During the 1991 and 1992 season, he was a drummer for the house band of Saturday Night Live.
Along with Skerik, Brad Houser and Mike Dillon, he co-created the jazz-fusion band Critters Buggin.
He has played with David Bowie, Fiona Apple, The Wallflowers, Macy Gray, Natalie Merchant, Tori Amos, Garbage and others.
In 2016, 2019 and 2021 he won Modern Drummer magazine's readers poll in the Studio Musician category. In 2014 he filled in for drummer Matt Cameron in Soundgarden. He played over 51 shows with them through South America, Europe and a co-headlining tour with Nine Inch Nails in the United States. In October 2019, he joined Bob Dylan for his Fall Tour.
He was the Music Director for More Music @ The Moore Theatre Seattle, Washington, in 2019 and 2020.
Chamberlain joined Bob Dylan's Never Ending Tour in 2019 and played on his 2020 release Rough and Rowdy Ways. He was succeeded by Charley Drayton when Dylan resumed touring at the end of 2021.