As a recent arrival at the Fool, and a proud pop-culture aficionado, I've come to realize that investing and pop culture share an interesting intersection: media advertising. I'm not talking about the latest viral Web phenomenon; I mean good old-fashioned TV and magazine ad campaigns. Ads can have a tremendous, almost immediate effect on how potential customers perceive a company -- and in time, that perception can work its way to the company's bottom line, its stock price, and its standing in your portfolio. Just ask Gap (NYSE:GPS), which is hoping to revitalize its flagging sales and image with two distinctive new ad campaigns.

Orwell in the computer store
Still doubtful that a single ad could change a company's fortunes? It did for Apple (NASDAQ:AAPL), whose "1984" spot is one of the most famous ads ever. The commercial opens with an auditorium of people bowing before a Big Brother figure on a massive screen. A woman runs into the auditorium, chased by police figures. She hurls a hammer at the screen and shatters the TV, and as the audience is bathed in light, a voiceover announces, "On Jan. 24, Apple Computer will introduce the Macintosh. And you'll see why 1984 won't be like '1984.'"

In 30 seconds, Apple referenced a classic work of literature, tantalized millions, and heralded a new age of technology. Of course, not all ad campaigns manage to say as much about a company's direction, but the introduction of the Target (NYSE:TGT) bull's-eye, the catchy list of ingredients for McDonald's (NYSE:MCD) Big Mac, and Lee Iacocca's plain-spoken Chrysler (now DaimlerChrysler (NYSE:DCX)) spots were all spirited ways in which established companies recaptured the public's attention. In Chrysler's case, they helped save the company.

With two high-profile ad campaigns in recent weeks, will Gap be able to achieve the same results?

The conquest of khakis
Back in the early 1990s, Gap launched a simple advertising campaign: a photograph of an artist or writer who rose to fame in the 1940s or '50s, with the tag line "(Insert name here) wore khakis." Memorable icons included Jack Kerouac and Allen Ginsberg, and the campaign was effective in its simplicity and daring. (Kerouac may have worn khakis, but he didn't buy them at the not-yet-existent Gap.)

While the stock price bounced around the high $20s to mid-$50s during the mid-'90s, the company had positively captured the public's attention. Saturday Night Live had a popular recurring sketch about "The Gap Girls," and Sharon Stone caused a frenzy by wearing a Gap turtleneck to the 1996 Oscars. Young professionals flocked to the stores in search of the career staples: black pants, khakis, and button-down shirts.

A decade or so later, Gap has returned to ads featuring famous folk for the second phase of its three-pronged fall ad campaign. (The first campaign, focused on jeans, was launched in July; I'll discuss the third shortly.) This time, all the celebrities involved are alive, well, and shilling T-shirts. Mia Farrow, Jeremy Piven, Common, and a host of other actors and musicians are represented in photographs or drawings, with different tag lines -- "Your creation," "Your style," "Yourself," "Your silence" -- on each ad. The pictures are arresting: a vivid watercolor of an actress, a singer tearing his shirt so ferociously he exposes a nipple. On every other page of this multi-page ad insert is a T-shirt logo with the words "The Gap T-shirt Shop."

Gap also gets points for including celebrities who can appeal to customers of all ages and artistic tastes, with an impressive range of achievement and genres represented. But looking at someone else's idea of creativity is a far cry from expressing your own.

Funny face, heavy metal
Of course, as the third campaign shows, it's possible to take creativity too far. If you've ever wondered how well Audrey Hepburn and rock band AC/DC would mix, well, if you watch TV in the next month, there's a decent chance you'll find out. To promote its "Keep It Simple" campaign, featuring skinny black pants, Gap has digitally plucked an appropriately dressed Hepburn out of a dance sequence from Funny Face and set her routine to "Back in Black." Apparently, using dead celebrities to sell clothes they likely never bought from the specific retailer is in vogue every 15 years or so.

Aside from the obvious question of taste, will the Hepburn commercial succeed? Or will both it and the T-shirt ads be seen as two more ill-fated attempts at brand reinvention?

Gap entered this decade with problems relating to debt management and cash flow, as well as short-term problems managing inventory. While these issues were solvable, and the stock price and lead management team were both in the company's favor, outside forces conspired against Gap. In 2000, Swedish clothing behemoth H&M opened its first U.S. store, which was an instant hit. By offering both trendy and professional clothes at low prices, H&M appealed to Gap's consumers. With a well-planned rollout of domestic stores -- beginning in the Northeast and moving south and west -- new H&M stores are still eagerly welcomed by in their chosen cities six years later. To further boost its buzzworthiness, H&M has partnered with well-known designers to offer specially priced collections. On the domestic front, Wal-Mart (NYSE:WMT) and Target have stepped up their clothing departments in the past few years, and Gap's little sister, Old Navy, has become increasingly savvy in presenting trendy, varied styles each season.

H&M arrived in the States as a virtually unknown quantity; likewise, when Wal-Mart and Target decided to focus on their fashion departments, both companies were essentially starting with blank slates in terms of national consumer awareness. Old Navy had made a favorable if subdued impression as an adventurous, cheaper Gap, so it wasn't too alarming for shoppers if that brand experimented with trends. But the Gap had made its name with khakis and turtlenecks, and in its attempt to match H&M in terms of trendiness and fresh merchandise, the retailer gave itself an identity crisis. Longtime Gap customers didn't go to the store for gaucho pants and ponchos, and teenagers looking for those clothes didn't associate them with the Gap. Furthermore, consumers began to complain about the fabrics and quality of these new items, especially given their price points. Why pay $80 for a well-made, modern coat at the Gap when Target had an identical piece for $40?

Back to basics
If the Gap has been unable to shed its "mecca of simplicity" image for the past 37 years, I'm inclined to think that the company is stuck with it -- but Gap may be the last to agree. After all, even the fashion glossies use Gap basics like T-shirts and tank tops in their monthly fashion spreads. And in an increasingly chaotic market crowded with built-to-trash clothing, is it really the worst thing to be known for well-made basics?

The fall campaigns look to be the retailer's high-profile return to its roots. After several years of overreaching and false starts, returning to basics -- albeit in a splashy, stylish manner -- may be the savviest move the company can make. That said, I doubt the Audrey Hepburn campaign will be a winner; it's too much of a leap to connect the actress most associated with a little black dress with pants, even black ones. But the pants themselves look promising, and the T-Shirt Shop is a well-considered return to the company's roots. Now bring back some writers in khakis, and we're in business.

Bridge the gap with further Foolishness:

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Gap is also a Stock Advisor selection.

Fool online editor Sarah Erdreich used to have the Jack Kerouac khaki ad taped to her bedroom wall, but she does not own stock in Gap. The Fool's disclosure policy is cooler than any ad campaign.