“My Favorite Song I Ever Recorded” — Waylon Jennings’ “Dreaming My Dreams With You” Is A Stone Cold Country Heartbreaker

Waylon Jenning country music
Waylon Jennings/Youtube

Talk about a stone cold country heartbreaker.

The one and only Waylon Jennings is one of my favorite artists of all-time, and it would be nearly impossible for me to settle on just one favorite from his expansive catalog of incredible music.

Depending on the day, I find myself gravitating towards a different Waylon tune, which in my opinion, is the mark of a truly great artist. There’s something for every mood and everybody. But one that will forever have a spot in my top-five list is his single “Dreaming My Dreams with You.”

Written by Allen Reynolds, Waylon recorded it for his 1975 Dreaming My Dreams album. The song peaked at #10 on the U.S. Billboard Hot Country Songs chart.

And because it’s a country classic, it’s been covered by tons of other artists since Waylon, like Emmylou Harris and Rodney Crowell, Cowboy Jack Clement, Cowboy Junkies, Alison Krauss, Crystal Gayle, Patty Loveless, Martina McBride, Mark Chesnutt, John Prine, just to name a few.

But one of the best covers comes from the great Jamey Johnson, who included his version on his 2008 second studio album That Lonesome Song, which featured another Waylon cover in “The Door Is Always Open.”

Koe Wetzel once went so far as to say that it’s the best country song ever written:

“Dreaming my dreams with you by Jamey Johnson is the best country song ever written.”

And honestly, as much as I love Jamey’s version and think it’s a great cover, I’d have to beg to differ and say Waylon’s original version is up there on the list of the greatest country songs ever. But lyrically, I’d have to agree that it’s certainly one of the best by a long shot.

There’s just something about the woozy steel guitar and agonizing, forlorn lyrics that paint such a sad picture of a man who’s trying to get over a heartbreak, but can’t quite seem to move on, no matter what he tries.

He says what he’ll miss the most about the woman he loved so dearly is “dreaming my dreams with you,” which gets me every single time. Is there a more poignant and regretful way to say you’re heartbroken than that line? Geez…

Plus, hearing Waylon deliver it with that trademark voice and the weightiness of the signature, commanding gravitas in his vocals is just top-tier, and I can’t say enough good things about it. These are the songs that made him an icon and a legend.

In a 1984 performance for his Live from Austin, TX album, he said:

“I guess this is my favorite song I ever recorded.”

That’s quite a statement from one of the greatest country artists to ever do it, but it’s easily one of mine, too. If you don’t know this tune and like a classic country heartbreaker, you’ll absolutely love this one:

And make sue you check out Jamey’s cover while you’re here, as well:

“Dreaming My Dreams with You”


A beer bottle on a dock



A beer bottle on a dock