Songs Similar to Should've Been a Cowboy by Toby Keith
Album: Toby Keith 35 Biggest Hits · Country · Happy
Toby Keith's “Should've Been a Cowboy” from the album Toby Keith 35 Biggest Hits is a country track that we file under happy songs. If it's the one you keep replaying, the list below collects tracks that fans of it also play; the original moves at roughly 136 BPM.
The closest match right now is “How Do You Like Me Now?!” by Toby Keith (100% match). The list also pulls in Brooks & Dunn, Billy Currington, Travis Tritt and Dierks Bentley — artists whose audiences overlap heavily with Toby Keith's. By genre, the list is mostly country (18 of 20 tracks), with pop mixed in. Each entry shows its genre and a match score, so you can start with the strongest matches and work outward. Every song links out to YouTube, Spotify and Amazon Music for a quick listen, and the ones marked as links have their own similar-song pages here.
20 songs similar to “Should've Been a Cowboy”
- 1
- 2
- 3
- 4
- 5
- 6
- 7
- 8
- 9
- 10
- 11
- 12
- 13
- 14
- 15
- 16
- 17
- 18
- 19
- 20
Data: Last.fm, updated 2026-10-11.
More songs by Toby Keith
We don't have other Toby Keith songs yet — here are country songs from the same era:
More Country songs
- Songs similar to Fast Car · Luke Combs
- Songs similar to Beautiful Crazy · Luke Combs
- Songs similar to A Bar Song (Tipsy) · Shaboozey
- Songs similar to 9 to 5 · Dolly Parton
- Songs similar to Friends in Low Places · Garth Brooks
More Happy songs
- Songs similar to Dog Days Are Over · Florence + The Machine
- Songs similar to Pumped Up Kicks · Foster The People
- Songs similar to Riptide · Vance Joy
Find more songs similar to any track
Enter any song in the similar song finder, or browse all genres.
FAQ about “Should've Been a Cowboy”
What songs are similar to Should've Been a Cowboy?
On our list, the closest matches are “How Do You Like Me Now?!” by Toby Keith, “As Good as I Once Was” by Toby Keith and “Write This Down” by George Strait. All 20 songs on this page are ranked by how strongly their listeners overlap with fans of “Should've Been a Cowboy” by Toby Keith, so the higher a song sits, the closer it is to the original's sound and audience.
Who does Should've Been a Cowboy sound like?
Based on listening data, “Should've Been a Cowboy” sits closest to George Strait, Brooks & Dunn, Billy Currington and Travis Tritt. Fans of Toby Keith play these artists more than almost anyone else, which usually means a shared sound, era or scene. Start with their tracks in the list above if you want something in the same vein.
Is Should've Been a Cowboy Country?
We file “Should've Been a Cowboy” by Toby Keith under Country. Genre labels are fuzzy, so the similar songs above aren't limited to one genre — they follow what listeners actually pair with the song.
How do you find similar songs to Should've Been a Cowboy?
Use the list on this page: it ranks 20 tracks by how often fans of “Should've Been a Cowboy” also listen to them. Open any song that has its own page to keep exploring, or enter another track in the similar song finder to start a new list.