Episode 18:

Cutie Patootie

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Britney’s first appearance on the Rosie O’Donnell Show was February 8, 1999 (Season 3, Episode 97), an episode which also featured Priscilla Presley and a mystery guest.

She next appeared on Rosie May 24, 1999 (Season 3, Episode 171), an episode that also featured Adam Sandler, where she performed Sometimes. And here’s the Kids’ Choice Awards performance that Rosie was talking about during the interview.

She appeared again on September 27, 1999 (Season 4, Episode 14), an episode where Brooke Shields also appeared, where Britney performed (You Drive Me) Crazy.

Britney’s next appearance was a full-episode special where Rosie joined her at her Miami performance on the (You Drive Me) Crazy Tour. The episode aired on May 12, 2000 (Season 4, Episode 164).

Britney came on the September 10, 2001 show (Season 6, Episode 5) to perform I’m a Slave 4 U and plug her third album. Sarah Ferguson also appeared on the episode.

Britney came back two months later on November 5, 2001 (Season 6, Episode 35) to further promote her album and Crossroads (coming out in a few months), as well as perform Not a Girl, Not Yet a Woman. Danny Glover and Emeril were also guests on this episode.

Britney’s last appearance on Rosie aired on February 14, 2002 (Season 6, Episode 104), an episode that also featured Dylan McDermott and musical guest Train.

If you want more Rosie O’Donnell Show nostalgia, check out the Rosie O’Donnell Show pop dive episode of Danny Pellegrino’s podcast, Everything Iconic.

Rosie is also featured in the book Ladies Who Punch, a behind the scenes look at The View by Ramin Setoodeh.

And here’s more about Rosie’s impact on Broadway ticket sales.

Thanks for listening!