Willie Nelson vs. Orville Peck | Head 2 Head

In the 20^th edition of Head 2 Head (2024), Willie Nelson and Orville Peck contend for the best rendition of “Cowboys Are Frequently Secretly Fond of Each Other.”  

Welcome to Head 2 Head! On Head 2 Head, we pit at least two musicians performing the same song, comparing their respective performances.  Then, after much deliberation, we deliver a verdict of which performance was the best, or at least, subjectively, which performance moved us more.  In the 20^th edition of Head 2 Head (2024), Willie Nelson and Orville Peck contend for the best rendition of “Cowboys Are Frequently Secretly Fond of Each Other”. So, without further ado, let the Head 2 Head commence!

1. Willie Nelson, “Cowboys Are Frequently Secretly Fond of Each Other”

Lost Highway // UMG Recordings, Inc. // 2009 

“Well, a cowboy may brag about things that he’s done with this women / But the ones who brag loudest are the ones that are most likely queer.” Woo! How often does it seem that men who aren’t comfortable with their masculinity and sexuality feel they need to brag about (and likely, exaggerate) their conquests? That’s explored in “Cowboys Are Frequently Secretly Fond of Each Other”.  Cowboys have ‘gay’ sensibilities, and tendencies, and historically, some participated in same-sex activities. Back in 1981, Ned Sublette wrote and recorded a rare gay country song. “Cowboys Are Frequently Secretly Fond of Each Other” has become known as the gay cowboy song. In 2006, one of country music’s legends, Willie Nelson, recorded a high-profile cover. 

The Nelson version, which ultimately appears on his 2009 album, Lost Highway, arrived at a more ‘accepting’ time for LGBTQ-themed music. “Cowboys” has some old-school lyrics, but still relevantly highlights sexuality, gender, and stereotypes, making it a unique conversation piece. It’s humorous, but also, it’s clear Sublette was making a statement.

“Cowboys are frequently secretly fond of each other 

Say, what do you think all them saddles and boots was about? 

And there’s many a cowboy who don’t understand the way that he feels for his brother 

And inside every cowboy, there’s a lady that’d love to slip out.”  

For good measure, there’s even a f-bomb, which easily comes off of Willie’s tongue: “So, when you talk to a cowboy don’t treat him like he was a sister / You can’t fuck with a lady that’s sleepin’ in each cowboy’s head.” “Cowboys Are Frequently Secretly Fond of Each Other”, a post-Brokeback Mountain gem, may be funny and silly to an extent, but it’s also a great conversation piece.  Interestingly, nearly 20 years later, Nelson re-covered “Cowboys”…

Appears in 🔻:  

• Willie Nelson, Cowboys Are Frequently Secretly Fond of Each Other: LGBTQ Bopz 🌈🎶 3 (2022)
• Incredible LGBTQ Songs, Young & Old, Vol. 2 (2022)

2. Orville Peck & Willie Nelson, “Cowboys Are Frequently Secretly Fond of Each Other”

“Cowboys Are Frequently Secretly Fond of Each Other” // Orville Peck, LLC / Warner // 2024

Remember how I mentioned that Willie Nelson re-covered the gay cowboy country song, “Cowboys Are Frequently Secretly Fond of Each Other”? Well, in 2024, beloved, fringe-masked, gay country artist, Orville Peck, duets with Nelson in this queer country gem.  This 2024 rendition of “Cowboys Are Frequently Secretly Fond of Each Other” was produced by Beau Bedford.

The instrumental is subtle, which is perfect for allowing Peck and Nelson’s voices to shine. Peck starts things off, with his expressive, masculine baritone.  His tone is EVERYTHING. Gay men are often pigeonholed and stereotyped as being effeminate. Just hearing a ‘manly’ voice, from an openly gay musician, singing lyrics about male/male relationships is intriguing (“No, a small town don’t like it when a cowboy has feelings for men”). Following Peck’s verse, Nelson performs the second, delivering one of the best lyrics of the song: “But the ones [cowboys] who brag loudest are the ones that are most likely queer.” Peck and Nelson join forces in the choruses, bringing out the cowboy love. Following an instrumental break, Peck takes over the reins in the third verse, once more wowing with his awesome pipes.  He gets the honor of dropping the f-bomb (“You can’t fuck with a lady that’s sleepin’ in each cowboy’s head”). Peck and Nelson joining forces on “Cowboys Are Frequently Secretly Fond of Each Other” is nothing short of magic!

Appears in 🔻:

• Bops That Pop: April 2024

The Verdict 👨🏿‍⚖️ 

So, who covered the Ned Sublette, gay cowboy country song the best? Was it the 2006 rendition by Willie Nelson, or the 2024 duet by Orville Peck and Nelson? Either way, Nelson doesn’t lose! Both covers are incredible – soundly executed.  I love the fact that a younger artist and an icon collaborate on a progressive song in a conservative music genre. I also love the fact that the icon, Nelson, covered this uncharacteristic song nearly 20 years before the duet version, in a more conservative time.  Also, did you know that Peck covered Nelson’s cover on the 2023 album, Long Story Short: Willie Nelson 90 (Live at the Hollywood Bowl)? That’s a lot of covering.  With that said, give the edge to the 2006 take by Willie Nelson – it’s epic!

Willie Nelson vs. Orville Peck: Head 2 Head No. 20 (2024) [📷: Brent Faulkner / The Musical Hype; [📷: Brent Faulkner / The Musical Hype; Orville Peck, LLC, UMG Recordings, Inc., Warner; Hernán Toro, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]