Rainwater was one of country's most noteworthy stars in the late 1950s, when his good looks and baritone voice made him popular. One of the first country songs he recorded was "Gonna Find Me a Bluebird", which he wrote. Released in 1957, the song became a big country-pop crossover hit, making Rainwater among the first country singers to appeal to a pop market. The song reached No. 3 on the country chart and 18 on the pop chart. It sold one million copies by 1957, and gave Rainwater his first gold record. During the song's success, Rainwater relocated to the New Jersey-New York area. "The Majesty of Love" (1957) was a duet with Connie Francis, which also sold over one million copies. His next single, "So You Think You Got Troubles", was a successful follow-up on the country charts, but not on the pop charts. His self-penned "Whole Lotta Woman" reached UK No. 1 for three weeks in April and May 1958. A second UK single, "I Dig You Baby", made No. 19 in June 1958. "Nothin' Needs Nothin' (Like I Need You)" missed the UK Top Thirty chart, but returned him to the US Country chart.