Tillotson was born April 20, 1939, in Jacksonville, FL, the son of Jack Tillotson, a country music disc jockey, and Doris Tillotson. When Tillotson was nine, he moved 40 miles to the smaller Florida town of Palatka. He got his first exposure as a singer on his father's radio station while he was still a child. His primary interest was country music, although he was inspired when he saw Elvis Presley perform in Jacksonville on May 13, 1955, just after he had turned 14. Meanwhile, his radio work led to a stint on a local TV show and even his own program. But he maintained his studies, and he was attending the University of Florida as a journalism and composition major in 1957 when he entered a national talent contest sponsored by Pet Milk. He was chosen as one of six finalists, resulting in a trip to Nashville, TN, for the final judging. He did not win the contest, but while in Nashville he came to the attention of a song publisher who was impressed by songs he had written and got a tape of them to Archie Bleyer, owner of the independent Cadence Records label, home to the Everly Brothers and Andy Williams. Bleyer signed Tillotson to a three-year contract and, in September 1958, issued his first single, combining two of the singer's own compositions, the ballad "Dreamy Eyes" and the up-tempo "Well I'm Your Man," both of which bore similarities to the sound of Buddy Holly. "Well I'm Your Man" charted first, peaking at number 87 in the Hot 100 in October, but "Dreamy Eyes" followed, topping out at number 63 in January 1959. (The simultaneously released "I'm Never Gonna Kiss You," a duet with Genevieve, a singer on the Jack Parr TV show, did not chart.) .......................... The relative failure of "Dreamy Eyes" sent Tillotson back to college, where he received his B.A. in 1959; that August 1959 Cadence released his next single, "True True Happiness," a song in the currently popular teen pop style, complete with recitations of romantic devotion; it petered out at number 54 in September. "Why Do I Love You So," which followed in December, suggested that Tillotson had been listening closely to Ricky Nelson's 1958 hit "Poor Little Fool"; it reached number 42 in February 1960. Next, Bleyer tried having Tillotson cover a couple of old R&B hits, combining the Penguins' "Earth Angel" and Johnny Ace's "Pledging My Love." Disc jockeys couldn't seem to decide which side of the single to play, and both peaked in the bottom half of the Hot 100 in May. .......................... Tillotson broke through to success with his sixth single, the bouncy pop/rock tune "Poetry in Motion," released in September 1960. He and Bleyer had finally found an appropriate forum for his clear tenor voice, recording with a Nashville studio full of country music session stars like saxophonist Boots Randolph and pianist Floyd Cramer. "Poetry in Motion" peaked at number two in November 1960; in the U.K., it hit number one in January 1961. Instead of immediately turning to extensive personal appearances, however, on Bleyer's advice Tillotson focused primarily on his recording career, though he appeared on television and began to be featured in teen magazines. "Jimmy's Girl," his next single, responded to this teen idol image, but it stopped at number 25 in February 1961. Singing another of his own compositions, Tillotson produced "Without You," a dramatic, string-filled production in the manner of Roy Orbison; it reached number seven in September 1961. Cadence then re-released Tillotson's first single, "Dreamy Eyes," and it got to number 35 in January 1962.