During the 1991 and 1992 season, he was a drummer for the house band of Saturday Night Live.[1][2]
Along with Skerik, Brad Houser and Mike Dillon, he co-created the jazz-fusion band Critters Buggin.[3]
He has played with David Bowie, Fiona Apple, The Wallflowers, Macy Gray, Natalie Merchant, Tori Amos, Garbage and others.[3]
In 2016, 2019 and 2021[4] he won Modern Drummer magazine's readers poll in the Studio Musician category.[5] 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,[6] in 2019 and 2020.
Chamberlain joined Bob Dylan's Never Ending Tour in 2019 and played on his 2020 release Rough and Rowdy Ways.[7][8] He was succeeded by Charley Drayton when Dylan resumed touring at the end of 2021.[7][9]