Kershaw tried to enter politics, running as a Republican candidate for lieutenant governor of Louisiana in 2007 and 2010. In 2007 he finished third in the jungle primary, but Democrat Mitch Landrieu won strongly in the general election. In 2010 he carried more parishes than any other candidate, but placed third. He endorsed Republican Jay Dardenne, Secretary of State, for the position, who won the general election.
Sammy Kershaw was born in the Acadiana town of Kaplan, located in South Louisiana. He is the third cousin of singers Rusty and Doug Kershaw. When he was 11, his grandfather gave him his first guitar. But his father died that year, so Sammy started to work a variety of day jobs while playing roadhouses at night to support his family. He began performing in Acadiana with Louisiana legend J.B. Pere. At the age of 12, Kershaw was playing in a variety of honky-tonks and beer joints, and when he was 14 he met George Jones, his lifelong idol. Subsequently, he opened shows for Ray Price, Merle Haggard, and George Jones while still barely into his teens. When the pressures of growing up fast took their toll in the form of a serious drug and alcohol problem, he quit his bad habits in 1988. He took a break from the music world to work as a remodeling supervisor at Wal-Mart.
One of Kershaw's demonstration tapes made its way to Mercury Records, which released his debut album Don't Go Near the Water in 1991. This album was certified platinum by the RIAA, and it produced four hit singles. The lead-off, "Cadillac Style", went to No. 3 in late 1991 and early 1992, followed by the title track at No. 12, "Yard Sale" at No. 17, and "Anywhere but Here" at No. 10. Kershaw was initially reluctant to release "Cadillac Style" because he felt that it was not suitable for his style; however, his co-producer, Buddy Cannon, convinced him to give the song a chance. Kershaw's often honky-tonk material and singing voice led to critical comparisons to George Jones, and he covered one of Jones's early singles, "What Am I Worth", on his debut as well.

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