In 1959, Worth had her first hit, called "Are You Willing, Willie," on Cherokee Records. The song peaked in the top 15 of the country music charts. In 1960, her song "That's My Kind of Love" went to the top 5, becoming her biggest hit. Jack Stapp signed the young singer to the "Grand Ole Opry"'s "Friday Night Frollic". As a result of her independent record label hits, she was signed to Columbia Records where she was produced by Don Law and Frank Jones. At Columbia, she recorded a single called "I Think I Know". The song was a Top 10 hit for Worth. In 1961, she released another single called "There'll Always Be Sadness". The single was not as successful as her other singles, but it did make the Top 25 that year. For almost two years, Worth was absent from the Country charts.