Iconic artist manager, record promotion executive, creative advocate and innovator Eugene Ervine “Erv” Woolsey passed peacefully Wednesday morning in Clearwater, Florida. Under doctors’ care due to complications from surgery, the Texas-born, longtime Nashville resident changed the face of modern country music through his stewardship of Country Music Hall of Fame member George Strait’s career, as well as progressive traditionalists Lee Ann Womack, Dierks Bentley, classic Texan Clay Walker and groundbreaker/Country Music Hall of Famer Ronnie Milsap.
Born February 15, 1944 in Houston, Texas, Woolsey spent his entire professional life in the music business. After graduating from Southwest Texas State University in 1969 with a bachelor’s degree in business, Woolsey went to work in the promotion department at Decca Records. He spent time at several record labels before moving to Nashville in 1973 as the head of promotions for ABC Records’ newly-opened Country division where he elevated the careers of Johnny Rodriguez, Jimmy Buffett, Billy “Crash” Craddock, Donna Fargo, Freddy Fender and the Amazing Rhythm Aces.
At the same time, Woolsey and his then wife Connie owned The Prairie Rose, a club in San Marcos, Texas. It was there he first saw and met George Strait; recognizing something in the classic Texan’s approach that stood out, Woolsey booked Strait regularly to perform.
Woolsey followed a string of successes at ABC with an unprecedented run at MCA during the ‘80s. Creating ongoing radio success for future Country Music Hall of Fame members Barbara Mandrell, Don Williams, Loretta Lynn, Tanya Tucker, Conway Twitty and The Oak Ridge Boys, as well as powerhouse vocalist Lee Greenwood.
In 1981, in the wake of “Urban Cowboy” and on the verge of a new traditionalist movement, Woolsey convinced label head Jim Foglesong to sign Strait to a recording deal at MCA Records, his label home to this day. “Unwound,” Strait’s debut single, embraced a Texas swing undertow, went to #6 on Billboard’s Hot Country Songs chart, and a storied superstar career in music was underway.
In 1984, Woolsey left MCA to devote himself full-time to managing Strait’s career. Along the way, the elegant performer would win Entertainer of the Year Awards across four decades, as he and his manager broke ground with 1992’s Jerry Weintraub-produced major motion picture “Pure Country,” which captured Strait’s larger than life charisma, and the stadium-sized George Strait Country Festival Tours, starting in 1995, which showed that country music could attract Rolling Stones’ sized audiences across America and featured Alan Jackson, The Chicks, Tim McGraw, Faith Hill, a young Kenny Chesney, Womack and Texas’ favorite Western swing band Asleep at the Wheel.
Strait has continued his stadium-selling ways. After retiring from traditional touring, he is still playing a handful of stadiums across America each year; most recently sharing his stage and audience with multiple-Grammy winners Chris Stapleton and Little Big Town.
With a strong commitment to authenticity and protecting his artists’ integrity, while creating broad spectrum opportunities, Woolsey ultimately signed Lee Ann Womack, Dierks Bentley, Clay Walker and Ronnie Milsap, all seeking a manager who believed in space for an individual sound and an audience who saw their lives in each artist’s songs.
That deep love and respect for creative people spawned an offshoot outlet as a songwriter. Not only did Woolsey co-write “In Too Deep” on Strait’s 1985 Something Special, he was a writer on Strait’s signature No. 1 “I Can Still Make Cheyenne” on the 1996 Country Music Association Album of the Year Blue Clear Sky. “Cheyenne” received a coveted BMI Million-Air Award for over one million spins on terrestrial radio.
Indeed, his love of songwriters, pickers and artists at all stages of their career inspired his developing a series of clubs, bars and hangs out. Alongside business partner Steve Ford, he opened The Trap, across from the former Adelphia Stadium, home of Nashville’s NFL team, the Titans, before striking pure gold with the anti-glam, come-as-you-are Losers. Designed as a hole in the wall for publishers, producers, writers and the alternative Music Row types, Losers’ success spawned the equally busy Winners, right next door, and the Dawg House.
It was that love of life, good times, music, friends and the neighborhood bar sense of classic Nashville that informed Woolsey’s business decisions. His continued love of the business and developing new talent saw him signing emerging artists Ian Munsick, Davisson Brothers Band, Kylie Frey, Triston Marez, Nick Davisson, Zach Neil, Stone Senate and Vince Herman over the last few years.
Woolsey served on the Board of Directors for the Country Music Association, as well as the Tennessee Museum of History. A frequent counsel to young managers, agents, artists and executives, he was a gracious industry leader who was generous with his knowledge and time.
A longtime fan and passionate member of the horse racing community, Woolsey is a Lifetime Member of the Texas Thoroughbred Association. He was also regular at Kentucky’s Churchill Downs and Keeneland, including Super Stock’s run in the Kentucky Derby Grade 1 in 2021 and Jordan’s Henny in the Kentucky Oaks Grade 1 in 2017.
Woolsey passed peacefully under the care of physicians in Clearwater, Florida on Wednesday, March 20, 2024 following complications from surgery. He is survived by his son Clint, ex-wife Connie, brother David and sister Beth, and preceded in death by his parents, John and Mavis Woolsey, and brother Johnny Woolsey.
The Country Music Hall of Fame remembered Erv Woosley, ”Without the savvy and determination of Erv Woolsey, we may never have heard of George Strait,” said Kyle Young, CEO of the Country Music Hall of Fame and Museum. “Erv heard Strait in a Texas bar in 1975 and was an immediate fan and proponent, when others said the singer sounded too traditional. Later, as an MCA Records exec, Erv pushed the label to sign Strait in 1981. And when execs urged Strait to change his image and his sound, Erv as his manager backed Strait’s determination to stay true to himself. You know the rest. Strait became a superstar who filled stadiums, and together Strait and Erv helped lead country music back to its traditions. All of us owe Erv Woolsey an enormous debt of gratitude for leading with his convictions and always supporting artists and new talent.”
