On January 23, 2000, the twelfth episode of the season 11 of The Simpsons was originally aired. It was titled "The Mansion Family" and it featured the guest appearance of Britney Spears as herself. The episode was written by John Swartzwelder and directed by Michael Polcino.
"The Mansion Family" starts with the Springfield Pride Awards, which are being hosted by the cartoon version of Britney Spears and fictional character Kent Brockman. They present the award for Springfield's oldest citizen to Cornelius Chapman, who dies onstage from a heart attack after Britney Spears kisses him. The award then passes to Mr. Burns, who decides to get a checkup at the Mayo Clinic, leaving Homer in charge of his mansion.
In commemoration of the 25th anniversary of the show, NECA released a collection of figures based on some of the famous guest stars that have appeared throughout the series. A Britney Spears figure was released in the second batch of the collection.
You can watch the full episode here.