Tritt worked at a furniture store, and later as a supermarket clerk. He lived with his mother after she and his father divorced; they remarried when he was 18. He worked at an air conditioning company while playing in clubs, but gave up the air conditioning job at the suggestion of one of his bandmates. Tritt's father thought that he would not find success as a musician, while his mother thought that he should perform Christian music instead of country. Through the assistance of Warner Bros. Records executive Danny Davenport, Tritt began recording demos. The two worked together for the next several years, eventually putting together a demo album called Proud of the Country. Davenport sent the demo to Warner Bros. representatives in Los Angeles, who in turn sent the demo to their Nashville division, which signed Tritt in 1987. Davenport also helped Tritt find a talent manager, Ken Kragen. At first, Kragen was not interested in taking an "entry-level act", but decided to sign on as Tritt's manager after Kragen's wife convinced him. Musical career 1989–1991: Country Club Tritt's contract with Warner Bros. meant that he was signed to record six songs, and three of them would be released as singles. According to the contract, he would not be signed on for a full album unless one of the three singles became a hit. His first single was "Country Club". Recorded in late 1988 and released on August 7, 1989, the song spent 26 weeks on the Hot Country Singles & Tracks charts, peaking at number nine. It was the title track to his 1990 debut album Country Club, produced by Gregg Brown. The month of its release, Tritt burst a blood vessel on his vocal cords, and had to take vocal rest for a month. Second single "Help Me Hold On" became his first number one single in 1990. The album's third and fifth singles, "I'm Gonna Be Somebody" and "Drift Off to Dream", respectively peaked at numbers two and three on the Hot Country Singles & Tracks charts, and number one on the Canadian RPM country charts; "I'm Gonna Be Somebody" also went to number one on the U.S. country singles charts published by Radio & Records. "Put Some Drive in Your Country", which was released fourth, peaked at 28 on Hot Country Songs. Country Club was certified platinum by the Recording Industry Association of America (RIAA)