Jennings deservedly developed a reputation as one of country’s true outlaws, turning his back on Nashville conventions that left him feeling straitjacketed in the 1960s. So he (along with Willie Nelson) kissed Music City goodbye and headed back to their native Texas to make music their way, a move that brought much-needed new energy and bold artistic vision to country in the '70s.
While Jennings scored some of his biggest hits with uptempo songs that oozed testosterone, such as “Are You Sure Hank Done It This Way,” “I’ve Always Been Crazy” and “I’m a Ramblin’ Man," many of his greatest performances were the ballads, which he delivered with uncommon sensitivity.
A prime example is “Dreaming My Dreams With You,” a song he once described as “my favorite song I ever recorded”; his recording delivers 2 minutes and 26 seconds of country perfection.
It reached only No. 10 on the Billboard country singles chart when it was released in 1975, but it has become legendary in country circles, and subsequently recorded by dozens of artists, including Alison Krauss, Jamey Johnson, Cowboy Junkies, Jewel, Crystal Gayle, Collin Raye, Mark Chesnutt and, most recently, Emmylou Harris and Rodney Crowell on their forthcoming duo album, “Old Yellow Moon.”