Workin' On It, Adam's sophomore record, is due out tomorrow, the same day as the Edmonton teen's Stampede show on the Coca-Cola Stage.
"This CD is a lot more to do with love. It's a big word nowadays. Everybody knows that word," says Gregory about the more mature subject matter on Workin' On It.
"I hope people can listen to this music and relate their life experiences to it. That's what I try to get through in my music."
But Adam, surely you haven't called anyone babe in your life, as you do on the album?
"No, not yet -- one day. Hopefully, I get to experience it all one day."
Gregory says he doesn't find singing about things he hasn't experienced difficult, as long as it is a good song.
Speaking of good songs, Gregory has co-written two on the album -- Walking and Memory Like That -- as well as picked up some from more experienced writers such as Garth Brooks. (Sweet Memories is a ballad Brooks wrote a few years back.)
"We have, like, 50/50 with Sony," Gregory says about song selection. "So, we pick the songs we like and they pick the songs they like and usually we're on the same field as they are."
When I Leave This House is one such song. The edgy song was co-written by Tom Wilson and Colin James.
"I think it's a real cool song and it's one of my Auntie's favourite songs. It's different than anything I've done before."
Billy Ray Cyrus sings on the track with Gregory.
"I met Billy Ray Cyrus at the Big Valley Jamboree (in Camrose) last year. He invited me up on stage and I sang Achy Breaky Heart with him.
"He gave me his number and I called him and kept in touch," Gregory says of the unlikely pairing.
The easy-going singer says there is one type of song he refuses to do.
"I've been presented songs about beer and getting drunk. I won't do those songs, no way! Because you don't have to drink to have a good time."
That's a good lesson for the teen to learn, especially now that he's combining life on the road with attending high school in Edmonton.
"It gets more difficult at the end of the year because of final exams, but I keep a grasp of it. Teachers understand my touring schedule and stuff," says Gregory, who adds that his fellow students are also supportive.
"Being on the road, I've definitely grown up as a person. I've learned good life lessons on the road. The business can be tough but we keep it fun.
"You learn stuff on the road you can't learn in school."
Canada's geography is far more clear for one thing -- there's no better way to understand a country than to drive across it.
"I'm also learning how to meet people."
His career is also allowing Gregory to bank some money and employ his older sister -- she sells his merchandise.
So, is providing a paycheque to your older sister a bit weird for a 16 year old?
"No, I don't expect her to do it for nothing.
"My family has always been there for me. They're the best a boy could have. That love -- they bring that love to me all the time and they're 100 percent supportive of my music."
It's also their influence that helps him keep his cowboy boot-wearin' feet on the ground.
"I've promised people throughout my life that I won't let it go to my head. And I don't break promises. Well, I try not to. But this one I'll never break for sure."