Erv Woolsey, legendary country music executive and manager, dead at 80

Erv Woolsey, a country music executive, talent manager, and Nashville entertainment entrepreneur, has died at the age of 80.

Among many acts he worked with and notable successes attributed to his name, the four-plus decades of friendship and guidance he offered to Country Music Hall of Famer George Strait are most prominent.

"My manager for around 45 years and most importantly, my friend for even longer, Erv Woolsey, passed away this morning," Strait wrote in a statement. "He had complications from a surgery and just couldn't overcome it. He was a very tough man and fought hard, but sadly it was just too much. We will miss him so very much and will never forget all the time we had together. Won't ever be the same without him."

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 he is preceded in death by his parents, John and Mavis Woolsey, and brother Johnny Woolsey. Details on arrangements will be shared at a future date.

A star-studded era

Woolsey, a record promoter in Houston and Nashville for Decca, ABC and MCA Records, respectively, was also a manager of San Marcos, Texas' Prairie Rose.

Woolsey's career before working with Strait was impressive.

After graduating from Southwest Texas State University in 1969 with a bachelor's degree in business, Woosley, as the head of promotions for ABC Records' country division, advanced the radio-friendly careers of artists including Johnny Rodriguez, Jimmy Buffett, Billy "Crash" Craddock, Donna Fargo, Freddy Fender, and the Amazing Rhythm Aces.

Moving to MCA Records, Woolsey's work allowed eventual Country Music Hall of Famers Barbara Mandrell, Don Williams, Loretta Lynn, Tanya Tucker, Conway Twitty, and The Oak Ridge Boys to maintain stardom.

Impressed by Strait's Western swing-inspired stylings, Woolsey persuaded then MCA Records label chief Jim Fogelsong to sign the Poteet, Texas native to a recording deal. Had he not signed to MCA, Strait, who had already made many unsuccessful trips to Nashville, -- as he has frequently noted -- would've taken a job designing cattle pens instead of singing anthemic country songs.

Woolsey's ear and Strait's skill were undeniable.

Six months after being signed, Strait's single, "Unwound" was a top-10 hit.

In a 1987 UPI interview, Strait recalls that it took 13 months for him, while managed by Woolsey, to achieve a long-desired gold record and the first of 61 chart-topping singles via 1982's "Fool Hearted Memory."

Woolsey guides multiple commercial booms, genre expansion

By 1984, Woolsey had permanently left bar management and record promotion to devote himself entirely to managing Strait's career.

A year later, Woolsey co-wrote "In Too Deep" on Strait's platinum-selling and chart-topping album "Something Special." Also, by 1987—nearly two greatest hits compilations, 18 top-ten hits, and 15 million albums sold into Strait's less than a decade-long career—Woolsey's guidance of Strait's career aided him in selling nearly 100,000 tickets for a pair of concert dates at Houston's Astrodome.

"The swinging roots of country music are [in the nation's] blood," stated Strait.

"Country music tells stories that are real and are real to some people -- they've experienced them," he said. "I don't think a lot of rock music is that way. It's more music than lyric content. In country music the lyric content is more important."

By the 1990s, Strait's popularity hadn't waned and his partnership with Woolsey deepened.

In 1992, concert promoter and film producer Jerry Weintraub (Robert Altman's "Nashville," Barry Levinson's "Diner," and "The Karate Kid" film series) and Woolsey persuaded the "All My Exes Live In Texas" vocalist to portray a leading character essentially styled after himself in the motion picture Pure Country.

The film grossed over $15 million at the box office.

Three years later, via his George Strait Country Festival Tours, Strait and Woolsey maintained the former's stadium-sized appeal.

All throughout the years, acts alongside Strait also benefitted from Woolsey's guidance in management, including Clay Walker and LeeAnn Womack, plus Dierks Bentley and Ronnie Milsap.

The George Strait Country Festival Tours also saw acts including Alan Jackson, The Chicks, Tim McGraw, Faith Hill, Kenny Chesney, Womack, and Western swing band Asleep at the Wheel appear on its stages.

A decade into that tour's existence, it was grossing $66 million yearly and McGraw noted in a CMT interview that the event's fans were "all there to have fun [and were] primed up, ready to go and [ready] to turn it loose."

Strait's commercial success was also still intertwined with Woolsey's craftsmanship.

The manager wrote on Strait's signature No. 1, "I Can Still Make Cheyenne," which appeared on the 1996 Country Music Association Album of the Year, "Blue Clear Sky."

In 2023, the single received a BMI Million-Air Award for over one million spins on terrestrial radio.

Staying true to himself

By the 2000s, Woolsey had achieved a peerless reputation as a talent manager. In 2006, the Nashville Association of Talent Directors celebrated him at the International Entertainment Buyers Association conference.

He remained undeterred in all entrepreneurial facets of his life.

Four years prior, his interests in talent and country culture development moved into the nightlife realm as, alongside business partner Steve Ford, in 2002, he developed The Trap, a downtown Nashville country bar across the street from Nissan Stadium. Later, the Music Row dive bar concepts Losers, Winners, and the Dawg House—meant to attract country music fans, blue-collar workers, and Nashville's re-emergent downtown white-collar partiers alike—opened.

By 2016, Losers had opened an outpost at Las Vegas' MGM Grand Hotel.

Woolsey had also been involved in the buying, training, and selling of thoroughbred racehorses for three decades (and was a lifetime member of the Texas Thoroughbred Association). In 2021, he saw Super Stock, a horse he and his partners purchased in 2019, compete in the Kentucky Derby.

In later years, Woolsey served on the Board of Directors for the Country Music Association and the Tennessee Museum of History. He also remained in artist management. He worked with acts including Ian Munsick, Davisson Brothers Band, Kylie Frey, Triston Marez, Nick Davisson, Zach Neil, Stone Senate and Vince Herman while mentoring young managers, agents, artists, and executives.

A note from Country Music Hall of Fame and Museum CEO Kyle Young sums up Woolsey's career.

"Without the savvy and determination of Erv Woolsey, we may never have heard of George Strait," Yound wrote. "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."

This article originally appeared on Nashville Tennessean: Erv Woolsey, legendary country music executive and manager, dead at 80