was nominated at the 1989 MTV Video Music Awards for Best Stage Performance in a Video, but lost to the music video of Living Colour's "Cult of Personality". It also charted at number nine on RPMvideo chart on July 21, 1990.

"My Prerogative" was performed during his tour in promotion for Don't Be Cruelas the last song of the night. Brown usually performed it wearing a black outfit, flanked with two male dancers wearing white clothes. On the February 4, 1989 show at Madison Square Garden in New York City, wore a red boxing robe with the words "King of the Stage" printed in the back. During the performance, Joseph Simmons of Run-DMC, LL Cool J and Heavy D joined him onstage and freestyle rapped. Eric B., KRS-One, L. A. Reid, Babyface and Teddy Riley also joined him onstage, with the latter performing a keyboard solo. Peter Watrous of The New York Timescommented that, "The communal scene on stage mirrored the feeling in the audience; everybody seemed aware that this was a generation that had rewritten the rules of pop entertainment, and was justifiably proud of its achievement". Brown also performed the song at the 1997 Home Again Tour with New Edition, during the second portion of the show in which he performed hits from his solo career. On November 10, 2005, he performed the song for the first time in eight years at a concert at House of Blues in Atlantic City. He wore a white suit and matching hat, and sang it as the last song of the evening. On January 17, 2006, he performed it at a New Edition show in Atlantic City's Trump Taj Mahal. During the performance, he tore open his orange dress shirt, singing bare-chested with a tie and a fur coat on. Brown also performed the song during his 2007 July shows in Australia.

"My Prerogative" was sampled and covered by many artists from different genres. It was sampled in Nice & Smooth's "O-o-h Child" (1989), Public Enemy's "Pollywanacraka" (1990), Nice & Smooth's "Hip Hop Junkies" (1991) and LL Cool J's "Doin It" (1995). J.D. Considine of Rolling Stonenoted that the hook of Brown's 1992 single "Humpin' Around" from Bobby, "bears a more than passing resemblance to the synth part from 'My Prerogative'". According to Entertainment Weekly, American R&B group U.N.V. sampled the melody for their 1993 single "Something's Goin' On". Jamaican reggae singer Beenie Man covered "My Prerogative" for his 1998 studio album Many Moods of Moses. American singer Rod Michael covered the song for his 2004 studio album, The Next Episode. English rock band Selfish Cunt also covered the song for their 2004 studio album No Wicked Heart Shall Prosper, changing the name to "Bobby". On July 2007, American basketball player LeBron James covered "My Prerogative" at the 15th ESPY Awards at the Kodak Theatre in Hollywood, California, wearing a wig and Hammer pants. Vibenamed the performance one of the "worst of the worst live performances of the year". Anoop Desai, contestant of the eight season of American Idol, covered the song for his wildcard round performance. It earned him the last spot in the finals, marking the first time the show ever had thirteen contestants. Desai also performed the song during the American Idols LIVE! Tour 2009. Graeme McRanor of The Vancouver Sunsaid in the concert review that "My Prerogative" "really shouldn't be covered by any artist, ever again". On July 31, 2009, American hip hop group The Pharcyde covered the song at the All Points West Music & Arts Festival in Jersey City. The song was also featured on the films Love & Basketball(2000), Wild Hogs(2007) and Sex Drive(2008).

In 2004, Spears recorded a cover of "My Prerogative" with Swedish production team Bloodshy & Avant, who produced her single "Toxic" from her fourth studio album, In the Zone(2003). Bloodshy & Avant recorded the song at Murlyn Studios in Stockholm, Sweden. Spears recorded the vocals at Teldex Studios in Berlin, Germany. On August 13, 2004, Spears's label Jive Records announced through a press release that she had covered the song and was planning to release it on her first greatest hits compilation, titled Greatest Hits: My Prerogative. The song was set to premiere on radio stations on September 14, 2004, however, it leaked in the Real Tapemasters Inc.'s mixtape The Future of R&Bon September 10, 2004. Spears's cover of "My Prerogative" is musically different from its original version, with the bass and new jack swing sound replaced with synthesizers and elements typical of Bloodshy & Avant productions. It was noted by Christy Lemire of msnbc.com that the cover also contains elements of Bollywood music. At the beginning of the song, Spears says in a breathy voice the lines "People can take everything away from you / But they can never take away your truth / But the question is, can you handle mine?". The rest of the lyrics do not deviate much from the original version, instead they are changed to fit a woman's perspective. Jennifer Vineyard of MTV commented the cover could be interpreted as a statement on Spears's life and the media reaction to some of her decisions at the time, including her engagement to American dancer Kevin Federline.

Stephen Thomas Erlewine of Allmusic called the cover "a useless remake, which seems to exist solely for its video". Spence D. of IGN said that the lyrics fit perfectly with Spears's relationship with the media at the time. He also added, "As for her interpretation, it's an interesting chameleonic diversion that comes off like a mash-up between vintage Prince-styled production, Cameo swagger, and Madonna sultriness, but never seems to capture the gloss and glory of any of the aforementioned influences". Christy Lemire of msnbc.com called it "utterly unnecessary". Louis Pattison of the New Musical Expresscommented that "judging by the fuck-you sentiments" of the cover, Spears liked to play the role of "[the] pop brat careering off the rails". Sarah Hepola of Salon.com wrote in an article about contemporary teen idols that the cover "became an anthem for teen-idol rebellion". American director Quentin Tarantino included the song in a playlist that inspired him during production of his 2009 film Inglourious Basterds.

In the United States, "My Prerogative" charted in Billboard's Top 40 Tracks and Top 40 Mainstream at number twenty-two and thirty-four, respectively. On November 15, 2004, the song debuted at the Australian Singles Chart at number seven. The same week, it debuted at number seventeen in New Zealand. On November 7, 2004, the song debuted at number three in the United Kingdom, during a competitive week of new releases, only surpassed by Eminem's "Just Lose It" and Destiny's Child's "Lose My Breath". The song also reached success throughout Europe, peaking at number one in Finland, Ireland, Italy and Norway, number two in Spain and number three in Belgium (Flanders and Wallonia), Denmark and Germany. It also reached top ten positions in Austria, Czech Republic, Sweden, Switzerland and the Netherlands.

The music video for "My Prerogative" was filmed in August 2004 at The Paramour Mansion in Silver Lake, Los Angeles, California and was directed by Jake Nava. According to Spears's mother Lynne, the video was "about capturing gorgeous close-ups and very subtle movement" since Spears could not do any choreography due to her knee injury at the "Outrageous" music video shoot. She also described the video as "[having] an element of old Hollywood glamour and mystery". The music video begins with Spears driving a Porsche 928 at high speed in the Hollywood Hills. She crashes through a fence and lands into a pool inside a manor where a party is taking place. She emerges from the water and crawls in top of the car to sing the first verse. Spears's brother Bryan makes a cameo in these scenes. After she leaves the pool, she enters the manor and passes couples making out around her. She appears in a stainless steel kitchen, where a maid cuts the straps of her black wet dress. In the next scene, she walks into a study in which her husband at the time, Kevin Federline, is smoking and watching a black-and-white video of Spears on a projection screen. According to Jennifer Vineyard from MTV, the clip had the style of pornographic films from the 1940's and 1950's. Rolling Stonein their article "Britney Spears: The Complete Video Guide", compared it to Madonna's performances of her 1984 single "Like a Virgin". She then entered a dressing room with mirrors, wearing lingerie, high heels, stockings and a short fur jacket. She proceeds to a bedroom, in which a black dress is laid out on the comforter. She puts on the new dress and the camera cuts to the party outside where people gathered waiting. During the song's bridge, it is revealed that the party is actually Spears's wedding, as she starts walking towards the aisle and Federline waits next to a priest. The video ends with a shot of the black-and-white video and Spears looking into the camera. The footage was released as an alternate version of the music video in the 2004 DVD Greatest Hits: My Prerogative.