Home Free, Tiffany and Me

An A Cappella Valentine's Shopping Spree

If I was in love with a country singer, all I’d want for Valentine’s Day is a song. One he was singing just for me. How romantic would that be?

Probably not romantic enough.

Which is how I happened to take these five country singers out shopping for V-Day gifts for their significant others.

Members of the a cappella band Home Free were in Chicago on Friday (Feb. 12) for a show, but first, we took to the swankiest parts of Michigan Avenue looking for some nice things — especially the kind in those little blue boxes — to bring home to their wives and girlfriends.

Austin Brown, the high tenor of the group, did most of the shopping. There was a gorgeous short Natori robe from Sak’s Fifth Avenue and a black onyx bracelet from Tiffany & Co. (Both for his lucky, lucky girlfriend Olena.)

But really, Valentine’s Day was just an excuse to shop, and shopping was just an excuse to talk about their music.

The band’s social media bio says they are “Five guys. Five microphones. And that’s it. The world’s first country vocal band.”

And while that may be true, they aren’t rookies.

The band came together seven albums ago, when baritone Chris Rupp and his brother Adam — the group’s beatboxer — put a group together for a talent show at their church, and things took off from there.

The Rupps’ band saw some comings and goings since those first years, but in 2008 Rob Lundquist (tenor lead) joined the group, with Tim Foust (vocal bass) coming on 2012 and Brown in 2013. Just in time for that TV win.

After winning NBC’s The Sing-Off in 2013, the group’s been taking their vocals on the road and building an incredibly loyal fan base in the process. Those two collided when their fans came to see them when they made their Grand Ole Opry debut late last year.

“Our fans just overwhelmed us,” Brown said. “They traveled from all over. They cheered so loud that it made us look so good to everyone there. It was more than we could ever hope for.”

And while we talked a little bit about what that TV win meant, with some fame and some fortune, what has mattered more than anything to the band is the fans who have their back.

Brown told me the story that sums up that loyalty.

“We were supposed to play The Tonight Show With Jimmy Fallon this past December, but our flight kept getting delayed and delayed,” he said.

Desperate to get to the show on time, they booked a private jet for $15,000, but even that didn’t get the guys there in time to perform.

But we still had a great time, got to hang out with Kenny Rogers, and Channing Tatum came in and said hi and introduced himself as ‘Chan.’”

Since the Home Free guys aren’t quite in the private-jet tax bracket yet, that was an expensive trip to wrap their heads around when it was all said and done. So their fans offered to pay them back. Within one hour of starting a Go Fund Me campaign, they reached their goal of $10,000. And within 24 hours, they’d raised more than $25,000.

The band’s most recent release, Country Evolution, is actually their seventh studio album since they started recording in 2007 and their third since winning The Sing-Off.

Alison makes her living loving country music. She's based in Chicago, but she's always leaving her heart in Nashville.