Greatest Hits: My Prerogative received mixed reviews from music critics. Some felt that it was an accurate portrayal of Spears as the defining figure of American pop culture, while others stated that she did not have enough material for a greatest hits album and also deemed it as premature. Greatest Hits: My Prerogative peaked atop the charts in France, Greece, Ireland and Japan, and within the top ten in Australia, Austria, Belgium, Canada, Czech Republic, Denmark, Finland, Hungary, Italy, the Netherlands, Norway, Portugal, Switzerland, the United Kingdom and the United States. It was certified platinum by the Recording Industry Association of America (RIAA) and has sold over five million copies worldwide, selling over one and a half million copies in the United States.
The title track was released as the lead single from the album. It went on to peak atop the charts in Ireland, Italy, Finland and Norway, and reached the top ten in Australia, Austria, Belgium, Brazil, Czech Republic, Denmark, Germany, Greece, Hungary, Portugal, Spain, Sweden, Switzerland and the United Kingdom; however, it failed to enter the US Billboard Hot 100", topping the US Bubbling Under Hot 100 Singles. "Do Somethin'" was released as the second and final single from the album, and peaked at number hundred on the US Billboard Hot 100 although it wasn't released in the United States, but, however, reached the top ten in Australia, Greece, Hungary, Ireland, Sweden and the United Kingdom.
On August 13, 2004, Spears announced through Jive Records the release of her first greatest hits compilation titled Greatest Hits: My Prerogative, due on November 16, 2004; it was, however, released a week earlier in the United States. The title was chosen after the album's lead single, Spears's cover version of Bobby Brown's song "My Prerogative" (1988). The cover was produced by Swedish production team Bloodshy & Avant. A video compilationof the same title was also released the same day, containing Spears' music videos. Spears had recorded a song titled "(I've Just Begun) Having My Fun" originally for her fourth studio album In the Zone (2003). It was first included as a bonus track on the European edition of the video album In the Zone. In the United States, the track was a free download on the Walmart edition of In the Zone, due to an exclusive deal with Walmart and Sony Connect. When the deal ended in mid-2004, Jive Records decided to release it on iTunes Store on August 17, 2004. "I've Just Begun (Having My Fun)" peaked at number seven on the iTunes chart while it was speculated to be in the track listing of Greatest Hits: My Prerogative. The track listing was officially revealed on September 13, 2004. Greatest Hits: My Prerogative included three new tracks: "My Prerogative", "I've Just Begun (Having My Fun)" and "Do Somethin'", all of them produced by Bloodshy & Avant. A limited edition of the album was also released, which included a bonus disc with remixes of Spears' songs by different recording artists, as well as a megamix of Spears' hits.
Greatest Hits: My Prerogative received mixed to positive reviews from music critics. Mary Awosika of the Sarasota Herald-Tribune selected "(I've Just Begun) Having My Fun" as the best of the new tracks, and added that "The rest of the album is a romp down memory lane of when Spears was the 'It' girl of popular culture, ruling the pop charts as a multi-million dollar entertainment should. [...] In all honesty, no one can deny Spears has recorded some great dance songs, and this album is the best way to get all the songs in one swoop". Faridul Anwar Farinordin of the New Straits Times said, "rest assured, fans will surely grab this one" and selected "Oops!... I Did It Again" and "Overprotected" as the best tracks. Annabel Leathes of BBC Online deemed it "calorific as the KFC burgers dished up at her chav-style wedding; twenty finger lickin' tracks that mirror her trajectory from pretty pop puff to lusty strumpet". Christy Lemire of the Associated Press stated that it was premature for Spears to release a greatest hits album compilation after only five years, but highlighted "I'm a Slave 4 U", "Toxic" and "Everytime". Andy Petch-Jex of MusicOMH highlighted the first four tracks and commented "true some of the tunes are complete pony plops, but beneath the occasional reek there beats a solid gold pop heart".
Spence D. of IGN said, "If Britney Spears' Greatest Hits: My Prerogative illuminates anything it's that Spears is a fairly proficient sonic chameleon, able to mimic and adopt the stylings of those who have come before her with enough panache and verve to convince younger generations that she's a bona fide pop revelation. [...] This is the kind of kitschy album that you can get away with having because Spears is such a prevalent component of pop culture." James Gashinski of The Gazette said that "As a time capsule, My Prerogative does its job well," but "Added together, the pop hits on this album are somewhat less than the sum of their parts". He explained, "Even if it isn't as great a listen as a cohesive album, My Prerogative does work as a portrait of the time when Britney Spears was the defining figure of American pop culture". Stephen Thomas Erlewine of AllMusic agreed with Gashinski, but added "if you compare it to The Immaculate Collection, which captured the time when Madonna was the defining figure of American pop culture and does work as an album, it's clear that a cultural artifact isn't necessarily the same thing as great music".
Ann Powers of Blender said, "The hits collected on My Prerogative are as sticky as soda and almost as easy to rinse out. Spears will go down in history books, but not for anything she’s created, besides a world-class stir". She named "...Baby One More Time" "the song that defined her legacy" and also added: "In less than five minutes, it contains an emotional storm that is both widely public and deeply personal. If only she had continued to prove worthy of that heroic task." Kelefa Sanneh of The New York Times said that "Listening to her hits all at once, you may be struck by the seductive severity of Ms. Spears's music: the beats are sharp as tines, the lyrics are filled with evocations of fear and control, the voice projects nothing you might mistake for warmth".
In the United States, Greatest Hits: My Prerogative debuted at number four on the Billboard 200, with sales exceeding 255,000 copies. It has spent a total of thirty-two weeks overall on the chart. The album also became her first album not to debut at number one. In December 2004, the album was certified platinum by the Recording Industry Association of America (RIAA) for shipments of a million copies. As of March 2015, Greatest Hits: My Prerogative has sold over one and a half million copies in the United States. The album debuted at number three on the Canadian Albums Chart, selling 20,400 copies and was certified gold by the Canadian Recording Industry Association (CRIA) for shipments of 50,000 units. In Australia and New Zealand, Greatest Hits: My Prerogative debuted at number four and seventeen on the official charts, respectively. The album was certified double platinum by the Australian Recording Industry Association (ARIA), indicating shipments of 140,000 units.
In the United Kingdom, Greatest Hits: My Prerogative debuted at number two on the UK Albums Chart, behind Eminem's Encore, with first-week sales of 115,341 units. The album debuted at number three on the European Top 100 Albums.Greatest Hits: My Prerogative also debuted at number two in Belgium (Wallonia), Finland and Denmark, number four in Austria and Norway, and inside the top ten in Belgium (Flanders), Czech Republic, Italy, Portugal, Spain and The Netherlands, also charting top fifteen in Sweden. In Japan, the album became her first album to top the Oricon Albums Chart, selling 173,145 copies, and finished as the thirty-eighth best-selling album of 2004 and the fortieth of 2005. To date, it has sold 710,124 copies in the country and remains her highest-selling album there. Worldwide, sales of Greatest Hits: My Prerogative stand at over five million copies.
"My Prerogative" was released as the first single from the compilation. The song was set to premiere on radio stations on September 14, 2004, however, it leaked in the Real Tapemasters Inc.'s mixtapeThe Future of R&B on September 10, 2004. The cover was musically different from Bobby Brown's original song, and was noted for aptly referring to Spears's relationship with the media at the time. It received mixed to negative reviews from critics, but went on to achieve worldwide success, topping the charts in Finland, Ireland, Italy and Norway, and reaching the top ten in another fourteen countries.
In the United States, "My Prerogative" charted on Mainstream Top 40 at number twenty-two and topped the Bubbling Under Hot 100 Singles, failing to enter Billboard Hot 100
Although no more singles were planned, Spears wanted to shoot a music video for "Do Somethin'" and pushed for it to be released. The song was released as a single outside North America on February 14, 2005 (Valentine's Day). "Do Somethin'" received positive reviews, and reached top ten positions in Australia, Denmark, Greece, Hungary, Ireland, Sweden and the United Kingdom. Although the song wasn't released in the United States, it charted on Billboard's component charts due to digital downloads and reached number 100 on the Billboard Hot 100. The accompanying music video was co-directed by Billie Woodruff and Spears, who was credited as her alter ego "Mona Lisa". She was also the stylist and choreographer of the video.