Woolsey was born on Feb. 15, 1944, in Houston. After graduating from Southwest Texas State University in 1969 with a BBA degree in business, Woolsey began working in Decca Records’ promotion department. He spent time working at several labels before relocating to Nashville in 1973, when he began serving as the head of promotions for ABC Records’ newly-launched country division. There, he helped guide the careers of Johnny Rodriguez, Jimmy Buffett, Billy “Crash” Craddock, Donna Fargo, Freddy Fender and the Amazing Rhythm Aces. Simultaneously, Woolsey and his then-wife Connie owned the San Marcos, Tex., club The Prairie Rose, where Woolsey first saw and became acquainted with Strait. He immediately recognized Strait’s talent and booked him at the venue as a regular performer.

Woolsey followed his success at ABC Records with an unprecedented run at MCA during the 1980s, bringing radio success for artists including Barbara Mandrell, Don Williams, Loretta Lynn, Tanya Tucker, Conway Twitty and the Oak Ridge Boys, all of whom would become members of the Country Music Hall of Fame.

In 1981, following the success of the John Travolta film Urban Cowboy and on the cusp of a new traditionalist movement, Woolsey convinced MCA Records head Jim Fogelsong to sign Strait to the label, where Strait remains to this day. On MCA, Strait released his debut single, “Unwound,” which had an undercurrent of Texas swing; the song reached No. 6 on Billboard‘s Hot Country Songs chart and launched Strait’s juggernaut career. In 1984, Woolsey left MCA and devoted himself to managing Strait’s career full-time.