The old souls rolling their eyes in 1993 at Garth Brooks flying around Texas Stadium on TV tipped their caps to Toby Keith’s celebration of the Wild West, "Should've Been a Cowboy," and for good reason.

Like Patsy Montana before him, the newest name on the country charts -- the song was Keith's debut single, from a stacked debut album -- wanted to ditch modern conveniences for the freedom once enjoyed by roping and riding cowpokes. The sentiment of "Should've Been a Cowboy" packs an even stronger punch 25-plus years later, as technology drives society further away from the simple, rural lifestyle still revered by many country music fans.

Despite the high praise for "Should've Been a Cowboy," it’s only one of 10 solid selections from one of the greatest debut albums of its time. The record contains three additional Top 5 singles, plus six album tracks that’ll leave even the most cynical listeners wondering why it took so long for such a talented vocalist and songwriter to go from working in the Oklahoma oil fields to living an ongoing Music City success story.

Below, The Boot ranks Toby Keith's tracks. No. 1 is probably obvious -- but maybe not the others.

  • 10

    “Ain’t No Thang”

    Unfortunately, something good has got to come in 10th when ranking one of the most stacked debut records in recent memory. Keith juggles inner heartbreak and outer confidence throughout "Ain't No Thang," one of the album’s more lyrically enriching selections. It reveals the soft side that’s needed to keep any pop culture cowboy grounded.

  • 9

    “Mama Come Quick”

    Like John Michael Montgomery and other contemporaries, Keith could slow things down in the ‘90s with a real tearjerker without losing his edge. In the case of "Mama Come Quick," he reminds those of us fortunate enough to have a strong female figure in our corner that she always knows just how to calm life’s storms with a few words of wisdom.

  • 8

    “Close But No Guitar”

    This whimsical acoustic performance sounds like a loose jam among friends when compared to the masterful production work on the rest of the album. It’s A-plus storytelling by a rising star who’d probably seen other guitarslingers catch all the breaks back in Oklahoma.

  • 7


    What sounds like a fun-yet-disposable pop-country nugget on first listen actually sums up the heartache, sadness and guilt that come along with a recent breakup. On "Valentine," Keith captures how certain inescapable holidays magnify those feelings, making this the perfect song to blare during that cathartic mid-February visit to the gym.

  • 6

    “Some Kinda Good Kinda Hold on Me”

    Beyond being a catchy song, this album cut set a lucrative trend in place for Keith: It’s his first song written or co-written by frequent collaborator Chuck Cannon. The buddies hit a grand slam a decade later with “American Soldier," but with this first outing, Cannon and co-writer Jimmy Alan Stewart made early ‘90s saxophone solos by someone other than Bill Clinton cool.

  • 5

    “Under the Fall”

    The best non-single on Keith’s debut album, "Under the Fall" could’ve made some noise on the charts 25 years ago. The instrumental intro reeks of the Highwaymen; after that ropes listeners in, they stick around for some of the tightest harmonies in a country song since the Statler Brothers’ heyday.

  • 4

    “Wish I Didn’t Know Now”

    Whether it’s a case of quality, familiarity or both, there’s no denying that the four singles off Keith’s self-titled debut deserve top billing on this list. Twenty years after the Faces sang “I wish that I knew what I know now,” Keith hummed a very different tune while coping with a cheating lover. Only Tim McGraw’s beloved “Don’t Take the Girl” kept this early-’94 hit from topping the charts.

  • 3

    “He Ain’t Worth Missing”

    Beneath its sentimental tone and syrupy production courtesy of the great Harold Shedd, "He Ain't Worth Missing" is a mid-tempo song that barely hides traces of its singer’s signature bravado. It finds basketball legend Wayman Tisdale’s buddy singing confidently about being more than just a one-night rebound for a heartbroken barfly.

  • 2

    “A Little Less Talk and a Lot More Action”

    In a year that began with Travis Tritt and Clint Black spreading the good word about rocking country music during the Super Bowl halftime show, Keith impressed with his own boot-scooting party anthem. His first impactful tale of a drunken night on the town and its carnal aftermath, "A Little Less Talk and a Lot More Action" offered fans a sneak peek at the flamboyance that added more bite to “How Do You Like Me Now?!,” “Red Solo Cup” and other future hits.

  • 1

    “Should’ve Been a Cowboy”

    Keith’s debut single celebrates cowboys’ freedom from everything except an honorable moral code; in the process, it reached the ears and touched the hearts of multiple generations of listeners, from Gunsmoke-watching parents to their line-dancing children. Despite tussling for airtime with record-breaking singles from Garth Brooks and Shania Twain, “Should’ve Been a Cowboy” went on to become country radio’s most-played hit of the decade.

More From 107.7 WGNA