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.
This album comprised the first full-length work by Johnny Cash and Waylon Jennings as a duo, though they had previously worked together as part of the Highwaymen, the existence of whose three LPs may account for the relative neglect that Heroes has received. And it is one of the most obscure records in either artist's output, a fact that's astonishing, given the quality of the music, the singing, and the overall production. Co-produced by Chips Moman, and with Cash and Jennings at the top of their game (and so good at what they do that they make it sound easy), there's not a weak point anywhere here.
This double-disc reissue documents one of the more curious careers in country music. Both 1978's White Mansions and 1980's The Legend of Jesse James are Southern song cycles that were conceived by Britain's Paul Kennerley, then an unknown songwriter who somehow recruited a high-profile cast for each. A Civil War saga from the Southern perspective, White Mansions suffers from caricature and cliché but benefits from signature contributions by Waylon Jennings, Jessi Colter, and Eric Clapton. Jesse James has more focus and narrative momentum, with Levon Helm, Johnny Cash, and Emmylou Harris in lead roles. Though the albums are more noteworthy for artistic ambition than memorable material, Kennerley subsequently became a successful Nashville songwriter.