The singer released singles such as "Let's Tell Them Now" in 1960, in a smooth pop style retroactively described as pre-rock. He worked with longtime record producer and label manager Joe Davis a few years later, and wound up inspired by the idea of children as record buyers, or at least conduits to their parent's wallets. Talented young vocalist Leslie Uggams was one of the hotter irons Davis had in the fire during the period when he also contracted the somewhat lukewarm Clayton. Some of Clayton's efforts at winning the minds and hearts of the wee ones included a 1971 collaboration with songwriter Candy Anderson entitled "Lullaby and Goodnight." Vocalist Gladys Shelley gave it her all, but children were probably much more attracted to the back cover of this record, a full-color jigsaw puzzle of a tiger tail. "Stay out of That Empty Building," a title so nice it deserves to be repeated twice, also came out around this time and was cooked up with the help of Gail Contini (no relation to the tomato sauce manufacturer of the same name).
Clayton was happy to fill gaps in his schedule with background vocal and choral recording studio jobs, and continually made use of such opportunities during different parts of his career, including recording sessions with Frank Sinatra in one decade and Judy Collins in another. Clayton also tinkered with songwriting outside of the kiddie market. Peggy Lee recorded his demanding "All I Want" -- and there must be a lot of demanding songwriters out there, considering how many times this song title has been used. Clayton has sung on Broadway in shows such as The Wiz and in the early '90s was the featured vocalist with the Lew Anderson Big Band.