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Sabrina, the Teenage Witch, 1999
Thanks to some magic (duh) Britney performs a private concert for Sabrina and gives the teen some life advice. It's a bit depressing to hear a young Spears talk about how lonely she is, even if it's in the context of a TV show.
Spears and Melissa Joan Hart were basically a dream team in 1999. Remember, Hart appeared in Spears' video for "(You Drive Me) Crazy," which was featured on the soundtrack of Hart's movie Drive Me Crazy.
Kenan & Kel, 1999
Kenan and Kel meet Britney on an excursion to Hollywood. Kel does Britney's hair; it doesn't go well. (Though Spears' hair would eventually go through worse.)
Saturday Night Live, 2000
Britney deliciously spoofed tabloid speculation about her boobs during her SNL monologue when she hosted in 2000.
The Simpsons, 2000
One of Spears' many gigs through the years? Springfield awards show host. Her kiss can be deadly.
Will & Grace, 2006
The latter seasons of Will & Grace overdid it on the celebrity guest stars. But Spears gave this one her all, playing a conservative pundit who was secretly a lesbian. The show was long indebted to Spears, though. Note this earlier homage to her "Oops!" moves.