Hefty Bags Full of Cash & Hard Won Memories: The Story of Eddie Pleasant


“When I first moved to Nashville in 1996 my first gig was with Hank3,” explains CJ Udeen, a pedal steel player who now tours regularly with Gary Allan. “I got on the tour bus, and everyone’s new and there’s these five or six young guys that are all in our 20’s, and then there’s these three old guys. When we first got on the bus, it was real quiet and nobody really knew anybody. And Eddie Pleasant got on the bus and he looked at everybody, especially all these young kids and he said, ‘Well who’s the steel player?’ And I quietly raised my hand and said, ‘I’m the steel player.’ And he looked at me with the most disgusting look and said, ‘Oh my God, we should have gotten Don Helms!’ And I thought, ‘I hate this guy’.”

But that hatred wouldn’t last long. Like all of the people who have come in contact with Eddie Pleasant over the years—or as some refer to him as, “Shuckins,”—they seem to fall in love with him, his stories, his pure heart, and what he’s done for country music throughout the years, though mostly behind-the scenes.

The 89-year-old Eddie Pleasant currently resides in an apartment in Hendersonville, Tennessee, just north and east of Nashville with his wife of 38 years, and two grandchildren. In this humble setting, Pleasant still works at his desk every day surrounded by photos of him with Hank Williams Jr., Willie Nelson, Wilma Lee and Stoney Cooper, a young Hank Williams III, and others. And he writes songs. “I’ve got 5,000 songs,” Pleasant says. “I fool with them every day.” He’s even had the privilege to see some of them published and recorded by country music royalty, including Jim Reeves, Kitty Wells, Lefty Frizzell, and Hank Williams Jr.

But Eddie Pleasant isn’t known by the insiders and oldtimers of Nashville primarily as a songwriter. He’s known as one of the first, or possibly the very first individual to ever sell a concert T-shirt—meaning a shirt with an artist’s photo on the front, and dates of a tour on the back. Eddie Pleasant is know for being Hank Williams Jr.’s right hand man for 24 years, and in that time racking up a lifetime’s worth of road stories. He’s known for turning country music concessions from a side hobby to a six figure business, and bringing in so much cash he had to haul it around in Hefty garbage bags. He’s known by some as being almost like a country music version of Forrest Gump, where he inexplicably saw some of the key moments in country music history unfold right before his very eyes. And Eddie Pleasant is known for having one of the biggest hearts in all of country music.

Eddile Pleasant with Bobbie Nelson and Willie Nelson
Eddile Pleasant with Bobbie Nelson and Willie Nelson

“He was a songwriter through the 50’s and 60’s, and when Hank Jr. was 17-years-old, Eddie became Hank Jr.’s right hand man where he would do everything for him for 24 years,” explains CJ Udeen. Though it has been years since CJ and Eddie Pleasant traveled together on that first Hank3 tour, the two have remained close friends.

“It evolved to being the merchandise guy for Hank Jr., but for the first 10 years, it was just Hank Jr. and Eddie. And then obviously Hank Jr. hit and superstardom set in, and Eddie became merchandise manager until about 1990.”

Eddie Pleasant’s music career started back in Texas where he was born and raised, and for a short period he was a running buddy of Willie Nelson’s when both Willie and Eddie were still young and unknown.

“I was born in Wells, TX, June 3rd, 1927, on a Wednesday,” Eddie says proudly. Even at 89-years-old, when he talks about his personal history, Eddie is full of vitality and enthusiasm. “My mamma got married at 14. She was 25 before I was born. Her mother is Sarah Presley from Tupelo, Mississippi, who was related to Elvis. I was raised on a 25-acre cotton farm, and I moved to Freeport, TX when I was 16-years-old. My uncle was working at Dow Chemical, and I washed dishes at a restaurant until I could get on at Dow Chemical. I moved to Waco and worked at a textile mill for 17 years. I had a band the whole time at the Cottage Inn, and we also played the Double Eagle bar. Willie Nelson worked that county line back when we were both about 20-years-old. He lived in Abbott. Abbot is 17 miles from Waco. We played them county lines where there wasn’t no law. They’d get drunk and fight, and we’d have to grab our guitars and run!”

Eddie Pleasant on the far right with Wilma Lee and Stoney Cooper.
Eddie Pleasant on the far right with Wilma Lee and Stoney Cooper.

And run they did. Eventually Willie Nelson would move to Nashville, and in 1968, Eddie Pleasant followed him. He got his start as a drummer behind one of Nashville’s prominent acts of the time.

“I somehow got on playing drums for Wilma Lee and Stoney Cooper, and they opened for Hank Jr.,” explains Pleasant. “And Hank Jr. would come backstage and say something to me, and I would get off beat on them drums and couldn’t get back on, and Hank would just laugh.”

This was before Hank Jr.’s fall off of Ajax Mountain; before the beard and shades. Others who recall Pleasant’s early days in Nashville remember him constantly trying to pitch artists songs he wrote, including while he was supposed to be playing drums for Wilma Lee and Stoney Cooper. A star would walk by, and Eddie would completely forget his drumming duties and start pitching. Some of them took the bait.

A few of the songs Eddie Pleasant wrote and were eventually recorded and released 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) “…which meant he was removing his first wife to get to his second wife Gwen—Hank3’s mother,” Eddie explains. “Hank Jr. has been married for times and I was with him for all four wives.”

After Hank Jr. hired Eddie Pleasant away from Wilma Lee and Stoney Cooper, Eddie became Hank Jr.’s personal manager and close assistant. This led him to the merchandise business that would make Eddie famous in country music.

Eddie Pleasant with Hank Williams III
Eddie Pleasant with Hank Williams III

“When Hank3 started in about 1996 and put his touring band together, he basically took a bunch of guys that had been fired from his dad,” explains CJ Udeen. “Shelton [Hank3] kind of had a chip on his shoulder about Hank Jr., and a combination of being close to the guys when he grew up, and a way to put some of these guys back to work, and to kind of stick it to the old man so to speak, he hired Eddie Pleasant, he hired one of Hank Jr.’s tour managers named Big Al Halterman, and he hired Hank Jr.’s fiddle player from the Bama band Vernon Derrick. So Hank3 had a young band, but he had all of these oldtimers with him.”

“Eddie would sit behind the merchandise booth with a 1940’s Fender amplifier, and he would talk into a microphone and pitch the merchandise,” CJ Udeen continues. “I had never seen anything like it in my life. And as I got to know him and the character of him, I just though he was one of the biggest characters in Nashville. And people loved him.”

Eddie Pleasant got involved with 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 says. “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.”

Eddie-pleasant-1Eddie Pleasant took white T-shirts with an 8X10 picture of Hank Jr. on the front, and turned it into one of the most lucrative industries in music at the time.

“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. “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.”

Eddie Pleasant hit the big time selling T-shirt’s for Hank Jr. and Buddy Lee, and along with his songwriting royalties, began to amass a small fortune for himself in Hendersonville. “I owned five houses in town,” Eddie says. “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 Pleasant still has stationary and business cards from when he owned his working quarter horse ranch, and a working studio in Hendersonville. During the height of his run with Hank Jr., he was living high on the hog, and was willing to spread the wealth around.

“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.”

eddie-pleasant-2Pleasant’s T-shirts sales numbers also garnered him the attention of other artists. At the peak, he claims he was pulling in over $100,000 on single shows for Hank Jr.—an astronomical figure at the time. “I turned down Reba McEntire, turned down Garth Brooks, turned down Rascal Flatts to work for Hank Jr. for 24 years and was on call for 24 hours a day,” Pleasant says proudly.

But Eddie’s unconventional way of dealing with money, both in how he collected it and how he spent it, would eventually be his undoing from the Hank Jr. camp. When Hank Jr. married his fourth wife Mary Jane Thomas (and his current wife after a separation), many of the oldtimers from Hank Jr.’s camp were let go, including Eddie Pleasant. Eddie knew how to sell T-shirts better than anybody, but accounting and organization wasn’t his suit, and this put him sideways with Mary Jane.

“When Hank Jr. got married to Mary Jane Thomas, she wanted some control and they fired a lot of people,” says CJ Udeen. “They fired Merle Kilgore, Eddie, and others. After a few months, Merle Kilgore got his job back, but Eddie didn’t have that ability.”

After that, Eddie Pleasant began to fall on hard times. His songs weren’t selling anymore, and after spending four years out on the road with Hank Williams III, he spent some time working for a security business. But at 89-years-old, there’s not much left that Eddie can do. “I can’t run up and down the stairs carrying T-shirts anymore,” he says.

“He’s 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. He’ll turn 90 in June. He’s pretty frail. When I go over to visit him at the apartment, he might be lying in bed half napping. When he does get out of bed, he’s got an office in his apartment full of memorabilia with him and Hank Jr. and Willie. And to this day, he still trying to write songs and still getting out and going to the studio, trying to get another cut.”

“I keep hoping to get a big one,” says Eddie, who will cut out pictures from newspapers and magazines, and paste them onto his lyric sheets before sending them out. “Key to living is don’t smoke or drink they say. God I never did, but I’ve been around honky tonks all my life. My two ex wives are dead, so are my two daughters, and two grand kids. But we’ve got two grand kids we are raising. The girl is 9, and the boy is 13. Mamma’s 24 years younger than me, and I’ve had her for 38 years.”

Seeing the financial hardship Eddie Pleasant and his family have been suffering from, CJ Udeen recently set up a Go Fund Me account for Eddie. CJ’s current boss Gary Allan has taken up the cause, posting a link to the campaign on Facebook a number of times.

Eddie Pleasant's wife Lonna, and two grand kids.
Eddie Pleasant’s wife Lonna, and two grandchildren.

“There’s really no money there,” says CJ. “He’s living with his wife, and they had a daughter who OD’d and passed away about five years ago that had two kids, so they have two kids living with them in this apartment. His wife [Lonna Pleasant] is in her mid to late 60’s. She’s kind of the caretaker.”

According to CJ Udeen, Hank Jr. still looks fondly upon Eddie Pleasant. CJ remembers a time when both he and Pleasant were touring with Andy Griggs who opened for Hank Jr in 1999, and Eddie was reunited with Hank Jr. and his crew. “To see every one of those guys, including Hank Jr., come up to Eddie and hug on him, and the love every one of those guys had for him was just really special to see. Anybody that has ever come across him will just tell you that Eddie has the biggest heart of anybody they’ve ever met.”

At 89-years-old, Eddie Pleasant is still full of spunk, still trying to pitch songs, still sending out lyric sheets to studios, and driving down to Music Row occasionally to pester the secretaries at Curb Records or other labels to give his songs a shot.

“It’s awful to be 89-years-old with only a bunch of memories,” he says. “Save your money while your young.”

But the memories Eddie Pleasant has amassed for himself and country music fans along the way is something way more valuable than the crumpled cash you could fit in a fleet of Hefty bags.

– – – – – – – – –

Support Eddie Pleasant through Go Fund Me

– – – – – – – –

In the TV movie Living Proof based off the Hank Williams Jr. biography by Michael Bane, Eddie pleasant was played by Randy Patrick.


© 2024 Saving Country Music