Originally from Vernon, Alabama, Penn began his career as a performer, leading several white R&B bands around the Muscle Shoals area. Achieving early success by selling a hit song to Conway Twitty ("Is a Bluebird Blue?"), the songwriter eventually moved to Memphis, joining producer Chips Moman at his American Studios. Together the two, along with Penn's writing partner, organist Spooner Oldham, wrote and/or produced several hits for the Box Tops, such as "The Letter" and "Cry Like a Baby," throughout the late '60s.
Penn eventually returned to Muscle Shoals during the period when Atlantic Records vice president Jerry Wexler was bringing acts like Aretha Franklin and Solomon Burke down from New York to record there. This led to Franklin cutting the Penn/Oldham composition "Do Right Woman," and for the next several years, Penn compositions such as "Dark End of the Street," "Woman Left Lonely" and "I'm Your Puppet" became soul classics and were recorded by such greats as James Carr, Janis Joplin and Dionne Warwick, respectively.
Never really considered a performer, in 1994 Penn released the long awaited follow up to his 1973 solo album Nobody's Fool. This album contains Penn performances of songs that others are known for such as "I'm Your Puppet," as well as new material. Moments from This Theater followed in 1999. ~ Steve Kurutz