"Trouble Is a Man" is a ballad composed by Alec Wilder, the idiosyncratic American songwriter known for bridging art song and popular music. Wilder wrote both the music and lyrics for this piece, an uncommon practice for a composer who typically collaborated with dedicated lyricists such as William Engvick, Loonis McGlohon, Johnny Mercer, and Fran Landesman. The song personifies trouble as a masculine figure, adopting a conversational, almost cautionary tone that Wilder reinforces through a minor-key setting and deliberate balladic pacing. This thematic focus on character and moral warning reflects Wilder's broader artistic inclination toward psychological nuance over conventional romantic subjects. Though the exact date of composition remains undocumented, the tune attracted several distinguished vocalists. Sarah Vaughan recorded it for her 1967 album "It's A Man's World," produced by Quincy Jones. Ella Fitzgerald performed it with the Ernie Heckscher Big Band under the direction of Tommy Flanagan. Peggy Lee, Judy Holliday, and jazz singer Lorez Alexandria also recorded interpretations. Published by Edition Cavalier, the song never achieved the widespread standard status of Wilder's best-known compositions like "I'll Be Around" or "While We're Young," instead remaining a specialty item valued by vocalists drawn to its introspective character and narrative sophistication.