He was the voice of Louis the Alligator in Disney's Oscar-nominated animated feature film, The Princess and the Frog and played Judge Grady on the radio station WKTT in Rockstar's Grand Theft Auto IV.

Wooley performed in the national tour of Purlie,[1] after which, worked as a singing waiter on the Spirit of New York,[2] a dinner cruise ship that circles Manhattan.

[10] Wooley was the voice of Louis the jazz trumpet-playing alligator, in Disney's The Princess and the Frog; and Tiny Joe Dixon in the 2006 motion picture, Dreamgirls, singing "Takin' The Long Way Home" on the film's soundtrack.

Wooley's voice has been heard in many television ad campaigns for Reebok, General Motors, McDonald's, Dairy Queen, K-Mart, Oxygen Network and others.

[11] He made numerous guest appearances on Cosby,[12][13] Law & Order: Special Victims Unit,[14] The Knights of Prosperity,[15] Now & Again, Rescue Me[16] and The Rosie O'Donnell Show.

He was a guest singer on The Penguins of Madagascar in "The Falcon and the Snow Job" and voiced the DC Comics villains Darkseid and Kalibak on the animated series, Batman: The Brave and the Bold.