She made her voice acting debut as Kid Trunks in the Funimation dub of Dragon Ball Z and has since voiced Emily / Glitter Lucky in Glitter Force, Tohru Honda in Fruits Basket, Lust in Fullmetal Alchemist and Fullmetal Alchemist: Brotherhood, the title character in the Funimation dub of Shin-Chan, and Maka Albarn in Soul Eater.

Bailey's video game voice roles include Rayne in the BloodRayne franchise, Kira Carsen in Star Wars: The Old Republic, Kainé in Nier, Jaina Proudmoore in World of Warcraft, Rise Kujikawa in Persona 4, the Female Protagonist in Persona 3 Portable, Chun-Li in Street Fighter, Serah Farron in Final Fantasy XIII, the title role in Catherine, Serana in The Elder Scrolls V: Skyrim – Dawnguard, Persephone in the Skylanders series, Oriana Lawson in Mass Effect 3, Lucina in Fire Emblem Awakening, Kushina Uzumaki in Naruto Shippuden: Ultimate Ninja Storm series, Abigail "Fetch" Walker in Infamous Second Son and First Light, Fiona in Tales from the Borderlands, Nadine Ross in Uncharted 4: A Thief's End and The Lost Legacy, and Kait Diaz in Gears of War.

[1][4][5] She attended the theatre program at Collin County Community College in Plano, Texas,[4] where she participated in productions of the plays Suburbia, Through a Glass Onion, and Don't Rock the Jukebox.

[6] Voice actor Kent Williams spotted Bailey at one of her college plays and invited her to audition for Funimation while they were working on Dragon Ball Z.

[8] Bailey initially tried to do the role alongside her college career, but stopped attending on the advice of her lecturer to focus on voice acting.

Bailey's video game voice roles include Rayne in the BloodRayne franchise,[11] Jaina Proudmoore in World of Warcraft, Rise Kujikawa in Persona 4, the Female Protagonist in Persona 3 Portable, Chun-Li in Street Fighter, Serah Farron in Final Fantasy XIII, Blaze the Cat in Sonic the Hedgehog, the title role in Catherine, Serana in The Elder Scrolls V: Skyrim – Dawnguard, multiple characters in Fallout: New Vegas, Lucina in Fire Emblem Awakening, Abigail "Fetch" Walker in Infamous Second Son and First Light, Fiona in Tales from the Borderlands, Spartan Olympia Vale in Halo 5: Guardians, Nadine Ross in Uncharted 4: A Thief's End and The Lost Legacy, and Kait Diaz in Gears of War.

In 2001, she played a minor role in an episode of Walker, Texas Ranger (titled "Saturday Night") as the daughter of a club owner (Frank Stallone Jr.) with ties to the Mafia.

[25][17] In November 2019, Amazon Prime Video announced that they had acquired the streaming rights to this animated series, now titled The Legend of Vox Machina;[26] Bailey reprises her role as Vex.

[28][29] Bailey made an appearance in the season finale of HBO's live-action adaptation of The Last of Us in a cameo role as a Firefly nurse, a character she voiced in the original game.