Cindy Cashdollar is one of the most accomplished and versatile string players in American roots music — a Woodstock, New York, native whose mastery of the Dobro, lap steel, and steel guitar has made her the go-to collaborator for artists ranging from Bob Dylan to Asleep at the Wheel. With five Grammy Awards and a career that spans nearly five decades, she represents the Woodstock musical tradition at its finest: deeply skilled, stylistically fearless, and rooted in community.
Woodstock Beginnings
Cashdollar grew up in Woodstock in the 1960s and 1970s, surrounded by the musicians who made the town synonymous with American music. As a young player in the late 1970s and 1980s, she developed her craft alongside Levon Helm and Rick Danko of The Band, bluegrass musician John Herald, blues legend Paul Butterfield, and folk artists Happy and Artie Traum. A formative Van Morrison concert at age 12 helped set her course. She mastered the Dobro — a wood-bodied guitar with a steel resonator cone — and expanded to lap steel, developing a sound that could move between country, blues, Western swing, bluegrass, and Cajun music with equal authority.
Asleep at the Wheel and Nashville
In 1992, Cashdollar joined Asleep at the Wheel, the legendary Western swing band, and spent nine years contributing steel guitar to their recordings and tours. During that period, she worked with Willie Nelson, Merle Haggard, Dolly Parton, and Lyle Lovett. Five Grammy Awards followed, earned primarily during her tenure with the band. She became the first woman inducted into the Texas Steel Guitar Hall of Fame in 2011 and the Texas Music Hall of Fame in 2012.
A Woodstock Life
Cashdollar’s collaborator list reads like a roots music encyclopedia: Bob Dylan, Ryan Adams, Van Morrison, Rod Stewart, Dave Alvin, Jorma Kaukonen, Leon Redbone, BeauSoleil, Daniel Lanois, and dozens more. After 23 years in Austin, she returned to Woodstock in 2015, closing a circle that began with those early sessions alongside Levon Helm. Her 2020 album Waltz for Abilene features guests including Sonny Landreth, Albert Lee, and Amy Helm. In a genre often dominated by men, Cashdollar has been the standard-bearer for slide and steel guitar for decades — and she’s done it from the same Woodstock community that shaped her from the beginning.