Originally recorded for Paul Simon's 1965 UK-only debut, The Paul Simon Songbook, the song title name-checked then-current US Secretary of Defense Robert McNamara. According to Simon, he was mostly channeling Lenny Bruce. He recalled years later:

"I was having fun. I thought it would be funny to use those unusual words 'desultory' and 'philippic,' in a song title, and I also wanted to sneak in some Lenny Bruce, who was my favorite comedian. That line, 'How I Was Robert McNamara'd Into Submission,' is pure Lenny."

Paul Simon re-recorded the song in 1966 with his partner, Art Garfunkel, for the duo's third album Parsley, Sage, Rosemary and Thyme. That version features several changes to the lyrics.