30. Waylon Jennings & Willie Nelson, 'Waylon & Willie' (1978)
These old stoner compadres teamed up with startling purpose for this consistently poignant, pleasingly loopy Number One country smash. A last call of circular barroom logic, it evenly splits primo world-weary Willie (the quivering waltz "If You Can Touch Her at All" and bewildered end-of-the-line lament "It's Not Supposed to Be That Way") with top-tier wobbly Waylon (his chilling cinéma vérité version of Fleetwood Mac's "Gold Dust Woman" and the light-touch pathos of "The Wurlitzer Prize [I Don't Want to Get Over You"]). But the duets are the payoff: "Pick Up the Tempo" is outlaw country at its most lovable; Kris Kristofferson's "The Year 2003 Minus 25" lets the boys trade quasi-political WTFs; and on all-time jewel "Mammas Don't Let Your Babies Grow Up to Be Cowboys," they bare their road-ravaged souls with a high-plains-drifter conceit. It's since been covered by Karen O, Black Lips and Alvin and the Chipmunks. C.A.