That's So Raven was a classic Disney Channel show for four seasons, earning it a spin-off starring Kyle Massey and Rondell Sheridan and later a 2017 reboot produced by Raven Symone that threw it back to the original show in its fifth season.

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Being the early-2000's hit it was, the sitcom was home to plenty of guest stars over its four-season run on Disney Channel. Whether they were well-established actors, award-winning singing sensations, or someday-Disney stars, That's So Raven was the place to be for top talent.

Yvette Nicole Brown As Monica

Yvette Nicole Brown on That's So Raven

Years before she was the sweet but sassy Shirley Bennett on Community and her portrayal of movie theater manager Helen on Nickelodeon's Drake and Josh, actress Yvette Nicole Brown made a guest appearance on the rival channel's That's So Raven.

Brown played Monica, a dance studio receptionist who is in no mood for Raven and Chelsea's shenanigans involving sneaking into fictional popstar Pressure's latest music video.

Candace Cameron Bure As Courtney Dearborn

Candace Cameron Bure on That's So Raven

Now a Hallmark Channel leading lady, Candace Cameron Bure has never been a stranger to sitcoms. Between her long stints as DJ Tanner on Full House and Fuller House, Bure played opposite fellow child star Raven Symone on an episode of That's So Raven.

Bure played a history teacher named Courtney Dearborn whose unconventional teaching style convinces Raven and her friends to throw a "study party" that gets out of hand, putting their teacher's job on the line.

David Henrie As Larry

David Henrie on That's So Raven

Years before booking his own leading role on Disney Channel's Wizards of Waverly Place and its subsequent Disney Channel Original Movie, David Henrie had a recurring role opposite Kyle Massey on That's So Raven.

Henrie played Cory's best friend Larry for 12 episodes in the show's early seasons, best known for getting involved in Cory's money-making schemes and playing guitar in Cory's band Cory and the Boys.

Brenda Song As Amber

Brenda Song on That's So Raven

While Brenda Song is no stranger to Disney Channel, one of her first magical roles with the network was with a one-episode stint as Raven's popular classmate Amber on That's So Raven.

Only a few years later, Raven Symone would guest star as her That's So Raven character on Song's hit show Suite Life of Zack and Cody in the Disney Channel crossover event of the decade: That's So Suite Life of Hannah Montana.

Tiffany Haddish As Charlotte

Tiffany Haddish on That's So Raven

Tiffany Haddish's first-ever television appearance was in an episode of That's So Raven, where she played an unenthusiastic biodome tour guide named Charlotte.

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Haddish would go on to lend her comedic presence to Disney Channel's Phineas and Ferb the Movie: Candace Against the Universe and the 2023 remake of Haunted Mansion, opposite the likes of Danny DeVito and Rosario Dawson.

Jackée Harry As Dava

Jackee Harry on That's So Raven

Jackée Harry starred in the ABC sitcom Sister, Sister for six years, which would later air in syndication on Disney Channel. Harry went on to make several guest appearances on future Disney shows, the first being That's So Raven.

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Harry played Dava on the episode "Goin Hollywood," which was actually a test pilot for a new Disney Channel sitcom titled Better Days. Despite its all-star cast of Harry, Alyson Stoner, Allie Grant, and Skyler Samuels, the show got beat out by Hannah Montana, which had a similar premise.

Cody Linley As Daryl

Cody Linley on That's So Raven

Before he was mending Miley's achy breaky heart as Jake Ryan on Hannah Montana, Cody Linley had a small role in a Season 3 episode of That's So Raven as Daryl.

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Linley's character is the leader of Cory's new friend group, who convince Cory to apply their "five-finger discount" at a toy store, where they get caught shoplifting by Raven dressed as a security guard after a vision gives her a heads up on her brother's antics.

Haylie Duff As Catina

Haylie Duff on That's So Raven

Hilary Duff wasn't the only Duff to appear on Disney Channel, as her older sister Haylie Duff guest-starred on Season 2 of That's So Raven.

Duff plays Catina, a classmate who falls for Eddie when he starts getting his own psychic visions. But when Eddie's powers disappear and he's unable to tend to Catina's every want, she breaks up with the former psychic.

Cyndi Lauper As Ms. Petuto

Cyndi Lauper on That's So Raven

Singing sensation Cyndi Lauper guest-starred on Season 3 of That's So Raven where she got to see everyone else's true colors as a quirky art teacher named Ms. Petuto.

Lauper didn't have a huge role in the episode, but her eccentric character lives on as a memorable one. Interestingly, another Season 3 episode that tackled racism was titled "True Colors," after Lauper's hit song.

Paula Abdul as Undercover Superstar Host

Paula Abdul on That's So Raven

The then-American Idol judge had a guest appearance as the unnamed host of the fictional reality TV talent competition Undercover Superstar in this musical episode of That's So Raven.

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While the episode features song and dance numbers from Raven, Chelsea, and Cory, as well as The Baxter's singing the catchy Undercover Superstar theme song, Abdul's character of the undercover talent scout never actually gets to see them perform and the kids lose their chance at stardom.

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