[1] During the five years they were together, the Jug Band successfully modernized the sounds of pre–World War II rural music.

The Jug Band released six albums and two greatest hits compilations on Vanguard Records between 1963 and 1970.

Kweskin is most often recognized as a singer and bandleader, but he is also known for his guitar stylings, adapting the ragtime-blues fingerpicking of artists like Blind Boy Fuller and Mississippi John Hurt, while incorporating more sophisticated jazz and blues stylings into the mix.

In the 1970s, Kweskin recorded some vocals for some Sesame Street inserts, most notably, "Ladybugs' Picnic".

[6] In the 21st century, he resumed making music, including tours and recordings with Geoff Muldaur, Meredith Axelrod, and Samoa Wilson.