Waylon Jennings gave country music some of its rowdiest anthems. But when he was asked which of his own recordings meant the most to him, he didn’t pick an outlaw hit. He picked “Dreaming My Dreams with You,” a quiet 1975 ballad that only climbed to No. 10 on the Billboard country chart. Standing on stage in Austin in 1984, he put it simply:
“I guess this is my favorite song I ever recorded.”
Coming from Waylon, that says a lot. Here is how the song found him, and why it stayed with him long after the bigger hits had faded off the radio.
It Started at a Friend’s Thursday Night Session
Waylon didn’t write “Dreaming My Dreams with You.” It came from Allen Reynolds, a songwriter friend of the legendary producer “Cowboy” Jack Clement.
Clement had been Sam Phillips’ right-hand man at Sun Records, where he worked with Johnny Cash and Jerry Lee Lewis. In Nashville he held Thursday night demo sessions at his own studio, and he invited Waylon to come by. That night Allen Reynolds sang “Dreaming My Dreams with You.”
Hearing it did more than make Waylon want to cut one song. It inspired him to make a whole album, and he asked Clement to produce it with him. Waylon later called Jack Clement a “sheer-out genius, all soul.”
Recorded the Hard Way
By then Waylon had finally won the fight he’d been waging with Nashville for years. In 1972 his manager renegotiated his RCA contract and got him full artistic control. He no longer had to record with the label’s studio players or on the label’s terms.
The new album was recorded between February and July 1974 at Glaser Sound Studios in Nashville. Clement liked to capture songs live, with as few overdubs as possible. That approach suited a ballad like this one. What you hear on the record is mostly a band in a room with a singer who meant every word.
The sessions themselves were anything but peaceful. There was miscommunication, there was Waylon’s drug use, and at one point an argument got so heated that Waylon walked out and stayed away for about two weeks. He came back only after a dinner with Clement and his wife. Out of all that turmoil came one of the gentlest songs of his career.
A Quiet Song on a Loud Album
The album, also titled Dreaming My Dreams, came out in June 1975. Its opening track, “Are You Sure Hank Done It This Way,” hit No. 1 and became an anthem of the outlaw movement. It pounds and buzzes, and it seems to challenge Nashville to argue with it.
“Dreaming My Dreams with You” sits near the end of side two, and it couldn’t be more different. There’s no challenge in it at all. It’s a man facing the end of a love he can’t hold on to, and he isn’t angry about it. He simply admits that he will go on dreaming about her anyway. Waylon sings it low and plain, with none of the swagger people expected from him.
Released as a single with “Waymore’s Blues” on the B-side, it peaked at No. 10. That was respectable, but it wasn’t the kind of record that made Waylon a superstar.
Why It Mattered So Much to Him
The album did make him a superstar. Dreaming My Dreams went to No. 1 on the country albums chart and became his first gold record. That same year Waylon was named the CMA’s Male Vocalist of the Year. Decades later, Rolling Stone ranked the album No. 2 on its list of the 100 Greatest Country Albums of All Time.
Waylon never forgot where it began. In his 1996 autobiography he named Dreaming My Dreams as his favorite of all his albums. On stage in Austin he went a step further and named its quietest song as his favorite recording.
For a man the world knew as an outlaw, that choice reveals something. Underneath the black hat and the hard-living stories was a singer who knew that the bravest thing he could do was sound vulnerable, and he was proudest of the night he let it show.
The Song Outlived Its Chart Number
No. 10 turned out to be only the beginning. Over the years “Dreaming My Dreams with You” has been recorded by Emmylou Harris and Rodney Crowell, Alison Krauss, Patty Loveless, Crystal Gayle, Martina McBride, Jamey Johnson, Collin Raye, Cowboy Junkies, and John Prine with Kathy Mattea. Marianne Faithfull’s 1975 version went to No. 1 in Ireland.
Many of those singers heard the same thing Waylon heard at Jack Clement’s session that night: a song that doesn’t shout, and doesn’t need to.
Do you remember the first time you heard Waylon sing this one? Was it on the radio, on the album, or years later when someone played it for you?