Watch: Robert Earl Keen’s Cover of Oliver Tree’s ‘Cowboys Don’t Cry’ Is a Tearjerker

by Jim Casey

A couple of days before Texas troubadour Robert Earl Keen, 66, announced his retirement tour on January 14, 2022, enigmatic entertainer Oliver Tree released his new music video for “Cowboys Don’t Cry” on January 12, the lead single from his second studio album, Cowboy Tears. The video currently has more than 27 million views (which dwarfs in comparison to some of Tree’s other videos). In fact, 29-year-old Tree came out of “retirement” to release Cowboy Tears on Feb. 18. One cowboy was retiring, one was coming out of retirement.

And now, the paths of the two cowboys have crossed, sonically speaking. Robert Earl recorded a cover of Tree’s “Cowboys Don’t Cry” on The Next Waltz, the Bruce Robison-produced series/label that allows artist to release digital singles/videos recorded in his studio in Lockhart, Texas.

Cowboy Cover

As unlikely as the intersection seems, it’s not. While REK is known—or should be—for his songwriting prowess and ability to turn an entertaining lyric across his more than a dozen studio albums, he knows the opportunity for a great cover when he hears it (see REK’s covers of Townes Van Zandt’s “Snowin’ on Raton,” James McMurtry’s “Out Here in the Middle,” or Todd Snider’s “Play a Train Song”).

While Tree’s video, which starred actress Bella Thorne, provides plenty of levity (see the motorized bull-mobile), REK’s clip is a straight tearjerker.

At least, it is when you couple the lyrics with Keen’s retirement from touring. Keen, eyes shut, delivers the song’s opening lines with his distinct croon: “I’m not good at goodbyes / I miss the sunshine in your eyes / Who said cowboys don’t cry? / Come on, baby, let’s take one last ride.”

REK’s Farewell Tour

In fact, REK is saying goodbye—at least from touring—right now. He’s in the midst of his farewell I’m Comin’ Home Tour. After more than 40 years on the road, Keen will hang up his touring boots with one final show on Sept. 4 at Floore’s Country Store in Helotes, Texas.

I’ll be there, man. You should, too. Or, at least at one of his remaining 30-plus dates.

While Robert Earl Keen is retiring from the road, he noted in his video message on January 14 that he will continue to record and release new music. And for that, we are thankful.

REK’s cover of the Tree-penned “Cowboys Don’t Cry” is a welcome addition to his cowboy catalog—if you catch my drift.