As a session musician, he has worked with Billy Joel, Barbra Streisand, Rodney Crowell, and Vince Gill.

[1] He also co-wrote with Diamond, including the up-tempo "Forever in Blue Jeans" from the 1978 album You Don't Bring Me Flowers, which reached the Top 20.

Formed in the late 1970s as Rodney Crowell's road band, The Notorious Cherry Bombs' original members include guitarists Vince Gill and Richard Bennett, keyboardist Tony Brown, steel guitarist Hank DeVito, drummer Larrie Londin and bassist Emory Gordy, Jr. With a modified lineup the musicians went to the studio in early 2004 to record The Notorious Cherry Bombs, their first album as a band.

His quiet, self-effacing manner hides an encyclopedic knowledge of all kinds of roots and rock music, from Hillbilly to Hawaiian, played effortlessly on a variety of instruments which appear out of a flight case as big as an Airstream trailer... May his cracking guitar playing find a place in your life as it has in mine."

Bennett's electric guitar intro to Emmylou Harris' "Heaven Only Knows" (from her Bennett-produced Bluebird album) was the first sound heard on the 2004 season-opening episode of The Sopranos.