Sara Kauss, WireImage
"I played bars with my dad since I was 12, three to five nights a week with my brother," the 44-year-old recalls. "I was offered my first record deal when I was 15 ... [my dad] had to co-sign it, and he wouldn't co-sign it. He used to have this thing, 'You need to play for the people that love you and the people that hate you, and the people that couldn't care less.' I don't think I really realized what that meant, but I do know when I felt like I was ready to have a contract."
The singer-songwriter remembers that iconic moment when his father made that same realization. "I was probably 23 when he was watching me in a bar, and he goes, 'You're ready now," Gary recounts. "I realized when he said that, that I didn't have to think about how I sing a song. You give me a song and I was going to sing it and that's the way it was going to be with my band. Where earlier, I would imitate and try to find something that's cool. So I think I really became myself in that bar."
The "Every Storm (Runs Out of Rain)" singer admits his career hasn't been smooth sailing since his first record, Used Heart for Sale, was released in 1996. However, with eight studio albums and 21 Top 40 singles to his credit, he does have some sage words for others who hope to follow in his footsteps.
"I would say never quit," Gary shares. "You have to wait until your time comes. Nobody's ever the flavor of the week very long, and you just have to keep doing it."
Gary also makes sure he surrounds himself with talented musicians. "Especially now, with all the karaoke and contests and stuff, I think it's important to have a band," he explains. "It's really important to get in there and cut your chops in front of people, and learn how to control an audience and how to entertain."
His new album, Set You Free, will be released in early 2013. He will spend much of the next few months on the road in support of the upcoming CD. Follow his schedule here.