
When Toby Keith played nighttime bar sets with his band Easy Money in the early 1980s, a pager clipped to his belt could pull him off the stage in the middle of a song to report back to the Oklahoma oil fields. Long before he sold 40 million albums, the singer born Toby Keith Covel spent his late teens and twenties splitting his hours between 24-hour drilling schedules around Elk City and smoky dance halls across the Red River region.
Born in Clinton, Oklahoma, on July 8, 1961, Keith learned the pace of physical labor from his father, Hubert K. Covel Jr., an Army veteran who had lost an eye in a military accident and worked in the oil business to keep his family afloat. While spending summers in Fort Smith, Arkansas, at Billy Garner’s Supper Club, a tavern owned by his grandmother, Keith washed dishes and sat in with the house band after receiving his first guitar at age eight.
After returning to Moore, Oklahoma, where he played defensive end for the Moore High School football team, Keith initially considered studying petroleum engineering in college. When crude prices surged in the spring of 1979, the 18-year-old skipped campus and followed his father directly into the booming oil patch around western and central Oklahoma.
Starting at the bottom as a roustabout and derrick hand, Keith hauled steel pipe in triple-digit summer heat and worked high on the rigs through freezing plains winds. He later told interviewer Dan Rather that oil-patch money came fast during the boom, allowing him to work his way up from roughneck crews to operations manager by age 20.
Many of the men assigned to his crews were twice his age, so Keith avoided giving orders from behind a desk. He climbed down into the mud to work heavy shifts alongside them and ate lunch beside the pipelines, listening as older hands talked through their bills, marriages, and families.
Outside the oil patch, Keith and his friends Scott Webb, Keith Cory, David “Yogi” Vowell, and Danny Smith formed the Easy Money Band in 1980. At night, Keith scrubbed the grease from his hands, sang four-hour sets of country covers and early originals in local roadhouses, and drove straight back to the rigs at dawn if his pager buzzed.
That double life collapsed in 1982 when the Penn Square Bank failure and the wider Oklahoma oil bust wiped out drilling companies across the state. While co-workers sold off their pickups and homes to survive, Keith lost his oil-field job, laid brick to pay the rent, and spent two seasons playing defensive end for the semi-pro Oklahoma City Drillers alongside teammates waiting for the USFL’s Oklahoma Outlaws.
By 1984, the year he married Tricia Lucus, Keith walked away from football to put everything on Easy Money. For the rest of the decade, the band loaded gear into a van and toured a grueling circuit of honky-tonks and dance halls stretching from Arkansas and Texas to Colorado and Arizona.
During a hunting trip to Dodge City, Kansas, with Webb and other bandmates, Keith watched a man in a cowboy hat steer a young woman across a dance floor at a club called The Cowboy while another friend remarked, “You should’ve been a cowboy”. Keith wrote the song in a motel bathroom that night, testing it for years in front of rowdy bar crowds before taking his demo tapes to Nashville.
When Music Row labels rejected him and a brief single on independent Hometown Records stalled in 1990, Keith busked on Nashville sidewalks and vowed to walk away if he did not have a major contract by age 30. That break arrived when flight attendant Dorieenga “Dorie”reme passed his cassette to Mercury Records executive Harold Shedd on an airplane, prompting Shedd to fly out, watch Keith command a club room, and sign him.
Released in February 1993 when Keith was 31, “Should’ve Been a Cowboy” went to No. 1 and became the most-played country song of the 1990s. Even as 20 Billboard No. 1 hits followed, Keith stayed in Oklahoma, founded the Toby Keith Foundation to open the OK Kids Korral for pediatric cancer families in Oklahoma City, and died in his home state on February 5, 2024, at age 62, hours after his election to the Country Music Hall of Fame.
Years after the derricks around Elk City went quiet, the calluses from hauling drill pipe stayed on his hands, and the roughnecks who once shared lunch beside the pipelines remained the voice inside the songs he carried from Oklahoma barrooms to stadiums across America.