Growing up in the rural working class community of Tillamook, Oregon, with Merle Haggard fans for parents, perhaps it was inevitable that Jerry Kilgore would hear the call of country music early on. Kilgore’s grandmother gave him his first guitar when he was just twelve years old, but it was an experience when he was eighteen that changed the course of his life. “Back in 1986, I went to see George Strait at a huge honky tonk called the Flower Drum,” Jerry recalls. “I was underage, but my parents got me in, and I was mesmerized by him. Not long after that, I was fronting a five-piece band I had put together. We soon became the house band at the Flower Drum, where George had played."

Kilgore’s course was set. He spent the next several years working the club scene playing classic country, first in Oregon, then in Phoenix, where a romantic breakup first inspired him to try his hand at writing his own songs. Soon Kilgore’s original songs were getting more requests at his shows than his covers. Jerry then spent two more years honing his chops in North Carolina before deciding to take a shot at Nashville. The young musician dragged his possessions into the yard and put a For Sale sign out, and the next day he loaded whatever hadn’t sold into his pickup truck and headed out for Music City.

Within a few short years Kilgore began to have success as a songwriter, penning “Love Lessons” for Tracy Byrd, “Leavin’ Comin’ On” for Mark Wills, “Cover You in Kisses” for John Michael Montgomery, and “If A Man Ain’t Thinking About His Woman” for Clay Walker. Kilgore’s songs caught the attention of powerhouse country producer Scott Hendricks, who had produced Alan Jackson, Faith Hill, and Brooks and Dunn among many others. Hendricks was President of Virgin Records’ new Nashville office at that time. “He came out to a club and saw me play,” Kilgore says, “and a week later he offered me a record deal on Virgin Records as the first male artist that they were signing.”