The song, written in a Western swing style,[4] is a nostalgic look by Buffett at the popular culture of his childhood. The title refers to the mustache style of the film character, Boston Blackie.
Cash Box called it a "laid back honky tonker with incredible lyrics and a totally believable performance from Jimmy."[5]Record World called it a "rinky-tink razmataz of a new soft shoe filled with nostalgia references."[6]
Buffett has stated, "the thing about writing a song like this is that the older you get, the more people there are who need an explanation of the characters in the song. I shudder to think how old Sky King's niece Penny is today. It all started with that two-toned Ricky Ricardo jacket. I can't wait for them to come back."[7]
"Pencil Thin Mustache" is a popular song with Buffett fans, and is often played at concerts, but is not part of "The Big 8" songs that he has played at almost all of his concerts. Recorded live versions of the song appear on You Had to Be There and Buffett Live: Tuesdays, Thursdays, Saturdays. Billboard described the song as "very well done and quite funny."[8]