Big & Rich, "Save A Horse (Ride A Cowboy)"
By "ride a cowboy," they mean sexual intercourse, ladies. Wink Wink. You get it? Cowboys want you to have sex with them, LOL.
*NSYNC, Space Cowboy (Yippie-Yi-Yay)"
This song makes all the sense in the world in hindsight. You see, cowboys are frequently used as gay stereotypes.
Sting, "This Cowboy Song"
Fuck Sting.
Counting Crows, "Cowboys"
Remember all the prime tail that Adam Duritz, a Jewish man with fake dreadlocks, used to pull in the '90s? Didn't he sleep with all the Friends girls, even Gunter? According to Duritz's Wikipedia entry, he lived in Houston for a span of time. Did anybody know him then?
Toby Keith, "Should've Been A Cowboy"
Believe it or not, Toby Keith has a greatest-hits set called Toby Keith: 35 Biggest Hits. Can you imagine that? We can maybe think of five or six we would download (steal), but 35 is a stretch.
Fenix TX, "Apple Pie Cowboy Toothpaste"
Fenix TX used to be called River Fenix and used to play Fitzgerald's all the time, true story.