Born in Kentucky on This Day in 1944, the King of Honky Tonk and the Most “Outlaw” Country Singer of the 1970s

On this day (May 28) in 1944, Gary Stewart was born in Dunham, Kentucky. His career, which spanned three decades, wasn’t marked by accolades, awards, and a long string of hit singles, nor did he pack arenas or stadiums. Instead, he released a handful of hits in the mid-1970s, toured honky tonks and Native American reservations for most of his life, and made music that was a little too country for the rock crowd and a little too rock for country purists. However, his wild antics, vibrato vocals, and songwriting prowess allowed him to leave an indelible mark on the face of country music. Today, modern artists and audiences are giving him the admiration that he deserved while he was alive.

Videos by American Songwriter

Stewart began his rise to the honky tonk throne as a teenager. He learned to play guitar and piano and began writing songs. He married at 16 and took a factory job at 17. At night, he played with various rock and country bands around Florida. One evening, he met country singer Mel Tillis, who told him he should go to Nashville and pitch his songs on Music Row. In 1964, when he was 20 years old, he took Tillis’ advice.

[RELATED: 3 Country Music Songs of 1975 That Sound Even Better Today]

Answering Nashville’s Call

According to the Kentucky Music Hall of Fame, Stewart started making regular trips to Music City and writing songs with Bill Eldridge. Together, they penned hits for Billy Walker, Jack Greene, Del Reeves, and Cal Smith. While he was seeing some success as a songwriter, his recording career, which consisted of a few unsuccessful singles for Kapp Records, wasn’t taking off. Then, he heard the Allman Brothers Band for the first time.

His lack of success and the influence of the Allman Brothers led him to return to Florida and begin honing his signature honky tonk sound. Stewart’s bread and butter came from a combination of rock, country, blues, and bluegrass. That blend, combined with his instantly recognizable vocal style, helped him rise to the top of the country world for a short time.

Gary Stewart Finds Chart Success

In the early 1970s, Gary Stewart recorded a handful of demo tapes. The recordings included retooled Motown hits and original songs. Eventually, those tapes found their way to Roy Dea, who helped Stewart land a deal with RCA Records. By this time, he had forged a friendship with Gregg Allman and his recently deceased brother Duane. So, his debut single on RCA was, fittingly, a cover of “Ramblin’ Man,” which failed to break the top 40 upon its release in 1973.

The next year, Stewart released “Drinkin’ Thing,” which peaked at No. 10. He followed that with “Out of Hand,” the title cut from his debut RCA album. It was a top 5 hit. In 1975, he scored his sole No. 1 with “She’s Actin’ Single (I’m Drinkin’ Doubles).”

Stewart released several minor hits throughout the remainder of the decade. However, he never reached the top 10 again. The songs’ chart positions didn’t indicate their quality, though. “Ten Years of This,” “Quits,” “In Some Room Above the Street,” and “Flat Natural Born Good-Timin’ Man” are all country gold, despite where they landed on the Hot Country Songs chart.

Stewart didn’t shape his legacy with chart success. Instead, the quality of his music and the intensity of his live shows spoke for themselves. To quote biographer Jimmy McDonough, “His was a music of dangerous, wild abandon.”

Stewart Never Wanted to Be a Star

Unlike many artists in his position, Gary Stewart didn’t care about fame or fortune. “Stardom was no goal, nothin’ I ever chased,” he once said. Over the years, people tried to get him to launch a nationwide tour or to travel to New York or Los Angeles to play. However, he had no interest in doing so.

“Gary preferred to stay home, lie on the couch, and watch Charles Bronson as Wild Bill Hickock on the hunt for The White Buffalo,” Jimmy McDonough, who spent a considerable amount of time with the singer, wrote. “Mention a no-name club in some Texas twilight zone, though, and Gary’s eyes grew big.”

Gary Stewart Left His Mark

While he didn’t care about being the biggest star in country music or rock and roll, Gary Stewart still left his mark on the music world. Willie Nelson, Dean Dillon, Dwight Yoakam, Vince Gill, members of the Clash, and Bob Dylan were all fans.

Before his recording career took off, Stewart was a member of Pride’s road band. Notably, he played piano on the Pride’s live album In Person. Dylan called “Ten Years of This” one of his favorite songs.

Stewart and Dillon cut two duet albums together in the early 1980s. While they weren’t successful, the pair of songwriters created songs that have stood the test of time. For instance, they co-wrote “Leave Them Boys Alone” with Tucker, which became a hit for Hank Williams Jr. He and Dillon also co-wrote “An Empty Glass,” which continues to be a staple in the Texas country scene. “Every band in Texas plays that song,” Dillon said. “To this day, when you close a show in Texas, it’s ‘An Empty Glass.’”

Tucker called Stewart “A honky tonk man with a honky tonk heart.” She added, “Man, ain’t nobody could ever sing honky tonk music like Gary Stewart. One of the greatest country singers of all time… There was nobody better.”

His work has also become popular with some Texas-based contemporary musicians. For instance, Cody Johnson recorded “She’s Actin’ Single (I’m Drinkin’ Doubles)” in 2022. Two years earlier, Silverada, who were still Mike and the Moonpies at the time, released Touch of You: The Lost Songs of Gary Stewart.

Stewart died by suicide at the age of 59 in December 2003, less than a month after his wife of more than 40 years passed away. His legacy, though, lives on.

Featured Image by Michael Ochs Archives/Getty Images