Paley is best known for, along with Mike Seeger and John Cohen, the formation of the New Lost City Ramblers in 1958. He decided to leave the group in 1962 because of political differences as well as a desire for less touring. After the break-up he helped form the Old Reliable String Band with Roy Berkeley and Artie Rose. After this group's break-up, He helped to for the New Deal Stringband. The band has been revived in recent years. Paley has also gained a reputation as a talented solo musician.