In 1965, he collaborated alongside Skeeter Davis and their single, "A Dear John Letter", reached number 11 on the country chart.

The top 20 single, "Find Out What's Happening", was Bare's first to reach Canada's RPM Country chart, climbing to number five.

In 1969, "(Margie's At) The Lincoln Park Inn" reached the top ten of the American and Canadian country charts.

In 1970, Bare's first three singles for Mercury Records made the Billboard country top ten: "That's How I Got to Memphis", "Come Sundown" and "Please Don't Tell Me How the Story Ends".

Among his top 20 singles of this period included "Alimony" (1975), "The Winner" (1976), "Drop Kick Me Jesus" (1976), "Sleep Tight Good Night Man" (1978), "Numbers" (1979), "Willie Jones" (1980) and "New Cut Road" (1982).