Alan Poizner
Kristin Luna
December 10, 2014 10:00 AM

Brett Eldredge traded his country swagger for the smooth stylings of Frank Sinatra Tuesday night as he invited a small crowd of friends and family to come fly with him at an intimate event in Nashville.

Dressed to the nines in a tux and bow tie – the same one he sported for the CMA Awards last month, he told PEOPLE – Eldredge, 28, very much looked the part as he crooned nine songs backed by a seven-piece band in the recently re-opened speakeasy The Sutler saloon.

The 2014 CMA New Artist of the Year took the stage, explaining that for him the night was all about playing the music that inspires him. He then encouraged his guests, no more than 75 people, to drink up as he led into his first number. “The tab’s on us,” joked the Illinois native, who took his own words to heart as he sipped down a Jack and Coke or two.

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For the following hour, Eldredge worked his way through some of Sinatra’s biggest hits like “Fly Me to the Moon,” “Summer Wind” and “That’s Life.” And though he was certainly enjoying covering Sinatra, the musician clarified he’s no wedding singer – unless of course it’s at his own wedding in the future. Before launching into “The Way You Look Tonight,” the single Eldredge told the crowd, “I’m going to sing it to a special girl someday. Right now, though, I’m going to sing it to a lot of special girls!”

Eldredge closed the night with a familiar holiday tune, “The Christmas Song (Chestnuts Roasting on an Open Fire)” and told the crowd to “tell all your friends they missed something fun. We want to make this an annual event and grow it.” He then stuck around and mingled with guests – including his parents, who now live in Nashville, too.

“I’m absolutely thrilled to see him do this because he used to do this [style of music] when he was younger, but I haven’t heard him do it in a long time,” his mom Robin Eldredge told PEOPLE.

The musician said he does indeed plan on “An Evening with Brett Eldredge” becoming a regular event and that he hopes to add a philanthropic element to it.

“We’re going to grow this into something big and raise a bunch of money,” he told PEOPLE. “I hate seeing kids fight for their life when they should have a lot of life ahead of them, and I’m already working on my own charity for childhood cancer,” he said. “I want to help out in every way possible and help kids have a chance at life. I want to bring some dollars and let them have a chance to live.

“The best part of my job, by far,” he continued, “is being able to get in the spotlight and raise awareness for something that really matters more than anything.”

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