not your stereotypical 50-year-olds. They are younger in mind, body, and spirit than generations before them, and the picture of rocking back and forth in a rocking chair is something they reserve for people in their eighties. These midlifers remember Woodstock (or at least have some evidence that they were there) and have kept classic rock as part of their lives. It explains why the Rolling Stones, Elton John, and Neil Diamond thrive on tour.   Connecting with Boo mers   Nothing establishes an extrasensory connection with baby boomers more effectively than the songs and bands they loved during puberty and early adulthood. "Music defines a generation, and who could better represent or influence boomers than rock stars who are mostly baby boomers themselves, like the Rolling Stones and the Eagles," says Stephen Swid. Some people still get the urge to gulp a Coke when they hear "Id Like to Teach the World to Sing." What defines them as a generation defines them as a market to advertising, mar- keting, and brand managers.     Sheer size, spending power, and accessibility make the baby- boomer market extremely attractive to all kinds of marketers, even those who previously sold products to a different generation of con- sumers. Penetrating a new market, however, means brand rejuvena- tion and repositioning, even if the brand is, arguably, one of the best known of the previous century. We refer, of course, to Cadillac, the brand that went from status symbol to age identifier-becoming known as the wheels of choice for oldsters around the country. Sim- ilar to the Rolling Stones, Cadillac faces the challenges of: S Evolvingitsproductataratethatdoesntalienate current fans but positions it as fresh among baby-boomer markets S Creatinganemotionalconnectionwithandharnessingthebuy- ing power of baby boomers to grow profits S Relatingtothechangingattitudesandlifestylesofitscustomers Since the inception of the Cadillac brand, culture and mass- market values have changed, due in part to the likes of Elvis and the Rolling Stones. Conventional behaviors, attitudes, and style of sixty- somethings indicate that Jagger, Richards, Watts, and Wood should be sporting cardigans and taking quiet walks with grandchildren. Whereas the Rolling Stones shattered the traditional image of what it means to be 60, Cadillacs brand only furthered it. The more people adopted a youthful mind-set, the greater the disconnection between Cadillac and the baby-boomer market became. To bolster sales, create a new generation of fans, and increase profits, Cadillac would have to position itself as a lot more Rolling Stones and a lot less rocking chair.