《My Prerogative》was covered by pop artist Britney Spears for her Greatest Hits: My Prerogative album. The music video was directed by Jake Nava and depicts a wedding reception party for Spears and her real-life husband at the time Kevin Federline. Her music video was chosen by Rolling Stone magazine as the best music video of 2004, whereas MuchMusic's Fromage chose it as the worst music video of 2004.