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As Cadillac heads down the road, what kind of music is on the stereo?

The GM luxury division’s “Break Through” television ad campaign defibrillates viewers’ hearts with Led Zeppelin’s 1971 classic “Rock and Roll.” Let’s not kid ourselves–this ad campaign is aimed primarily at white boomers.

Yet Cadillac’s biggest fans are at the other end of pop culture’s radio dial. According to a survey by San Francisco-based marketing analyst Lucian James, Cadillac became the most name-dropped brand in songs on Billboard’s Top 20 chart in January 2004, overtaking Mercedes-Benz, which has long been hip-hop’s symbol of bling-bling materialism.

In Los Angeles in February, GM staged the “All-Star Showdown,” a charity event at which prominent athletes and celebrities–including Shaquille O’Neal, Busta Rhymes, Public Enemy and Martin Lawrence–competed for the title “King of Bling” with their pimped-out Cadillac Escalades and Hummer H2s.

Five years ago, Cadillac was about as hip as wingtips. Today, the brand is on the bleeding edge of what’s cool, a fixture in urban music and cherished ride of some of the nation’s biggest superstars.

“It’s been a totally great surprise,” Cadillac General Manager Mark LaNeve told Automotive News. “In terms of generating anything that is targeted to that group, no, we can’t take credit for it. We’re too busy to know what’s cool.”

Cadillac now finds itself curiously suspended between two demographics with very different sensibilities. For all the talk about hip-hop going mainstream and crossover hits such as OutKast’s “Hey Ya!” you are not going to find white middle-aged soccer moms swapping out their Sting CDs so they can rattle windows with Youngbloodz’s “Cadillac Pimpin.”

The rise of Cadillac in hip-hop culture begins with the American bluesmen of the mid-20th Century at a time when the name Cadillac was the definition of excellence and the cars were automotive totems of the ruling class.

Flash forward to 1968 and the birth of funk, with James Brown’s black identity anthem “Say it Loud.” The blues’ covert sexuality gave way to funk’s explicitness, as in Brown’s “Sex Machine.” The exuberances of funk fashion morphed into the dandified “pimp” style favored by the crushed-velvet, gold-toothed sex entrepreneurs we would now call “playas.”

And Cadillac was along for the ride.

Ron O’Neal’s “Superfly” character, though not strictly a pimp, has the look, from floor-length trench coat to massive gold-grilled Cadillac Eldorado.

But a funny thing happened on the way to the 21st Century: Pimpin’ went mainstream.

Consider MTV’s new show, “Pimp My Ride,” hosted by Xzibit, or Spike TV’s “Ride With FunkMaster Flex,” which follows the hip-hop DJ as he visits celebrities’ “illest” custom jobs.

For Cadillac, the tipping point came with the 1999 introduction of the Cadillac Escalade, a full-size SUV (based on the Chevy Tahoe) loaded with luxury and trimmed out with dramatic, knife-edge styling.

Suddenly, players had a new Cadillac. The ‘Slade quickly became the image ride for the brand-obsessed hip-hop culture. In 2003, Cadillac’s truck sales–Escalade, ESV, ETX, SRX–grew almost 20 percent over the previous year, while its car sales were flat.

But more important than per-unit profit is the priceless exposure for the Cadillac brand in a trend-setting demographic it could never have thought of reaching on its own.

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Edited by Cara DiPasquale (cdipasquale@tribune.com) and alBerto Trevino (atrevino@tribune.com)