Celebrities in the Corner Office: The Best and Worst Business-Star Duets

Product endorsements by famous people are one of the most tried-and-true marketing gimmicks out there, and with good reason. In our fame-obsessed culture, what better validation is there of a product than a celebrity who likes, uses, and endorses it?

Lately, though, celebrity endorsements gone a step further. Positions once usually held by established business executives -- e.g., creative director, majority shareholder, and even co-founder -- are now beginning to be filled by well-known actors and musicians. In some cases the results are fantastic. In others... not so much.

Here are some victors and victims within the realm of celeb-company collaborations.

Winners: Will.i.am and Intel

It seemed like an odd pairing when in 2011 Intel (INTC) appointed the front man for pop/hip-hop group The Black-Eyed Peas as its "director of creative innovation." The music star was better known for jumping around in music videos with Fergie than for any particular expertise with semiconductors and computer connectivity issues.

However, Will.i.am took his Intel title and enthusiastically ran with it. He attended meetings and conferences, proudly brandished his Intel employee badge, and pitched ideas to company bigwigs. Specifically, Will (or is it Mister I.am?) has collaborated on designs that fuse art and music seamlessly with technology. This includes working to further Intel's "compute continuum" concept, which helps devices compute and connect to the Internet.

Apparently, Will.i.am has been bitten by the corporate collaboration bug. He was recently named chief creative officer of 3D Systems (DDD) (currently the largest company within the 3-D printing industry). Since Will.i.am has already made a music video in which he 3-D printed his own head (check out the footage at 1:38 here), expect a collaboration that, if nothing else, is fascinating.

Losers: Lindsay Lohan and Emanuel Ungaro

The career of Hollywood bad girl Lindsay Lohan has been marked by so many bizarre scandals that it's easy to forget that, in 2009, fashion house Emanuel Ungaro appointed the troubled actress to be its artistic advisor.

The clothing line had been working to reinvent itself since Ungaro himself retired in 2005. Lohan's job was much more than being the promotional face of Ungaro. The actress, who had little-to-no previous fashion design experience, was tasked with creating an entire season's worth of clothing. She worked with Spanish designer Estrella Archs to design the company's spring 2010 collection, which was full of bright neon colors, miniskirts, and heart shapes.

The collection was -- to put it mildly -- roundly panned, and Lohan was soon dumped by the fashion house. Still, she still managed to win over a client or two. Stephanie Solomon, fashion director at Bloomingdale's, admitted to buying a few pieces from the line, believing they would appeal to a younger audience.

Winner: Dr. Dre and Beats by Dre

You might have thought that legendary rapper Dr. Dre already had his hands full with recording albums, writing hits for the likes of Eve and Gwen Stefani, and discovering artists like Eminem and 50 Cent. But in 2008, Dr. Dre added entrepreneur to his list of titles, collaborating with Jimmy Iovine, chief of Interscope Records, to create a line of headphones.

%VIRTUAL-article-sponsoredlinks%Beats by Dre started out as a small company. Its mission, in the company's own words, was to help "a new generation of unsuspecting music fans finally know what bass sounds like!" It's gone on to become one of the biggest brands in the $1 billion premium headphone industry, reportedly (as of 2012) commanding a 51 percent market share.

Dre and company has opened its doors to even more celebrity and big-brand collaborations. Justin Bieber and Lady Gaga have helped design their own products for Beats. The company worked with Hewlett-Packard (HPQ) in 2009 to create the HP Envy notebook. And in 2011 the company hit a big milestone, selling 51 percent of Beats to telecom company HTC for a healthy sum of $309 million.

Next on the rap icon's list: a streaming music service, BeatsMusic, which launched on Jan. 21. Watch out, Pandora (P) and Spotify.

Losers: Justin Timberlake and MySpace

To his credit, Justin Timberlake has already accomplished the seemingly impossible with his career -- breaking free of 'N Sync and becoming a respectable solo pop star and actor. Beyond that, though, Timberlake also has several successful corporate endorsement deals under his belt, having recently been a rep for both Anheuser-Busch's (BUD) Bud Light Platinum and Callaway (ELY) golf clubs and accessories.

Lending your handsome face to a product's advertising campaign is one thing. Having a stake in a company is a whole different kettle of fish.

In 2011, Rupert Murdoch's News Corp. (NWS) sold Facebook's imploding predecessor Myspace for a paltry $35 million. (It was quite a fire sale given that Murdoch purchased the company in 2005 for $580 million and watched its valuation rise in 2007 to a staggering peak of $65 billion.)

The buyers, Specific Media Group and Timberlake (although the size of his stake has not been disclosed), saw Murdoch's loss as an exciting possibility. Their vision was to turn the floundering social media company into a Netflix (NFLX)-style go-to spot for original programming, music videos, and new songs and albums.

So far, all that ambition has led to a glitzy relaunch party, a $20 million advertising campaign, and a number of layoffs (paring down 5 percent of Myspace's staff).

As of October 2013, Myspace reported having 36 million users, which was a 50 percent boost from the the 24 million users it had to its name in pre-launch January. That kind of growth might be promising, but it's still nowhere near the company's 185 million user base of 2007. It's possible that Justin might have gotten a little in over his head with this one.

Motley Fool contributor Caroline Bennett has no position in any stocks mentioned. The Motley Fool recommends Pandora Media. It recommends and owns shares of 3D Systems, Intel, and Netflix. Try any of our Foolish newsletter services free for 30 days.