Dwight Yoakam, Willie Nelson

There is perhaps no man in the music business as smart as Dwight Yoakam -- not necessarily biz smart (not a wise move wearing out "Crazy Little Thing Called Love" in a Gap ad before it surfaced on the recent best-of), not even book smart (never gave him a pop quiz). By smart, I mean only thoughtful, literate, precise, learned, passionate. By smart, I mean Dwight Yoakam is a man given to long, thoughtful interviews during which you're as likely to discover his penchant for painter Arshile Gorky as you are his affinity for, say, Buck Owens; and somehow, he will bring both men into a conversation, insisting one relates to the other. I've spent hours with the man -- on the phone, in hotel suites -- and have always come away wondering whether he's the most sagacious man ever to don a cowboy hat and second-skin leather pants. He can turn an hourlong interview into an afternoon-long discourse on the pleasures of "Wichita Lineman," William De Koonig, Frank Sinatra, and collaborator Billy Bob Thornton. A naive person might say Yoakam's too smart for country music, at least as it exists now in its dumbed-down, shined-up form. The knowing fan will insist it's the perfect avenue for Yoakam; peg him as nothing more than a traditionalist/revisionist, and you've underestimated his genius.

Then again, he is a man who long ago planned his career -- he fashioned himself as the modern-day Gram Parsons, dolled up in Nudie suits and nail-sharp boots -- and followed through, until the gates of Sin City opened up to reveal treasure chests full of gold and platinum. He might well have stayed home in Kentucky and died in the mines, like so many of his relatives, or pumped gas like his daddy. But the boy had ambition when he moved to Los Angeles in 1976, looking for his own room in the gilded palace of sin. It would be another decade before he got his own record in stores, but by then, it was as clear as the L.A. sky after a fall rainstorm that Yoakam was more than just another Flying Burrito step-son. The dude was the real thing in Plastic City, an outsider who found a way in through punk-rock's doorway, sharing bills with X and Los Lobos, musicians also reshaping "traditional" American idioms. He would go on to make some of country music's most essential modern-day records -- among them 1988's Buenos Noches From a Lonely Room, 1990's If There Was a Way, 1993's This Time -- but outgrow the genre just about the time he became a natural at it. Like Buck Owens once said: Dwight ain't country, only because he "transcends the genre."

Listen only to 1995's Gone to realize the breadth of his talent -- the Buddy Holly dip, the Tijuana Brass soul, the Beatles pop-pop, the Roy Orbison ooby-dooby. Or 1997's Under the Covers, with its Rolling Stones and Jimmy Webb and Sonny and Cher redos fashioned with a hint of irony. Or the same year's Come on Christmas, with its jingling bells and ringing brass. The man who used to sing about his old Kentucky home suddenly owned the world and sang like he knew it; imagine Frank Sinatra in ripped jeans...and without the hairpiece. Maybe that's why last year's A Long Way Home sounded like such a disappointment: It played like a step backward, toward safe and familiar ground, rather than the next obvious leap into the great unknown. Too bad, then, that his great unknown turned out to be a Queen cover for Last Chance for a Thousand Years: Dwight Yoakam's Greatest Hits from the '90s. It's mediocre for one simple reason: It doesn't ring true. Though it may ring a Gap cash register or two.

It's only appropriate he share a bill with Willie Nelson; they're fellow travelers along the same road of detours and dips. The only difference is that Yoakam's got a weak spot for rock, and Willie's still nursing his Tin Pan Alley fetish. Indeed, Nelson's brand-new record, Night and Day (released on his own Pedernales label), is loaded with Jules Styne ("Vous et Moi"), Cole Porter ("Night and Day"), Hammerstein-Kern ("All the Things You Are"), and Fats Waller ("Honeysuckle Rose") gems -- all performed as instrumentals. It was inevitable, perhaps, that Nelson make such a record: He's Django Reinhardt and Hank Williams rolled into one dope-smoking sumbitch who gets better the more he ages and the more he tokes. The dude ought to be everyone's hero.