The German auto giant Daimler recently announced that it would discontinue its luxury Maybach brand, ending a decade of losses for a high-end line of cars that sell for over $350,000. The Mercedes Benz S-Class will replace the Maybach.

The loss may prove to be just as great for hip-hop — at least symbolically — as it is for the manufacturer of the Mercedes Benz. Ironically, the failed Maybach brand has become one of the most widely referenced brand names in rap. And rap artist Rick Ross even named his record label after the car.

Celebrity endorsements are a big part of the advertising world, with as many as 20 percent of ads featuring a TV, film or sports star. Nowhere is the link between celebrity and product endorsement more evident than in the black community, especially with the promotion of certain merchandise by rap artists.

Hip-hop is arguably the most influential cultural and popular music genre in America. Over the years, hip-hop endorsements — including product placements, embedded marketing, name dropping and shout-outs in rap songs and music videos — have generated a boost in sales for products ranging from athletic shoes to clothing to liquor. As a result, some consumer brands became hits among black consumers, popular especially among young urban consumers of color, even when the manufacturer did not intend to target that demographic.

Nevertheless, the track record in this regard is uneven. While the effect of rap celebrity endorsements is sometimes a positive one, these promotional efforts often backfire. And when they do, the failures can reveal a huge disconnect between the artists and their audiences in terms of lifestyle, bling and the almighty dollar.

Even in the earlier days of hip-hop, rappers promoted products of their choosing in their lyrics. The genre has long been receptive to brand name marketing. One of the more noteworthy examples was Run-D.M.C. and their hit single “My Adidas.” As a result of their efforts, the legendary rap group signed a $1.5 million deal with the sneaker company, and formed a long-term relationship with the athletic manufacturer.

Similarly, Kurtis Blow made an agreement with Sprite, becoming the first hip-hop artist to do a TV commercial. And Jay-Z’s S. Carter shoes broke ground for Reebok as one of the company’s best-selling products, and a pioneering success by a non-athlete.

Rap and alcohol have established a profitable alliance. In an aspirational genre such as rap, luxury items such as expensive liquor, wine and champagne have broad appeal. Call it conspicuous consumption, which amounts to poor folks wanting the best things in life to show others they have arrived, just like The Jeffersons. Alcoholic beverages such as Hennessy Cognac and Alizé were popularized by the hip-hop community, and young black consumers helped the bottom line of the wine and liquor industry. Biggie Smalls was likely the first rapper to mention Cristal, after singing—or rapping—the praises of Moet & Chandon Champagne. Busta Rhymes told his fans to “Pass the Courvoisier” and changed the game when his song was responsible for double-digit sales growth for the beverage in the U.S.

Then there are the rappers-turned-entrepreneurs, such as Sean “Diddy” Combs with his Ciroc vodka brand, and Pitbull with the Voli vodka label. The game is changing. Rappers have moved from rapping about the drink they’re drinking to rapping about the drink they’re selling.

However, with the successes come the glaring failures. In some cases, the manufacturer of a given product does not welcome the attention it receives in rap lyrics. The company might not want the shout out, even when it helps their bottom line. Some of this is due to class elitism and snobbery, while the rest of it is explained by racism.

Case in point: Timberland, maker of boots and outdoor apparel, which was recently purchased for $2.3 billion. The company, associated with hip-hop culture since the 1990s, has done extremely well. Yet Timberland — a hip-hop artist and producer even took the brand name as his own — is uncomfortable with the association with an urban demographic it cannot control. An employment discrimination lawsuit filed by black men against Timberland in the 1990s only made things worse. And so, a company markets to one segment of society, in this case, white, middle-class professionals, while depending on another demographic for its profits.

Another failure, Cristal, was once deemed a success story. Cristal’s attitude toward its hip-hop clientele has been characterized as ambivalent at best, and racist at its worst. When the manufacturer of the high-end champagne belittled Jay-Z’s support for the beverage — and even suggested that his support could damage the brand — Jay-Z accused the company of racism and called for a boycott of the product.

Frédéric Rouzaud, managing director of Cristal manufacturer Roederer, told The Economist that he viewed Cristal’s association with rap “with curiosity and serenity.” When asked if he thought this would harm the brand, he said, “that’s a good question, but what can we do? We can’t forbid people from buying it. I’m sure Dom Pérignon or Krug would be delighted to have their business.”

Meanwhile, Hummer, once a symbol of American excess, was the official gas-guzzling military vehicle of hip-hop until General Motors scrapped the vehicle. A casualty of the economic downturn, this SUV was a conspicuous symbol of a hip-hop bling culture that was rendered out of touch and anachronistic. At a time when blacks and Latinos are suffering an unprecedented loss of wealth, talk of Hummers seem misplaced as people lose their homes, jobs and the trappings of middle class status.

Hip-hop has revealed other blind spots as well. The multimillion dollar hip-hop apparel industry has faced accusations that it profits from Third World sweatshop labor. And Jay-Z and Kanye West faced criticism for their pro-bling Watch the Throne album in the midst of the Great Recession. Moreover, Jay-Z faced additional criticism for selling “http://www.thegrio.com/entertainment/can-rap-stars-occupy-while-watching-their-thrones.php?page=2”>“Occupy All Streets” t-shirts through his Rocawear line, yet not donating any of the proceeds to the Occupy Wall Street movement alluded to in the t-shirts.

Money changes everything. As an aspirational cultural force, rap and hip-hop always reflected the dreams as well as the realities of people who often had to do without. Nevertheless, somewhere along the way, some rap artists grew out of touch as the industry became more lucrative. Now, they appear as oblivious and inappropriate as the Wall Street executive with his extravagant bonus.

In light of the current post-bling economic realities — at a time of mass deprivation, when the public is critiquing America’s gaping wealth inequality and rejecting the excesses of recent years—rappers may need to learn to adapt, re-prioritize and remain relevant while making a buck.