Culture
Britney Spears’ Most Iconic Cameo Performances
From The Simpsons to Pepsi commercials with original songs — in the 1990s and 2000s, Britney’s talent couldn’t be stopped.
Britney Spears is currently fighting in court to end the conservatorship by her father, who since 2008 has been in control of her life decisions and finances. She’s announced she’s recently retired, which, fair, because this pop star has given us more than we deserve since her groundbreaking debut Hit Me Baby One More Time was released in 1999. But Britney gave us more than music: Here, we take a look back at some of the pop star’s greatest cameos — roles where she played herself or guest-starred, in some of the most decade-defining shows and movies of the time.
Sabrina the Teenage Witch, Season 4, Episode 1 (1999)
Britney gets magically zapped into Sabrina’s living room for a private performance of “You Drive Me Crazy,” which is by far the best use of magic ever used on this show. Sabrina isn’t enjoying the concert because she’s alone, and Britney tells her she knows what it’s like to be lonely. (Oof.) But then they dance together! (Paramount+)
Pauly Shore Is Dead (2003)
In this brief cameo of the unhinged, fake documentary about the dwindling of Pauly Shore’s career, as the world celebrates Pauly Shore not actually being dead, Britney, as herself, keeps asking: “Who is Pauly Shore?” Then she realizes: “Oh, he was on MTV before me.” (Amazon Prime)
Will and Grace, Season 8, Episode 18 (2006)
Spears steals this scene from Jack (which is not easy to do!), playing a “lesbian into leather play” moonlighting as a conservative talk radio show host, with an exaggerated Southern accent, in what is her first acting performance on prime time TV. (Hulu)
Glee, Season 2, Episode 2 (2010)
This episode, dedicated entirely to Spears’ catalogue, is one of the greatest tributes to her work and is Glee at its best. The cheerleader Brittany has an anesthesia-fueled hallucination where the cast performs the best Britney Spears songs, and Britney makes a cameo as herself. Brittany tells Britney she’s really hot and her breath smells good, which is also what we would tell Britney Spears. (Netflix)