Following on the heels of the fluke success of Loudon Wainwright III's only hit single, "Dead Skunk," Attempted Mustache is an excellent encapsulation of all things Loudon. Even so, sales were disappointing, and Wainwright's audience did not expand beyond that of a small, loyal cult. The LP kicks off with "The Swimming Song," a tongue-in-cheek celebration full of clever lines, banjo pickin' and a touch of Doug Kershaw's Cajun fiddle. "A.M. World" reflects on life with a hit single, obviously written while "Dead Skunk" was climbing the charts. "Liza" is an a cappella folk song about childhood friend and classmate Liza Minnelli, who had recently won an Oscar for Cabaret.

"I Am the Way" recasts Woody Guthrie's talking blues "New York Town," with Jesus Christ hanging out in Jerusalem proclaiming, "Every Son of God gets a little hard luck some time," and confessing, "Don't tell nobody but I kissed Magdalene." "Dilated to Meet You" is a welcome-to-the-world greeting card for a soon-to-be-born child, but on "Lullaby," the singer pleads with his son Rufus to "shut up and go to bed," complaining "you're a late night faucet that's got a drip." This album also includes the Wainwright classic "The Man Who Couldn't Cry," a lengthy short story set to music about a character who suffers all manner of tragedy and abuse, but is still incapable of showing emotion. Throughout Attempted Mustache, Loudon Wainwright III's droll, dry sense of humor is conveyed by his world-weary Everyman's voice, capturing small vignettes of life through a skewed, slightly left-of-center lens.