Raised on Total Request Live, wireless phones, and generous allowances, generation Y is driving enormous, recession-proof sales for brands like Pepsi, Sony, and Abercrombie & Fitch. So it's not surprising that the nation's 18- to 24-year-olds are attracting the attention of all sorts of brands -- young and old, hip and stuffy alike. One unlikely suitor: the old-line car company.

Earlier this year, both DaimlerChrysler and Toyota announced plans to court the youth market that's currently infatuated with rivals Volkswagen and Honda. The new Chrysler Crossfire and Toyota Scion series -- sleek, unconventional, and decidedly strange -- aim to attract first-time car buyers with comparatively low prices and high technology. Hook 'em while they're young and impressionable, and you've got a lifelong fan. Or so the saying goes.

But how can a 78-year-old brand like Chrysler, best known for its family-friendly Town & Country line, entice a 2002 college graduate to consider its latest model over a VW Beetle? Increasingly, the challenge of winning over generation Y is falling not to traditional ad shops and 30-second TV spots, but to hybrid branding agencies with integrated marketing schemes -- not to mention super-fly names like Hypnotic, Fresh Machine, and Critical Mass.

"Young people are suspicious about marketing -- as they should be," says Rick Bolton, founder of Los Angeles-based Fresh Machine, the "next generation consultancy" that's helping Toyota launch its young, urban Scion brand. The skepticism and distrust of young consumers is driving marketers like Bolton to reconsider and reinvent the timing, placement, and goals of branding initiatives.

As Maxim would say, Sexy: Online driving simulations, branded films, over-the-top customization. Stodgy: Celebrity endorsements, closed-track demonstrations, showrooms. Nothing is sacred.

It's too early to measure the success of these unconventional branding campaigns -- their ability to convert pop-culture cachet into car sales. But it's not premature to say that traditional car companies are taking some formidable risks along the way to wooing a new generation of drivers. Here, we examine three crucial, revolutionary branding campaigns spearheaded by aging automobile manufacturers that are seeking the fountain of youth: Chrysler, Mercedes-Benz, and Toyota.

Crossfire, Cross-Sell

DaimlerChrysler has a lot riding on the Crossfire, its polished concept coupe scheduled for release in mid-2003. The first love child of Germany's Daimler-Benz and Detroit's Chrysler Corp., the Crossfire represents the potential and profitability of a momentous automobile-industry merger. Can this mega car company successfully combine sleek European engineering with classic American stylings? In many ways, DaimlerChrysler hopes the Crossfire will convince critics that it can -- and will.

But no matter how Euro-cool, the Crossfire will surely fail if it doesn't make a huge consumer splash. That's where Hypnotic comes in.

A Los Angeles-based startup, Hypnotic is an entertainment production company that uses independent films to market a variety of brands. Its challenge from Chrysler: Create a marketing campaign for the Crossfire that balances brand and entertainment, that will outlive competitors' flash-in-the-pan gimmicks, and that can extend into movie theaters, magazines, television, radio, and dealerships. And launch it a full year before anyone can buy the car.