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In 2015, he joined the faculty of McGill University’s Schulich School of Music.

His second large ensemble recording, Joys and Desires, featuring Jazz Big Band Graz and Theo Bleckmann, was released by Intuition in 2006 to critical acclaim. The Claudia Quintet received four-star reviews from DownBeat and The Guardian for its fourth recording, For (Cuneiform, 2007), and was named "Rising Star Acoustic Jazz Group" in DownBeat's 2008 Critics Poll.

Hollenbeck was a professor of Jazz Drums and Improvisation at the Jazz Institute Berlin from 2005-2016.

Hollenbeck's chamber piece, Demütig Bitten, was commissioned by the Windsbacher Knabenchor (Germany) and released in 2004 on the Rondeau label with works by Giovanni Gabrieli, Josquin des Prez, and J. S. Bach. His commission through Bang on a Can and the People's Commissioning Fund was performed by the Bang on a Can All-Stars at Merkin Hall in New York City, February 2006. His commissions through the Ethos Percussion Group funded by the Jerome Foundation, and Youngstown State University, were premiered at the Whitney Museum, New York City, in October 2007.

In 2002, his IAJE Gil Evans Fellowship Commission piece, A Blessing, featuring vocalist Theo Bleckmann, was performed to critical acclaim at the IAJE Conference; and in 2003 his IAJE/ASCAP Commission, Folkmoot, was premiered in Toronto, Canada. In addition, he composed and performed the percussion score to the following Meredith Monk works: Magic Frequencies; Mercy (ECM, 2002); and The Impermanence Project (ECM, 2008).

Hollenbeck's recording career as a leader began in the winter of 2001 with: no images, which Gary Giddins included in his Village Voice 2001 top ten list, Quartet Lucy, and the Claudia Quintet. His second Claudia Quintet recording, I, Claudia, appeared on Cuneiform in 2004, followed by Semi-Formal in 2005.

In 1998, he composed The Shape of Spirit, a piece for wind ensemble on Mons Records, and in 1999 composed Processional and Desiderata for wind ensemble and orator. This composition, written for and featuring the voice and trombone of Bob Brookmeyer, was released on Challenge Records in 2001. The Cloud of Unknowing, commissioned by the Bamberg Choir in Germany was released in 2001 on the Edel Classics label with works by J. S. Bach, Igor Stravinsky, and Paul Hindemith.

After receiving degrees in percussion and jazz composition from the Eastman School of Music, Hollenbeck moved to New York City in the early 1990s. He has worked with Bob Brookmeyer, Fred Hersch, Tony Malaby, the Village Vanguard Orchestra, Kenny Wheeler, Pablo Ziegler, and Meredith Monk.