[1] In 1968, O'Keefe was a member of a four-man heavy psychedelic rock band named the Calliope.

O'Keefe is best known for the hit single, "Good Time Charlie's Got the Blues", which was released in September 1972,[1] and reached number 9 on the U.S.

"Good Time Charlie" stayed on the Billboard chart for 14 weeks and sold a million copies.

[4] O'Keefe's songs have been covered by numerous musicians, including Jackson Browne ("The Road"),[1] Gary Stewart ("Quits"), Elvis Presley,[1] Glen Campbell ("Quits"), John Denver ("Along for the Ride"), Donny Hathaway ("Magdalena"), Leo Sayer ("Magdalena"),[1] Jerry Lee Lewis, Judy Collins ("Angel Spread Your Wings"),[1] Leon Russell, Willie Nelson, Waylon Jennings, Jimmy Buffett ("Souvenirs"), Alison Krauss, Ben Harper, Cab Calloway, Mark-Almond, Andy Williams, and Dwight Yoakam ("Under the Covers").

In Italy his song "The Road" has been covered by Ron, with Italian lyrics written by Lucio Dalla (and re-titled "Una città per cantare").