Pennington first performed in a
western swing band called the Western Rhythm Boys, which performed in
Ohio. In 1958, he signed with
King Records and released "
Three Hearts in a Tangle" under the name Ray Starr. However, Pennington was dissatisfied with the recording, so he asked that it be withdrawn as a single. Pennington then took up record producer and
artists and repertoire jobs at the label, including a production credit on
Hawkshaw Hawkins' final album,
Lonesome 7-7203, one of the first country albums to feature both black and white
session musicians.
Roy Drusky covered "Three Hearts in a Tangle", taking his rendition to number 2 on the country charts in 1961. Pennington continued to perform in both the Western Rhythm Boys and another band called the Starliners. He also worked at a record store and released a
rhythm and blues single called "I Have to Laugh to Keep from Crying", also under the name Ray Starr.) before leaving. He moved to
Monument Records in 1969, where he charted five more times, but soon left that label to work at
RCA Records. While at RCA,
Waylon Jennings covered "I'm a Ramblin' Man" and took it to number 1, as Pennington continued to work as a producer for RCA artists such as
Billy Walker and
Norma Jean. In 1984, Pennington co-founded
Step One Records with Mel Holt.
Ray Price was the first act signed to the label, and fiddler
Clinton Gregory charted three Top 30 hits while on Step One.
Western Flyer,
Celinda Pink and
The Geezinslaws were also among the label's roster. While on Step One, Pennington recorded multiple albums with the Swing Shift Band, co-founded with steel guitarist
Buddy Emmons. This band charted with "Turn Me Loose and Let Me Swing" in 1988. Step One closed in 1998. ==Death==