Kurt Rosenwinkel attended the Berklee College of Music for two and a half years before leaving in his junior year to tour with Gary Burton, the dean of the school at the time. Subsequently, Rosenwinkel moved to Brooklyn, where he began performing with Human Feel, Paul Motian's Electric Bebop Band, Joe Henderson Group, and the Brian Blade Fellowship.
In 1995 he won the Composer's Award from the National Endowment for the Arts and was signed by Verve Records. Since then, he has played and recorded as both a leader and sideman with Mark Turner, Brad Mehldau, Joel Frahm, and Brian Blade, as well as many others. During Rosenwinkel's tenure with Verve he collaborated with Q-Tip of A Tribe Called Quest, who co-produced his studio album Heartcore that features bassist Ben Street, drummer Jeff Ballard, and saxophonist Mark Turner. He would further collaborate with Q-Tip, performing guitar on the latter's albums The Renaissance and Kamaal/The Abstract.
Currently he tours with his own projects (Caipi Band, Bandit 65, Standards Trio) so as a sideman (Oman Hakim & Rachel Z).
Originally from Philadelphia, Rosenwinkel attended the Philadelphia High School for the Creative and Performing Arts. Nowadays he lives in Berlin, Germany, where he runs his own independent record label Heartcore Records.