One of the most interesting and accomplished characters to ever grace the history of country music has unfortunately passed away. Eddie Pleasant just about did it all. He was a performer and musician. He wrote songs. He worked as the business manager and right-hand man for Hank Williams Jr. for 24 years. And he’s credited for being one of the first ever to sell T-shirts as part of the music business. For half a century, Eddie Pleasant influenced the country music business in immeasurable ways.
It’s hard to know where to commence enumerating Eddie Pleasant’s country music contributions, since they were so vast and diverse. If you start at the beginning, he got into the business as a performer, playing at places like The Cottage Inn and Double Eagle bar in Waco in the 60s. Born in Wells, TX, June 3rd, 1927, Eddie moved to Freeport, TX when he was 16-years-old. His uncle worked at Dow Chemical and got him a job there before Eddie moved on to Waco and worked at a textile mill for 17 years, playing beer joints at night. This is where he would rub elbows with Willie Nelson who was from nearby Abbott. When Willie moved to Nashville, so did Eddie in 1968.
Eddie Pleasant’s first job was playing drums for Wilma Lee and Stoney Cooper, who at the time were opening for Hank Williams Jr. While playing, Hank Jr. would sneak behind Eddie on stage and tell him a dirty joke in his ear. This would throw off Eddie’s timing, nearly train wrecking the song, and Hank Jr. would have a hoot over it. The two became close friends, and Hank Jr. hired him on as his close personal assistant and business manager.
At the time, Eddie Pleasant was also engaged in one of his favorite and most lasting contributions to country music: songwriting. Some of the important songs Eddie Pleasant wrote include:
Jim Reeves – “Lonesome Waltz”
Faron Young – “Gettin’ Soft on You”
Lefty Frizzell – “When The Rooster Leaves the Yard”
Kitty Wells – “Jesus Loved The Devil Out of Me”
Hank Williams III – “Devil’s Daughter”
Hank Williams Jr. – “My Hometown Circle R”
Hank Williams Jr. – “Richmond Valley Breeze”
Hank Williams Jr. – “Your Love’s One Thing (I Ain’t Forgot)”
Hank Williams Jr. – “Removing The Shadow” (with Lois Johnson)
But if you talk to some in the music business, they know Eddie Pleasant for one thing and one thing only: selling T-shirts. Though it may seem like a commonplace function of the music business today, before Eddie Pleasant, it just wasn’t a focus of either artists or the public.
Eddie Pleasant began working for Hank Williams Jr. right about the time the legendary promoter and manager Buddy Lee came into the picture. Buddy Lee was a wrestler that moved to Nashville and became a booking agent in the late 50’s. Buddy Lee also came up with the idea of putting concert dates and a picture of the artist on a white undershirt and selling them at concerts. Soon all the country music artists, and eventually artists from every genre of popular music adopted the newfound revenue stream, but Eddie Pleasant is regarded as the first to actually sell concert T-shirt’s to the public, and sell them he did.
“See everybody was doing at the end of the show as a hobby,” Eddie Pleasant told Saving Country Music back in 2017. “Buddy Lee wanted to sell them before the show, and during the intermission. I would get up on stage. Man, I was as much of an act as the rest of them. I could really plug them T-shirts. You’ve ever heard auctioneers auction stuff off? I was a pretty good auctioneer. We made it a business instead of a hobby.”
“There were stories where he would come off the road and he would have all this money in black Hefty garbage bags that had never even been folded or counted,” says CJ Udeen, a Nashville-based steel guitar player whose been caring for Eddie over the last few years. “Then it would get dumped out over tables to get counted. One time when they pulled into Hendersonville at A1 Diesel, a guy came to clean the bus and he grabbed these two large black Hefty trash bags, and the guy was like, ‘Is this garbage?’ and Eddie was like ‘No, that’s money!’ That’s kind of how he ran business.”
Through selling T-shirts, his management pay from Hank Jr., and his songwriting royalties, Eddie Pleasant became quite a wealthy man. There were shows where T-shirt sales alone would pull in $100,000—an astronomical figure at the time. “I owned five houses in town,” Eddie said. “I owned land in Texas, a ranch in Dixon [Tennessee]. Back then I owned my own recording studio in Hendersonville at 111 Stadium Drive. I had a 30-acre quarter horse ranch with 48 head of registered quarter horses.”
Eddie was also a character as you can imagine, and according to most everyone who knew him, a kind heart.
“L.E. White was a side guy for Conway Twitty. He was in foreclosure, and he needed money to stay in his house,” explains CJ Udeen. “The story goes he came home from church one Sunday, and there was this pile of money that’s just crumpled like Eddie used to keep it, laying across his coffee table in his living room. It was enough to save his house, around $10,000. That’s just one of many Eddie Pleasant stories of him helping people out.”
With how successful Eddie Pleasant became, other artists tried to hire him away from the Hank Jr. operation, including Reba McEntire and Garth Brooks. But Eddie Pleasant stayed loyal to Hank Jr. and continued to work with him until Hank married his fourth wife, Mary Jane Thomas. Eddie Pleasant was a significant part of the entourage that hung around Hank Jr. at the time, and Mary was worried it was a little too wild. And so along with others in the Hank Jr.’s crew, Eddie Pleasant was fired.
However, it didn’t take long for Eddie Pleasant to find a new gig working for Hank Jr.’s son, Hank Williams III. In 1996 when Hank3 started out, he hired some of the crew Hank Jr. let go, including Eddie Pleasant, tour manager Big Al Halterman, and fiddle player Vernon Derrick. Eddie Pleasant would set up at Hank3 shows with a 1940’s amplifier and a microphone, and hawk T-shirts like a carnival barker. Similar to what happened with Hank Jr., Eddie Pleasant became a part of the show.
But as Pleasant got older and couldn’t carry boxes of T-shirts, he began to fall on hard times. Though he could make a lot of money, he was never especially good with it. Since 2017, steel guitar player CJ Undeen has been Eddie’s default caretaker. Meeting Pleasant when they both toured with Hank3, Undeen now performs with Gary Allan and others.
“He never drank, never smoked, never cussed,” CJ Udeen explains. “And it’s kind of amazing that he was ever allowed to handle money, let alone millions of dollars, because he never really had that skill set.”
But even after he was no longer capable of selling T-shirts or tour managing, Eddie Pleasant continued to try and write songs, and pitch them to artists. It was his undying passion. Even into his 90s, Eddie became a staple at the reception desks of major label offices and publishing houses on Music Row, trying to sell songs that were more suitable for the 60s. Despite the incessant failures, Pleasant still tried to write and sell the next big hit. “I’ve got 5,000 songs,” Pleasant told Saving Country Music in 2017. “I fool with them every day.”
After profiling Eddie Pleasant, he would also regularly call Saving Country Music headquarters, seeing if there any artists in Austin who may want to record his songs.
Eddie Pleasant led an extraordinary life as one of the most unique and interesting characters to ever grace the country music business. You won’t see him in the Country Music Hall of Fame, or find his music on Spotify. But he left his mark in many varied ways that still influence country music today.
Eddie Pleasant was 95.