[1] 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.

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.

The cover was produced by Bloodshy & Avant and was noted for aptly referring to Spears's relationship with the media at the time.

"My Prerogative" is considered a new jack swing anthem, that merges hip hop beats with elements of synthpop and soul.

[9] 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".

[14] "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".

[28] It begins with Brown driving a car while his musicians start to perform the song on stage in front of a large crowd.

[11] J. D. Considine of Rolling Stone wrote 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".

[32] On the February 4, 1989, show at Madison Square Garden in New York City, Brown wore a red boxing robe with the words "King of the Stage" printed on the back.

Peter Watrous of The New York Times commented 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".

In 2004, American singer Britney 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).

Spears recorded the vocals at Teldex Studios in Berlin, Germany during the European leg of her The Onyx Hotel Tour in 2004.

[52] Jennifer Vineyard of MTV commented the cover could be interpreted as a statement on Spears' life and the media reaction to some of her decisions at the time, including her engagement to American dancer Kevin Federline.

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".

[55] Louis Pattison of the New Musical Express commented that "judging by the fuck-you sentiments" of the cover, Spears liked to play the role of "[the] pop brat careering off the rails".

[58] Sarah Hepola of Salon wrote in an article about contemporary teen idols that the cover "became an anthem for teen-idol rebellion".

[3] The music video for "My Prerogative" was filmed in August 2004 at The Paramour Mansion in Silver Lake, Los Angeles and was directed by Jake Nava.

In the next scene, she walks into a study in which her then-fiancé, Kevin Federline, is smoking and watching a black-and-white video of Spears on a projection screen.

[72] Rolling Stone in their article "Britney Spears: The Complete Video Guide", compared it to Madonna's performances of her 1984 single "Like a Virgin".

[73] She then entered a dressing room with mirrors, wearing lingerie, high heels, stockings and a short fur jacket.

[72] During the song's bridge, it is revealed that the party is actually Spears' wedding, as she starts walking towards the aisle and Federline waits next to a priest.

Considine of Rolling Stone noted 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'".

[131] Jamaican reggae singer Beenie Man covered "My Prerogative" for his 1998 studio album Many Moods of Moses.

[134] English rock band Selfish Cunt also covered the song for their 2004 studio album No Wicked Heart Shall Prosper, changing the name to "Bobby".

[135] In July 2007, American basketball player LeBron James covered "My Prerogative" at the ESPY Awards, wearing a wig and Hammer pants.

[137] Anoop Desai, contestant of the eight season of American Idol, covered the song for his wildcard round performance.

[139] On July 31, 2009, American hip hop group The Pharcyde covered the song at the All Points West Music & Arts Festival in Jersey City.

[141][better source needed] The song was performed in the 2013 Glee episode "Guilty Pleasures" by Jake Puckerman (Jacob Artist).

During the premiere episode of The Masked Singer, Pittsburgh Steelers wide receiver Antonio Brown covered "My Prerogative", incognito as a character known as "the Hippo".