Songfacts®:

• Craig Finn has a knack for writing songs that begin like barroom anecdotes and end somewhere between a Greek tragedy and the last call bell. "Chips Ahoy!" starts with a premise of a woman who can predict the winner of every horse race simply by closing her eyes. It then quietly reminds us that supernatural gifts are no substitute for emotional availability. Winning at the track, it turns out, is rather less useful than winning at relationships.
• When the woman drops $900 on a sixth-race outsider named "Chips Ahoy!," the horse romps home by six lengths, and she and her boyfriend disappear into a week-long haze of celebration. Yet beneath the gambling windfall lurks a relationship already buckling under the weight of drugs, distance and disappointment. Finn's point is, if perfect clairvoyance and unlimited betting success can't solve your romantic problems, perhaps the issue lies somewhere deeper than the balance in your wallet.
• Craig Finn came up with the idea during a day at the races in Saratoga, New York, with his sister and her friends. "I thought, What if there was a woman who could see which horse would finish first?" he told Mojo magazine. "That's where 'Chips Ahoy!' came from."
  
  Finn said that around this period, he was collecting stories in bars while increasingly drawing on episodes from his own life to flesh out his songs.
• Finn explained on the Live at Fingerprints EP that the horse itself is almost incidental. The real story concerns a man pursuing a woman whose predictions are infallible. Common sense suggests that dating someone who can guarantee gambling riches should eliminate life's worries. Instead, as Finn deadpanned, "they still got some problems.
• Many Hold Steady devotees hear "Chips Ahoy!" as the opening chapter in a loose cycle of songs featuring the same mysterious clairvoyant woman. "The Weekenders" refers back to "that whole weird thing with the horses" and hints at her psychic abilities. "Yeah Sapphire" finds another battered soul leaning on a woman whose dreams keep proving true, while "Both Crosses" pushes the supernatural themes toward questions of faith, miracles and guilt. Finn has never insisted they're chapters in a strict narrative, but together they create one of the band's most intriguing recurring characters, a woman whose extraordinary gift repeatedly fails to make anyone's life appreciably easier.
• "Chips Ahoy!" is the second track on The Hold Steady's 2006 album Boys and Girls in America. Produced by John Agnello, whose résumé includes Sonic Youth and Dinosaur Jr., the recording captures the band's trademark blend of ragged bar-band swagger and heartland-rock grandeur, with echoes of Bruce Springsteen never far from the surface.
• Dana Kletter, formerly of Blackgirls and Dear Enemy and later a contributor to Hole's Live Through This, contributes backing vocals. Her harmonies appear throughout Boys and Girls in America, including on "You Can Make Him Like You" and "First Night."