Kevin Grant Sharp was born December 10, 1970 in Redding, California. When he was seven years old, his family moved to Weiser, Idaho, to open a restaurant. Sharp performed in local musicals in high school, and stayed active in music after his family moved to Sacramento, California, in 1985. Starting in 1989, he began to experience dizziness and fatigue. He was diagnosed with Ewing's sarcoma, a rare form of bone cancer. Kevin Sharp was given little chance of recovery. Through the Make-A-Wish Foundation, which grants wishes to children with life-threatening illnesses, Sharp met the record producer David Foster, with whom he soon became friends. After two years of chemotherapy and radiation treatment, when still in his early 20s, the cancer went into remission by the early 1990s, although he permanently lost all of his hair as a result of the radiation treatment. In high school Kevin played football and basketball. He was unable to play football and basketball during his senior year because of his cancer. The doctors eventually discovered that the cancer had spread to his lungs. Kevin Sharp was a member of the Church of Jesus Christ of Latter-day Saints. Kevin Sharp graduated from Bella Vista High School.
After remission, Sharp worked at Great America in Santa Clara, California, while working on a demo tape, which he sent to various talent shows, and later to David Foster. Foster introduced him to A&R representatives and, by 1996, Sharp was signed to Asylum Records. His first album, Measure of a Man, was released in September 1996. The album's first single, a cover version of the R&B artist Tony Rich's "Nobody Knows", spent four weeks at number one on the Billboard Hot Country Singles & Tracks chart. He became a spokesperson for the Make-A-Wish Foundation, and was awarded the foundation's Wish Granter of the Year award, in 1997. He was named New Touring Artist of the Year by the Country Music Association and nominated for Top New Male Vocalist award by the Academy of Country Music.
In 1998, Sharp collapsed backstage at the TNN Music City News Country Awards, and was rushed to the hospital for emergency surgery, due to problems with steel rods in his hip. As a result, he had to cancel several tour dates. Measure of a Man produced two more top 10 country singles, "She's Sure Taking It Well" and "If You Love Somebody". The album's fourth single, "There's Only You", peaked at No. 43. His second album, Love Is, released in 1998 on Asylum, failed to produce any successful singles, and Sharp was dropped from Asylum's roster.

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