At the races and on stage with The Hold Steady's Craig Finn

When Craig Finn talks about his song “Chips Ahoy!”, the lead singer of The Hold Steady sounds like The Most Interesting Man in the World, but he’s talking gambling instead of alcohol.

“I'm not much a gambler,” Finn said. “But if you're going to gamble, the only thing worth gambling on is horse racing.”

Finn conceived the song while attending the races at Saratoga Race Course. His sister’s husband is from the area, and summer visits to the family usually include a trip to the racetrack.

On one such visit earlier this decade Finn took a call from his publicist but told her he couldn’t talk long because he was at the track.

“She said, ‘Put $50 on Chips Ahoy for me,’ and I said, ‘That’s going to be song.’ Four weeks later it was,” Finn said September 21. The track appears on Boys and Girls in America, the band’s third album and released in fall 2006.

In the song, Finn sings the role of a boyfriend whose girlfriend can predict the winner of horse races. They use the money to lead a careless existence involving drugs and no responsibility, but the boyfriend is unhappy because the relationship lacks intimacy.

The song begins, “She put $900 on the fifth horse in the sixth race; I think it’s name was Chips Ahoy. [It] came in six lengths ahead; we spent the whole next week getting high…”

Eventually, the narrative moves from success at the track to failure in the bedroom. “How am I supposed to know if you’re high if you won’t let me touch you? How am I supposed to know that you’re high if you won’t even dance?”

Finn has said during live performances of the song that he has asked those exact questions to girls from his past but whether such a performance will occur during the band’s first ever tour stop in Lexington on September 29 at Buster’s Backroom and Billiards will be a “game time” decision.

"It's one of our biggest songs, so it ends up in our shows more than others," Finn said.

The current tour began September 20 in Richmond, Virginia, and includes two Kentucky dates: the aforementioned Lexington show and a gig October 2 at Southgate House in Newport across the Ohio River from Cincinnati.

The fall tour comes on the heels of a Summer tour the band used to back its fifth studio album, Heaven Is Whenever released in May. Finn is known for his narrative lyrics, and Heaven is Whenever continues the “Chips Ahoy” narrative with the song “Weekenders” in which the narrator from “Chips Ahoy” tries to get back together with his clairvoyant former flame.

“I’m not on Facebook, but my girlfriend is, and I’ve been fascinated with the way people are making all these reconnections,” said Finn. “’Weekenders’ answers the question, What if a few years down the road the guy from ‘Chips Ahoy’ gets on Facebook and finds her and says, ‘We should get together.’”

“Weekenders” hints that the narrative of “Chips Ahoy” took place at an off-track betting parlor rather than at the track. Indeed, the “Chips Ahoy” video appears to take place at a hotel you’d find off U.S. Route 50 in Nevada rather than anything racetrack related.

“When ‘Chips Ahoy’ came out, Spin Magazine did a photo shoot with us at Monmouth Park, so after that we kind of asked ourselves how far did we want to go with the racetrack scene,” Finn said. “That hotel is way East of [Los Angeles].”

Before September 23, “Chips Ahoy!” would have been Finn’s most well-known sports song, but the singer penned the lyrics and sings lead vocals on the Baseball Collective’s “Don’t Call Them Twinkies,” a song that pays tribute to the Minnesota Twins. Finn was born in Boston but crew up near the Twin Cities in Edina, Minnesota.

Still, “Chips Ahoy!” has had a lasting impact on Finn’s betting habits.

“I always bet on the fifth horse in the sixth race,” said Finn, who in addition to annual Saratoga trips has attended the Kentucky Oaks. “Other than that, I’m a word guy and base my bets on the names of horses, which means I lose a lot.

“Nothing ever works out for me at the track, but I always feel like whatever I put into it I get out of it.”