Born in 1974 in Clatskanie, Oregon, Wooley first started on trumpet at a young age and was playing professionally with his father, a saxophonist, by his teens. After high school, he studied music at both the University of Oregon and University of Denver. Moving to New York in 2001, Wooley found a home in the Brooklyn improvisational music scene, working with a bevy of boundary-pushing artists, including John Zorn and Anthony Braxton, Ken Vandermark, Fred Frith, Evan Parker, and others. He debuted in 2005 with his solo trumpet album Wrong Shape to Be a Storyteller. Projects followed with Tim Barnes, Paul Lytton, and David Grubbs.
In 2009, he formed a trio with guitarist Mary Halvorson and bassist Reuben Radding for Crackleknob on Hatology. That same year, he released Throw Down Your Hammer and Sing, featuring Fred Lonberg-Holm on cello and electronics and Jason Roebke on bass. He also collaborated with equally adventurous trumpeter Peter Evans on a 2011 duo album and joined Belgian drummer Teun Verbruggen's avant-garde outfit Bureau of Atomic Tourism for a series of albums in 2014 and 2015. Also in 2015, he joined guitarist Joe Morris and saxophonist Evan Parker for Ninth Square.
Along with performing, Wooley is active on a variety of fronts. He is the founder of the For/With Festival, the editor of online journal Sound American, and the curator of the Database of Recorded American Music (DRAM). He also works as an educator, teaching at The New School for Social Research. Philosopher's Stone arrived in 2017 and found the trumpeter playing with saxophonist Ivo Perelman and pianist Matthew Shipp. In 2019, he released Columbia Icefield, a dreamy production with guitarist Halvorson, pedal steel guitarist Susan Alcorn, and drummer Ryan Sawyer. More works followed with Shipp, Perelman, and Mat Maneri, including 2019's Strings 3 and Strings 4. He also contributed to Whit Dickey's Morph in 2020. In 2021, he released Mutual Aid, showcasing eight ensemble concertos and featuring saxophonist Ingrid Laubrock, pianist Sylvie Courvoisier, vibraphonist Matt Moran, and others. ~ Matt Collar, Rovi