In 1959, he finally made his breakthrough with hits like "It's Just a Matter of Time" and "Endlessly". "It's Just a Matter of Time" peaked at #3 on the United States "Billboard" Hot 100 chart, sold over one million copies and was awarded a gold disc by the RIAA. "Endlessly" made it to #12. Both of the first two hits were written by Benton with Clyde Otis. They were originally offered to Nat King Cole, but when Otis became an A&R manager and producer at Mercury, he convinced Benton to sign with the label and record them himself, while asking Cole not to record the songs as planned. Benton followed this success with a series of hits, including "So Many Ways" (#6), "Hotel Happiness" (#3), "Think Twice" (#11), "Kiddio" (#7), and "The Boll Weevil Song" (#2). In 1960, he had two top 10 hit duets with Dinah Washington: "Baby (You've Got What It Takes)" (#5) and "A Rockin' Good Way (To Mess Around and Fall in Love)" (#7).