Greatest Hits: My Prerogative received little promotion as Spears injured her knee in June 2004 and was left unable to perform, but produced two singles.

[14] During the tour, Spears had recorded two new songs, which would appear on Greatest Hits: My Prerogative, and began a relationship with American dancer Kevin Federline.

[n] Within that period, Spears embarked on a prolonged hiatus from performing, both due to the injury and to start a family;[17] she wouldn't release another studio album until Blackout (2007).

Retrospectively, Stephen Thomas Erlewine from AllMusic noted that Spears "hadn't been out of the pop culture headlines since she released her debut album, ...Baby One More Time, in January 1999.

In the nearly six years separating that debut album and the release of Greatest Hits in November 2004, Britney was omnipresent, representing both the entire teen pop phenomenon of the turn of the millennium, plus the teasing, Maxim-fueled sexuality of the time".

[1][19] "My Prerogative" is a cover of Bobby Brown's 1988 song of the same title, with the original version's lyrics altered to fit a woman's perspective: "They say I'm nasty, but I don't give a damn / Getting boys is how I live / Some ask me questions, why am I so real?

[1] The cover is musically different from the bass-infused new jack swing original, showcasing a more contemporary synthpop sound, driven by synthesizers and elements typical of Bloodshy & Avant productions.

[20][21] Jennifer Vineyard of MTV commented the cover could be interpreted as a statement on Spears' life and the media reactions to some of her decisions at the time, including her engagement to Kevin Federline.

[23] In the United States, it was made available as a free digital download on the Walmart-exclusive edition of In the Zone, due to an exclusive deal with Walmart and Sony Connect.

[1] "Do Somethin'" is an electric guitar-driven dance-rock track, "filled with faux string bursts and mock-'70s synth gurgle (think Zapp/Gap Band era) and plenty of treated guitar and bass".

[24] Due to a knee injury, which had occurred during the music video shoot for "Outrageous" on June 8, 2004, Spears cancelled the remainder of the Onyx Hotel Tour and embarked on a prolonged hiatus from performing.

[36] It received critical acclaim,[18][37] and reached the top ten in Australia, Belgium, Croatia, Denmark, Greece, Hungary, Ireland, the Netherlands, Romania, Sweden and the United Kingdom.

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.

[43] 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".

[47] Christy Lemire of the Associated Press stated that it was premature for Spears to release a greatest hits album after only five years, but highlighted "I'm a Slave 4 U", "Toxic" and "Everytime".

[48] 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".

"[24] James Gashinski of The Gazette said: "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".

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.

"[37] Kelefa Sanneh of The New York Times said: "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".