Greatest Hits: My Prerogative is a greatest videos DVD compilation by singer Britney Spears. Designed by Jim Swaffield, the highly interactive collection was released by Jive Records on November 9, 2004, it accompanied the greatest hits of the same name. The collection contained all of Spears's music videos from 1998 to 2004, including unreleased material from the shoot of "Outrageous". It also contained alternate versions of the videos with never before seen footage.
The DVD received positive reviews from critics, who complimented the quality of the audio and the image and also deemed Spears as the ultimate video performer. Greatest Hits: My Prerogative debuted at the top of the DVD charts in Australia, number two in Hungary and number nine on Billboard's Top Music Videos. It was also certified two-times platinum in countries such as Argentina, Australia and the United States.
On August 13, 2004, Spears announced through Jive Records the release of her first greatest hits compilation titled Greatest Hits: My Prerogative, due November 16, 2004. A DVD would also be released the same day, containing Spears's music videos. The compilation took four months to be assembled, as crews from her record label combed through unedited and unused footage, instrumentals and alternate audio. The DVD provided two menus — one which contained all of Spears's music videos to date, as well as scenes from the unreleased video of "Outrageous"; and other for alternate versions with never before seen footage from "...Baby One More Time", "(You Drive Me) Crazy", "Oops!...I Did It Again", "Stronger", "Don't Let Me Be the Last to Know", "I'm a Slave 4 U", "Toxic", "Everytime" and "My Prerogative". Among the highlights of the alternate takes were new vocal mixes in "(You Drive Me) Crazy" and "I'm a Slave 4 U" and a karaoke version of the diamonds scene of "Toxic". The video also included hidden footage, such as a third alternate version of "My Prerogative". The release date for the DVD was later moved to November 9, 2004.
James Griffiths of The Guardian commented, "Here comes the Queen of Pop in a box so shiny you can see your face in it. Spears is described on the cover as 'the ultimate video performer', and watching the 20 promos contained within, it's difficult to argue. [...] Relentlessly thrusting herself at the camera, compulsively preening amid special FX galas, Britney is the MTV video age in human form." He also complimented the innovations of the menu, but added that "it's not particularly impressive" and "you need to be pretty nifty with your handset to find them."Music Week said, "The DVD version of Spears' high-flying 'best of' set adds bells and whistles to the audio version at only a slight premium pricewise. Twenty promo videos are included, all with top-notch sound and vision".Allmusic gave the compilation four and a half stars out of five.Rolling Stone graded it with three out of five stars.