“Should’ve Been a Cowboy” and “Who’s That Man” are an excellent two-song introduction to Toby Keith. The first imagines a freer life shaped by cowboy mythology; the second confronts the shock of returning to a life that now belongs to someone else. Released on Keith’s first two albums, both became No. 1 country hits and both were written by Keith himself.
Together, they show why his early catalog connected so quickly: clear storytelling, memorable titles, direct vocals, and narrators whose emotional situations are immediately understandable.
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Why these two Toby Keith songs belong together
Keith recorded many successful songs across his career, so these two should not be treated as a complete ranking or as his only important hits. They are, however, unusually effective bookends to his first breakthrough period.
“Should’ve Been a Cowboy” comes from Toby Keith, his self-titled debut album, dated April 20, 1993, on the artist’s official discography. It was his debut single and became his signature song. “Who’s That Man” followed on Boomtown, his second studio album, released in 1994.
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1Repair Windows errors before they cause bigger problems2Fix the driver behind crashes, sound loss and screen glitches3Clear out junk files and repair common Windows errorsBoth songs reached No. 1 on the U.S. Billboard Hot Country Songs chart, and both are identified in Keith’s official 100% Songwriter project as self-written songs. That combination matters: these were not just early songs that Keith happened to sing. They established him as a country storyteller with a recognizable point of view.
#1 Best Overall
| Song | Album | Central idea | Chart result |
|---|---|---|---|
| “Should’ve Been a Cowboy” | Toby Keith (1993) | Imagining freedom through the myth of the American cowboy | No. 1 on Hot Country Songs in 1993 |
| “Who’s That Man” | Boomtown (1994) | Returning to a former life and finding another man in your place | No. 1 on Hot Country Songs in 1994 |
“Should’ve Been a Cowboy”: the song that introduced Toby Keith
“Should’ve Been a Cowboy” gave Keith a character before it gave listeners a full biography. Its narrator looks toward an imagined Western life built from open space, independence, television Westerns, and the familiar idea of the cowboy as someone who answers to his own code.
That premise is important because the song is not a literal historical account of ranch work. It is a country-pop fantasy assembled from widely recognized Western images. The narrator is not presenting a detailed occupational portrait; he is imagining an alternative to ordinary life. The cowboy becomes a symbol of freedom, adventure, and self-definition.
The song’s broad fantasy is made personal through Keith’s direct first-person delivery. Rather than burying the premise in complicated imagery, the writing makes the narrator’s desire easy to understand: he believes another kind of life might have suited him better. That plainspoken approach became one of Keith’s defining strengths.
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The song’s durability comes partly from its accessibility. Listeners do not need to have worked on a ranch or lived in the American West to recognize the feeling behind it. Many people understand the wish that they had chosen a more adventurous, independent, or self-defining path.
Keith’s official biography describes the single as the record that propelled him to country prominence and later identifies it as his signature song. It reached No. 1 on the U.S. Hot Country Songs chart in 1993. The Songwriters Hall of Fame calls it a chart-topping song and credits it as the most-played country song of the 1990s, with more than three million radio performances. The Associated Press has also described it as Keith’s breakout hit and the most-played country song of that decade.
Rank #2
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That “most-played” description should be understood as an attributed radio-era distinction, not as a claim about current streaming totals. The song’s defining achievement was its impact on country radio and its role in establishing Keith at the beginning of the 1990s country boom.
The RIAA lists a certification for the single dated October 16, 2024, under Mercury Nashville. Certification records can be updated or presented in different catalog contexts, so the RIAA entry is the appropriate source to recheck for the current status at publication time.
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“Who’s That Man”: the darker side of being replaced
“Who’s That Man” changes the scale of the story. “Should’ve Been a Cowboy” looks outward toward a mythic life; “Who’s That Man” turns inward and asks what happens when a familiar life has continued without you.
The song’s narrator returns to a place associated with a former relationship and sees another man occupying the role he once held. The central question sounds like jealousy, but the deeper conflict is displacement. The narrator is not merely wondering who the replacement is. He is confronting the fact that his former identity—partner, resident, and familiar presence—has been taken over.
That makes the song more emotionally destabilizing than a conventional breakup complaint. The narrator is forced to look at evidence that the past is not waiting for him. The home, relationship, or community he remembers still exists, but it has been reorganized around someone else.
Rank #3
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Its place on Boomtown
“Who’s That Man” appears on Boomtown, Keith’s second studio album. The official Toby Keith discography dates the album to September 27, 1994, while Apple Music lists it as a Mercury Nashville release from September 17, 1994. The difference is best treated as a platform and catalog-date discrepancy rather than silently presenting one date as universally definitive.
Apple Music’s editorial description presents Boomtown as a loose concept album organized around a fictional boomtown. It places “Who’s That Man” among songs involving illicit or damaged relationships. That context broadens the song: it is not just an isolated story of romantic resentment, but part of an album world populated by people dealing with dissatisfaction, temptation, and consequences.
“Who’s That Man” reached No. 1 on the U.S. Hot Country Songs chart in 1994. The RIAA lists a certification for the single dated December 16, 2024, again under Mercury Nashville.
The contrast: imagined freedom versus unwanted change
The most useful way to hear these songs together is as two different directions of personal storytelling.
- “Should’ve Been a Cowboy” is expansive. Its narrator imagines riding away from an ordinary life and becoming part of a larger cultural myth.
- “Who’s That Man” is claustrophobic. Its narrator is pulled back into a familiar setting and discovers that he no longer belongs there.
- The first song projects a possible identity. The cowboy is the person the narrator wishes he might have become.
- The second song confronts a lost identity. The former partner and home reveal that the narrator’s old role has disappeared.
Despite that difference, both songs depend on the same core Keith technique: establish a situation quickly, give the narrator a clear emotional position, and build the song around a title that listeners can remember after one hearing.
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A free scan shows the junk files, broken settings and background clutter dragging Windows down - then fixes them in one click.Free scan · Windows 10 & 11They also show the range available within Keith’s early persona. He could move from a culturally familiar fantasy to a contemporary relationship drama without abandoning his direct, conversational style. The subject changes, but the storyteller remains recognizable.
The songwriting connection
Both songs are solo-written Toby Keith compositions. The official 100% Songwriter track list places them within his self-penned catalog, and the official store describes that compilation as a collection of Keith’s self-written hits.
This authorship helps explain why the songs feel like character statements rather than generic vehicles for a vocalist. “Should’ve Been a Cowboy” introduces a narrator who wants a different life. “Who’s That Man” introduces one who cannot recover the life he once had. In each case, the premise, title, and emotional conflict work together.
Keith’s writing here is not dependent on elaborate plot twists. The hooks come from situations that can be summarized in a sentence: a man wishes he had become a cowboy; a man sees another person living the life he lost. The simplicity is a strength because it makes the emotional stakes immediate.
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Where to start if you are exploring Toby Keith
Start with “Should’ve Been a Cowboy” if you want the most obvious introduction to Keith’s early public image: confident, accessible, Western-themed, and built around a large central idea. Follow it with “Who’s That Man” to hear the more vulnerable and unsettled side of the same songwriter.
Best Value
- Tim McGraw- Biggest Hits
For a physical release containing both songs, the official Toby Keith store lists Toby Keith 100% Songwriter vinyl. Check the current edition, seller, stock, and regional availability before buying, since an official-store listing and an Amazon listing may not represent the same offer.
If “Should’ve Been a Cowboy” is the song that interests you most, the self-titled Toby Keith debut is the natural next step. It places the single in the album that introduced him. If “Who’s That Man” makes the stronger impression, explore Boomtown to hear the broader fictional-boomtown setting and its damaged relationship stories.
After these two early landmarks, useful next stops include “A Little Less Talk and a Lot More Action,” “Dream Walkin’,” “You Shouldn’t Kiss Me Like This,” “How Do You Like Me Now?!,” and “I Love This Bar.” Those songs expand the picture beyond the cowboy fantasy and breakup narrative, while the central pairing remains the clearest introduction to Keith’s early songwriting identity.
Frequently Asked Questions
Were “Should’ve Been a Cowboy” and “Who’s That Man” both No. 1 country hits?
Yes. “Should’ve Been a Cowboy” reached No. 1 on the U.S. Billboard Hot Country Songs chart in 1993, and “Who’s That Man” reached No. 1 on the same chart in 1994.
Which Toby Keith album includes “Should’ve Been a Cowboy”?
It appears on Keith’s self-titled debut album, Toby Keith, dated April 20, 1993, in the artist’s official discography.
Which album includes “Who’s That Man”?
“Who’s That Man” appears on Boomtown, Keith’s second studio album. The official discography and Apple Music list different September 1994 dates, so the discrepancy is best treated as a catalog or platform-date difference.
Did Toby Keith write both songs?
Yes. Both songs are included in the official 100% Songwriter project, which presents Keith’s self-written hits.
The Bottom Line
“Should’ve Been a Cowboy” is Toby Keith imagining the life he might have chosen; “Who’s That Man” is Toby Keith facing the life that moved on without him. Their contrasting stories, shared directness, and No. 1 country success make them the strongest two-song gateway into his early catalog.
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