Bob Dylan's fascination with Cadillac (NYSE: GM) can be traced back to his first album, Freewheelin' Bob Dylan. In "Talkin' World War III Blues," Dylan imagines driving a Cadillac through Manhattan, declaring it's a "good car to drive, after a war."

Now, the singer has signed on to star in a multi-platform marketing campaign for the storied brand. The campaign will be tied into the Theme Time Radio Hour, Dylan's respected XM Satellite Radio (NASDAQ: XMSR) show. The theme of tomorrow's episode, the launch of the campaign, will be the Cadillac.

By now, the irony of '60s musicians cashing in on their anti-establishment image by shilling for The Man is old news. I do often wonder, though, why virtually every rock/pop song used for commercials seems to come from the '60s and '70s. Just how effective are these ancient tunes in reaching potential customers, for whom these songs are as old hat as Rudy Vallee's were in my childhood? (Yeah, I'm old.)

While Dylan has shown the courage to evolve his music gracefully, producing some of his most appealing tunes in what would be the twilight of most careers, this won't do much to enhance his image. The incongruity of attempting to use his scruffy, roots image to rebrand Cadillac seems a bit clueless. I can't imagine playing "A Hard Rain's A-gonna Fall" or a similarly mournful tune about injustice, on the CD player of a Escalade.

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