Dreaming My Dreams was Waylon Jennings' first number one record, and deservedly so. He had created outlaw country with Honky Tonk Heroes, and then delivered two further albums that subtly developed its themes, even if they weren't quite as consistent. Dreaming My Dreams maintains the consistency, increasing the country quotient while subtly making it more sentimental than before. This is an unabashedly romantic album, not just in its love songs, but in its tributes to Waylon's heroes. "Are You Sure Hank Done It This Way" opens and "Bob Wills Is Still the King" closes the album -- making Jennings an heir apparent to their legacies. Between those two extremes, Waylon appropriates Jimmie Rodgers ("Waymore's Blues"), covers Roger Miller ("I've Been a Long Time Leaving [But I'll Be a Long Time Gone]"), ups the outlaw ante ("Let's All Help the Cowboys [Sing the Blues]"), and writes and records as many sentimental tunes as possible without seeming like a sissy. At times, the emotional undertow may seem a bit much, yet the whole thing adds up as Waylon's best album since Honky Tonk Heroes, and one of the few of his prime outlaw period to deliver from beginning to end.
AllMusic Review by Stephen Thomas Erlewine