Well, maybe they’re not losers, strictly speaking. But the narrators in these songs have taken a look at themselves and found something lacking. Maybe it’s a self-esteem issue, or a crisis in confidence, or even a bout of self-loathing. In any event, they have our empathy—up to a point. Because as we all know, when you look back, a mea culpa or “my bad” sometimes resembles nothing so much as a shrewd chess move.

George Kalogerakis, one of the original editor-writers at Spy, later worked for Vanity Fair, New York, and The New York Times, where he was deputy op-ed editor. A co-author of Spy: The Funny Years and co-editor of Disunion: A History of the Civil War, he is a Writer at Large for AIR MAIL