This post is part of our feature on Money Losers of 2008. See all 20.

It's hard to dispute the fact that 2008 has been a lousy year for singer/actress, Jessica Simpson. She entered the year with her new beau, Tony Romo of the Dallas Cowboys, and was immediately blamed for his troubling performance on the field. The release of her feature movie, Blonde Ambition, went straight to DVD without even blinking. Her debut into the country music realm has all but fallen flat. The kindest professional critique of her maiden country album, Do You Know, referred to that effort as "solid yet simple." The reviews go steeply downward from there.

In defense of the minx with the jinx, I think Jessica Simpson has been mistreated a bit. I mean, blaming her for the flat performance of Romo's Cowboys just isn't fair. But then again, we Packer fans know that those Cowboys are just loaded with handy excuses. It's just a powerful shame that they had to make Jessica Simpson one. Perhaps it's due to the shock of no longer finding Brett Favre at Lambeau Field.

As far as Jessica Simpson's acting career, I thought we had settled that issue with The Dukes of Hazard. As a matter of fact, I thought we settled it with her Pizza Hut commercial. You know, that's the commercial where they made her come out and say "Hi, Yaw" as if it was something she would normally say. Worst of all, they used the cut where her telltale neck tick makes her whole head jerk to the side. I suppose I need to reissue my "Jessica is not an actress" memo to Hollywood.

In the wake of her divorce from ex-98 Degree hunk Nick Lachey and the disappointing box office showing of Dukes of Hazzard, a noteworthy debut for her latest movie, Blonde Ambition, was just what the former pop princess needed.

But this was not what the doctor ordered. The movie was thought to be headed for direct to DVD release but they decided to give it a shot in Texas theaters. It grossed $384 in its opening -- $48 per screen, 6 people per showtime, and a total of 48 viewers.

Ouch. They could blame the fact that the movie has been available for illicit download online for weeks, but that only garnered 6000 viewers -- who could watch it at home. On their computers. For free.

After reporting a disappointing decline in second-quarter earnings and sales last week, Macy's (NYSE: M) is pulling out the big guns. Donald Trump and Martha Stewart are just two among a coterie of celebrities being employed in the department-store company's $100 million advertising blitz.

New television spots for Macy's - one of which will debut on September's Emmy-Award broadcast - will also feature R&B singer Usher, Tim Gunn from Project Runway, chef Emeril Lagasse, and hip-hop mogul Sean "Puff Daddy" "P. Diddy" "Diddy" Combs.

Also on the roster as a celebrity endorser for the Cincinnati-based retailer is Jessica Simpson. Seems like a bit of a slap in the face to hometown boy (and erstwhile Simpson paramour) Nick Lachey.

Stewart, figurehead of Martha Stewart Living Omnimedia (NYSE: MSO), also is working with Macy's on an exclusive line of Stewart-branded home products, which will launch this fall only in Macy's stores.

Beth Gaston Moon is an analyst at Schaeffer's Investment Research.

Shares of Parlux (NASDAQ: PARL) are up around 16% today on just one bit of news. No, the company didn't report a great quarter, and no private equity firm has made a bid. Instead, the manufacturer and market of perfume lines including Maria Sharapova, Paris Hilton, and Royal Copenhagen has signed a deal with Jessica Simpson to launch a fragrance bearing the former Newlyweds star's name. Financial terms have not been disclosed, and that's a key point for investors to remember.

In licensing deals, most of the benefit of the name aggregates to the owner of the name. Ms. Simpson will likely receive a hefty chunk of the profits from the product's sales, leaving Parlux in a manufacturing, marketing, and logistics role. As exciting as all the company's lines are, Parlux has lost money over the last 12 months, and its stock has plunged from an all-time high of over $16 to its current price of around $5.20. Interestingly, the stock hit a 3-year low yesterday.

I'm surprised at how positively the market is reacting to this bit of news. In the wake of her high-profile split with Nick Lachey, the flop of Dukes of Hazzard, and her last album A Public Affair, most of the headlines she's generated lately have been about her relationship with John Mayer.

As one Amazon.com reviewer put it, "Her 15 minutes are ticking." For now, the Jessica Simpson deal is helping sell Parlux stock. But will she be able to sell Parlux perfume?

Rolling Stone magazine recently published a fortieth anniversary issue celebrating the magazine's tenure in the popular culture business. After reading the issue and wading through the multitude of advertisements, I started thinking about Rolling Stone as the precursor to so many of the music magazines in existence today and how these kinds of media serve the record industry in an increasingly digital world. Forty years ago, Rolling Stone may have been an inventive method to sell music, with interviews and features about artists, but as it is now the magazine and its followers are hardly what they claim to be: music magazines.

The very notion of a "music magazine" is quickly becoming outdated, as is found simply by perusing through the articles and features through most of the print I purchase regularly. Compare it to other, older magazines, like the British NME and you will find that the Rolling Stone falls down in coverage simply because there is an overabundance of non-music advertisements. Even other contemporary magazines, like Blender, manage to advertise the actual music, while both sell the digital devices that are quickly becoming the mediums of music transferal.

If championing the music is the goal, which presumably it is, Rolling Stone has never seemed far from what we call "mainstream," so it hardly has the capacity to introduce new bands and compete with the growth of online services like Google Inc. (NASDAQ: GOOG)'s YouTube or News Corporation (NYSE: NWS)'s MySpace. Even other magazines quickly champion lesser known bands into mass-popularity. Consider NME, the magazine was a massive supporter of the Arctic Monkeys and they quickly became more popular than they had been, even with the online support. With the weekly issue NME prints, the publisher keeps a more up-to-date and consistent online news service, signaling that the move online is not contained to artists.

The Kentucky Derby is, without a doubt, the most exciting horse racing event of the year. Millions of people who don't even watch horse racing pay attention to it, and it's featured all over the news. With all the coverage and excitement surrounding the race, it may be tempting to place a bet on it. Heck, even Jessica Simpson won a few dollars betting on it a few years ago on an episode of her show The Newlyweds (Sadly, I lost a pretty penny betting that their marriage would last more than five years).

But here's the best advice I can give you regarding the Derby: Don't bet on it. As the most-watched race of the year, you won't have any edge -- there's too many other experts watching it. In his book Picking Winners, horse-betting expert Andy Beyer advises readers to "Only go to tracks where there aren't a lot of good players so you can clean up."

What does this have to do with investing? Following Beyer's logic, it is also unwise to invest in stocks like ExxonMobil Corp. (NYSE: XOM), Goldman Sachs Group (NYSE: GS), and Wal-Mart Stores (NYSE: WMT). There are simply too many good players handicapping these stocks for us to be able to find good deals. Remember: In horse racing, the object is not to bet on the horse most likely to win: That will nearly always be the favorite. The object is to bet on the horse that offers the best risk/reward ratio -- the horse that has a better chance at winning than its odds would indicate. This is a market inefficiency, and it's more likely to be found in small-caps or small tracks than big-caps or big tracks.

This post is part of our Battle of the Brands feature. Let us know which brand you prefer, and watch out for more Battle of the Brands posts.

I'm not ashamed to admit that I've been known to turn up my nose at (free) pitchers of Miller Lite, exclaiming "this [potential explicative] stuff taste like formaldehyde!" Many of my closest friends and family members, however, prefer the "tastes great/less filling" brew to any from Anheuser-Busch (NYSE: BUD). Though everyone is entitled to his or her own opinion, when it comes to the battle of the light lagers, I don't go quietly into the night with this one. Maybe it's because I was born and raised in St. Louis, which would arguably cease to function without BUD dollars. Maybe I simply prefer red to blue. Or perhaps it's because I'm not a huge fan of tasting formaldehyde (I kid!). Regardless, I stand my ground for my right to drink Bud Light, demanding it for shared pitchers and community coolers. In fact, I haven't even tasted Miller Lite in about seven years, but more on that later.

Celebrity Backers: "H.O.V.A." vs. the Nicest Divorced Guy in America

From the real men of genius to the man-law round table, both BUD and SABMiller (LSE: SAB), the London-based parent company of the Miller Lite brand, are powerful forces in the advertising business, and celebrity endorsements continue to roll in. Rap artist Jay-Z emerged from retirement ready to pitch Budweiser Select (a low-carb, 99-calorie offering) while Burt Reynolds, Jerome "The Bus" Bettis, and others sit on Miller's aforementioned round table. While not lending an endorsement in a traditional sense, who can forget Nick Lachey and Jessica Simpson frequently kicking back with ice-cold cans of Miller Lite on the now-defunct (in every-which-way) Newlyweds? The brand allegiance added to Lachey's corn-fed all-American appeal (and I say that honestly as a BUD fan).