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Bailey was inspired to go into acting after watching a making of Dawson's Creek special where they interviewed Katie Holmes.She attended the theater program at the Collin County Community College (Quad C) in Plano, Texas where she participated in productions of "suburbia", "Through a Glass Onion", and "Don’t Rock the Jukebox". Kent Williams, who spotted her at one of the plays, invited her to audition for Funimation, who had been working on Dragonball Z. Her most notable role on Dragonball Z was Kid Trunks. She voiced the starring character Marlene Angel in Blue Gender, which was the first project Funimation did outside of the Dragonball world, and Keiko Yukimura in Yu Yu Hakusho.
Bailey was cast for the starring role of Tohru Honda in the anime Fruits Basket. Bailey said that Tohru's character has helped her be more positive: "I was so inspired by her character by her, joy, and outlook on life that, you know, you wanna emulate that." She later voiced Lust, one of the villains in Fullmetal Alchemist, and Sana Kurata in Kodocha
Bailey had been working with Funimation for about four years before she started ADR directing. She worked on Blue Gender: The Warrior and some episodes of Case Closed. Her first major ADR Directing project was Gunslinger Girl, in which she also voices Henrietta. She also co-directed parts of Kodocha. She became a line producer for Shin-Chan and also voices the title character. She is voicing the Black Widow in Avengers Assemble.