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James Minchin III

It may not have been easy, but country star Jason Aldean has finally hit the big time.

How do you know you’ve made it?

Forgive Jason Aldean if he still asks himself that question. His path to country music superstardom hasn’t quite been as direct as he had imagined when he was spending summers learning to play guitar from songbooks. Back then, it seemed simple: Learn some Alabama songs, knock out a George Strait tune or two, get famous, end scene.

Watch Jason Aldean perform live at the 2011 CMT Music Awards, June 8 at 8 p.m. EDT, on CMT and online at CMT.com.

It did and it did not work out just like that for young Jason Aldine Williams. He played gigs in Florida (where his dad lived) and Georgia (where he lived during the school year with his mother) through high school. By 21, he’d signed with a label and moved to Nashville. It was just as he planned. Williams (stage name Jason Aldean) had made it.

That is until the label dropped him. He signed another contract but was dropped again. After six years in Nashville, Aldean was ready to give up — but he gave it one more shot with tiny Broken Bow Records. Within a year, he had a No. 1 hit, “Why,” and had been named the Country Music Association’s Top New Male Vocalist. Aldean had made it … again.
“Timing is everything,” the 34-year-old says now.

Following another brief moment of doubt when his second album, Relentless, stalled, his third effort — 2009’s Wide Open — hit big, producing three No. 1 hits. It was only then that Aldean admits, “I knew I was here to stay.” Now, in addition to earning him four CMT Music Award nominations and a slot performing at the June 8 ceremony, his latest album, My Kinda Party, has won him the chance to join the ranks of country music royalty.

“Growing up I learned to play on Alabama’s ‘My Home in Alabama’ and George Strait’s ‘The Cowboy Rides Away,’ and now I’m singing with Randy [Owen, of Alabama] at concerts and for George Strait at award shows,” Aldean says with a laugh. “And that’s intense. There are a lot of nerves in a CMT-style show, and you just don’t want to screw it up. You want to prove you’ve made it.”