He has performed regularly with such icons as John Zorn, Anthony Braxton, Eliane Radigue, Ken Vandermark, Fred Frith, Evan Parker, and Yoshi Wada, as well as being a collaborator with some of the brightest lights of his generation like Chris Corsano, C. Spencer Yeh, Peter Evans, and Mary Halvorson. Wooley’s solo playing has often been cited as being a part of an international revolution in improvised trumpet.

Along with Peter Evans and Greg Kelley, Wooley is considered one of the leading lights of the American movement to redefine the physical boundaries of the horn, as well as demolishing the way trumpet is perceived in a historical context still overshadowed by Louis Armstrong. A combination of vocalization, extreme extended technique, noise and drone aesthetics, amplification and feedback, and compositional rigor has led one reviewer to call his solo recordings “exquisitely hostile”.