Cromwell started recording and touring with Joe Walsh in 1986,[2] appearing on two albums, Got Any Gum? and Ordinary Average Guy.

In 1987, Cromwell began a collaboration with songwriter Neil Young. The initial sessions became Neil Young & The Bluenotes. Since then he has recorded and toured with Young on several occasions, and appears on albums such as Freedom (1989), Prairie Wind (2005) Living with War (2006) and Chrome Dreams II (2007). He has also appeared in Heart of Gold, a documentary capturing the debut of Neil Young's album, Prairie Wind (along with other Young classics).[3] This was filmed at the Ryman auditorium and directed by Jonathan Demme.

Cromwell is also known for his contributions to Mark Knopfler's solo albums Golden Heart (1996), Sailing to Philadelphia (2000), The Ragpicker's Dream (2002) and Shangri-La (2004). He was also part of Knopfler's band during the tours of his first solo albums.[4]

Cromwell toured with Crosby, Stills, Nash & Young in the summer of 2006.[5]

He has also worked with many other artists including Dave Stewart, Vince Gill,[6] Amy Grant, Lady Antebellum, Diana Krall, Willie Nelson,[7] Jackson Browne,[8] Boz Scaggs, Wynonna,Trisha Yearwood, Miranda Lambert, Bonnie Raitt,[7] Peter Frampton,[9] Allison Moorer,[10] Chris Knight,[11] Joss Stone, Rodney Crowell, and Marty Stuart.

In the mid 2000s, Cromwell formed the band Fortunate Sons along with Michael Rhodes, Gary Nicholson, Kenny Greenberg, and Reese Wynans. They released a self-titled album in 2004.[12] He is also a member of the occasional touring band, Big Al Anderson and The Balls, led by former NRBQ guitarist Al Anderson.

In 2012, he appeared on The Beach Boys' studio album entitled That's Why God Made the Radio. In 2013, he was featured on Bonnie Tyler's album, Rocks and Honey.

Cromwell endorses Craviotto drums, Zildjian cymbals, DW Hardware, Vic Firth sticks, Universal Audio, Focusrite, and QuikLoc.