No wedding band worth its salt shows up without a couple of Sinatra tunes in tow. But when a local wedding outfit called The Shakedown presents an all-Sinatra evening on Saturday to honor the 100th anniversary of the singer’s birth, the act will land far beyond what most wedding bands ever aim to achieve.

In 2009, while studying at UNC-Chapel Hill, Nash Roberts cobbled together a five-piece band devoted to soul and R&B covers, and The Shakedown was born. During the next few years, the group established a foothold at frat parties before graduating to weddings. Still, the requisite bar gigs started to grate on Nash.

“I thought, ‘This band is not a bar band,’” he explains. “‘We can do something interesting.’”

So Roberts set his sights on musical tributes to figures who, while well-known, were not as ubiquitous on stages as numerous “over-tributed” acts like AC/DC. The Shakedown dedicated evenings to Sam Cooke and Van Morrison. Roberts grew the sound, adding horns and percussion and tapping local singers like Tamisha Waden of The Foreign Exchange and Jeanne Jolly and members of Peter Lamb & the Wolves and Orquesta GarDel.

In advance of the Sinatra show, I spoke with him about the big gig.

INDY: The Shakedown has done tributes to Van Morrison and Sam Cooke, but Sinatra would seem to be an even greater challenge. If you fail at Sinatra, you sound like Bill Murray’s lounge singer.

NASH ROBERTS: I spent the past two weeks freaking out about it. And part of that was because [normally] there might be a modulation up to a half step or a whole step, but for the most part you’re in one key the whole time. But we’re sitting down and playing these songs, and in “Luck Be a Lady,” that song changes keys four times just in the intro, and the whole song is moving in different keys throughout. I’m not a classically trained singer. My grandmother was—Jackie Roberts, inducted in the Kentucky Music Hall of Fame, incredible singer from the classical tradition. My brother—Clint, amazing singer—trained under my grandmother. Me, I went my own route, the way I’ve always done it: frat parties, bar gigs, weddings, etc. This is the first time where it’s a tall order and you really have to walk the tightrope and really know the songs because, as you say, it can become so shtick-y, very quickly.

So what was your reaction to the suggestion of doing a Sinatra tribute?

I didn’t really see the wisdom until I sat down and listened to the Live at the Sands album. Of course I knew the music, but I didn’t know how amazing it is in a live setting. All the music is arranged by Quincy Jones. It’s the Count Basie Orchestra; there’s probably 35 musicians in the band. So that was the album where I was like, “Oh my God, we gotta do it.” We’re not gonna be able to do it like this, but we’re gonna try to get as close as we can.

At the same time, I’m not a Frank Sinatra impersonator. One, that’s not of interest to me, and two, I don’t think I can do it. Frank started with the Tommy Dorsey Orchestra. Tommy Dorsey was a prodigy trombone player, and so that’s where he got a lot of his vocal phrasing from, and you can really hear it. The deeper, brassytone to his voice, which is so signature to Sinatra’s music, I don’t have the ability to do these huge finishes, where he’s holding a note, in vibrato, for like 15 seconds. And I think people will understand that.

That’s a lot of preparation for one evening of music.

A big part of the show’s success will be Kenan MacKenzie, who is our saxophone player and has been for many years. While I’ve been listening to these songs and singing them, he’s written out six-part horn charts for all the songs, which is an extremely lengthy process. It’s a testament to how excited he is about this and how much it means to him. Most of these songs we’ll never play again. We might add a few of them to the wedding set list, but it’s a fleeting moment in time. You try to get them right for this big night, and then you move on.

What was in your mind when you put the set list together?

The song selection was an iterative process between me and Kenan. Kenan is going to sit down and spend six hours writing out each chart, so if this song isn’t going to pop anyway, why do it? We try to be educated on the front end. And the other thing is, I’ve got to be excited about singing the song, selfishly. Like, “I’ve Got You Under My Skin,” I cannot wait to sing that song. I’ve got goose bumps right now thinking about that recording, just hearing it in my head.