Bailey was born in Birmingham, Alabama and relocated with her family to the Pensacola, Florida area at age two.

[4] In 1999, Bailey at age 17 made her on-screen debut on The Sopranos episode "Boca" as character Deena Hauser.

[1][5][6] Bailey hosted an April Fools Day episode of Slime Time Live on Nickelodeon in 2003.

In 2004, Bailey co-hosted a children-oriented Super Bowl XXXVIII pre-game show on Nickelodeon.

[9] After Jericho was cancelled, Bailey worked as a cocktail waitress and babysitter between acting jobs.