Bailey attended Judge Memorial Catholic High School in Salt Lake City and graduated in 1996.
Growing up in Salt Lake City, Bailey was a performer in numerous theatrical productions and developed an interest in makeup artistry while assisting set artists.
By the age of 18, Bailey had moved to New York City, where he perfected his technique at makeup counters and through apprenticeships with artists including Kevyn Aucoin and Pat McGrath.
He worked with Katy Perry, Taylor Swift, Ashley Benson, Kate Beckinsale, Selena Gomez, Karlie Kloss and Gwen Stefani, among others.
[9] His death drew tributes from celebrities on his long list of clientele including Paris Hilton, Mariah Carey, Maria Menounos, Octavia Spencer, Katy Perry, Emmy Rossum, and Selena Gomez.