Brenda Lee recorded "Break It to Me Gently" on August 31, 1961 with Owen Bradley producing the session at his Bradley Film and Recording Studio in Nashville: after another track from the same session, "Fool #1", had become a Top Ten hit. "Break It To Me Gently" was released as a single at the end of 1961 and reached number four on the US "Billboard" Hot 100 in January 1962. In 2008, the Brenda Lee version of the song was featured at the closing of season 2, episode 7 of the AMC series "Mad Men". Lee's "Break It to Me Gently" is on the track list of the CD "Pan Am: Music From and Inspired By the Original Series" set for release January 17, 2012.