[2] The song satirizes stereotypes associated with cowboys and gay men, with lyrics relating western wear to leather subculture: "What did you think all them saddles and boots was about?"

[1] The song was written during the Urban Cowboy fad[7] while living with his wife in Manhattan next to a gay country bar on Christopher Street called Boots and Saddles.

"[8] David Nahmod, however, stated that he felt the lyrics maintain currency and say "a lot about gender identity and heterosexual elitism";[9] "The song aims to show Mr. Nelson's support for gays, particularly to conservative country-music fans",[3] and suggests that, in addition to other causes, he supports gay rights.

[10] Nelson received a tape of the song from Saturday Night Live Band bassist Tony Garnier after performing on the show[11] in the mid to late 1980s.

According to Sublette, "Willie took it from there"[6] though Nelson recently found that demo in a drawer among a stack of his own while recording unreleased songs for iTunes at his Spicewood, Texas, home studio.

There were plans to release the song on a future album[13] and filming for the video featuring Broken Lizard Comedy Troupe[14] occurred at Dallas' gay cowboy bar, the Round Up Saloon (in Oak Lawn), in February 2006.

[16] Nelson himself described the release in a prepared statement to The Dallas Morning News:[12] "The song's been in the closet for 20 years.

[3] Nelson's version of the song is his highest charting solo single since his 1984 duet with Julio Iglesias, "To All the Girls I've Loved Before" (number 5),[1] debuting at number 52 on the Billboard Hot 100 chart, which Nelson last appeared on with the Toby Keith duet "Beer for My Horses".

Pitchfork Media's Stephen M. Deusner rated the song four out of four stars despite calling it "even more of a stunt than his reggae album" (2005's Countryman).

Similar to years ago, when the hippie thing come out and I started growin' my hair and puttin' the earring in, I got a little flak here and there.

[19] Nelson's broad audience, and part of the appeal of the song, may be that "Willie speaks his mind about any subject ... That's one of those things that has made him so endearing to so many generations of fans".

[19] When the song appeared as the penultimate track on Nelson's 2009 compilation Lost Highway, it was followed by a previously unreleased version of Willie singing Ben Hayslip's "Ain't Goin' Down on Brokeback Mountain", which includes the lyric "that shit ain't right."