In 1992 Wooley made his Broadway debut as an understudy (Big Moe) in the Clarke Peters' musical, Five Guys Named Moe. After Five Guys Named Moe he embarked on national tours with The Pointer Sisters in Ain't Misbehavin' and The Wiz with Stephanie Mills.
Wooley returned to Broadway in 2000 as Olin Britt in the Broadway revival of The Music Man, directed and choreographed by Susan Stroman.
Wooley's most recent Broadway role was as the voice of the man-eating plant, Audrey II, in the 2003 revival of the musical Little Shop of Horrors at the Virginia Theatre (renamed the August Wilson Theatre in 2005). Though his role was behind-the-scenes, theater critics took notice. Ben Brantley of the New York Times wrote Wooley had a "soulful bass voice" and Clive Barnes of the New York Post said that Wooley as the "doom-struck voice of Audrey II" rounded out "one of the best casts on Broadway"
Under the baton of Skitch Henderson, Wooley made his Carnegie Hall debut with the New York Pops as one of the "New Faces of 2004" along with other Broadway notables such as John Tartaglia and Stephanie D'Abruzzo. The event was hosted by famed New York Post gossip columnist Liz Smith.
Wooley played Tiny Joe Dixon in the 2006 motion picture, Dreamgirls, and sang the solo "Takin' The Long Way Home", the third song on the movie Soundtrack.
Jon-Marc McDonald, a close friend and sometimes-publicist for Wooley, confirmed on his website that Wooley performed We Have To Change at a fundraiser for Barack Obama in New York City on August 11, 2008. The song was specifically written for the fundraiser by Bill Russell and Henry Krieger.
In 2012 he voiced Impossibear from Pendleton Ward's Bravest Warriors which airs on Frederator's YouTube funded channel Cartoon Hangover.
He also was cast as the latest voice for Tobias Whale in the new Batman series, Beware the Batman. In 2014, he voiced Chill Bill from Sanjay and Craig as well as Master Lun in Kung Fu Panda: Legends of Awesomeness and Pumpers in Breadwinners. In 2015 and 2017, Wooley was a guest voice on Penn Zero: Part-Time Hero.
He voices Acorn and Achaka in the 2015–16 video game series King's Quest
