American Icons on the Brink

General Motors

With its June 1 bankruptcy filing, auto giant General Motors has now effectively slid off the brink. Even so, the deal may give GM chance for new life. It is unlikely to ever again control 50 percent of the North American vehicle market and return to its peak market value of $54 billion. But with billions of government aid, reduced debt and a more streamlined production process, it may return to financial health.

NEXT: Playboy

Playboy

Once upon a time, Playboy was at the apex of the cultural zeitgeist. For generations of young men, Playboy was the symbol of everything cool and desirable. Founder Hugh Hefner has done a lot in his 83 years, including making huge contributions to First Amendment rights. But the world has changed. Now there’s plenty free adult content on the internet, as well as publications like Maxim and Blender competing for the young male demographic. This leaves Playboy with a very bleak outlook. No wonder Hef’s looking to unload the empire.

NEXT: Kodak

Kodak

Founded in 1892, Kodak, the largest supplier of photographic film in the world, has long been nearly synonymous with film and film cameras. Its Kodachrome is the most famous film of all time, and is valued for its perceived unique look. But time marches on, and we now live in a digital age. Eastman Kodak has had to discontinue many of its films, disappointing many dedicated film users. Kodak has strived to refocus its business on digital photography and digital printing, but many consider those efforts to be too little too late.

NEXT: Blockbuster

Blockbuster

After the opening of the first Blockbuster store in Dallas in 1985, it seemed like hardly any time at all before Blockbusters could be found on virtually every street corner. The video and video game rental chain offered more copies of more titles than its mom-and-pop competitors, and was family friendly too (i.e., no porn). It quickly became a multi-billion-dollar enterprise. Then along came a little thing called Netflix, with its videos by mail scheme, as well as online film providers such as Hulu.com. Blockbuster has struggled to stay competitive, but things aren’t so rosy any more.

NEXT: Six Flags

Six Flags

Between a protracted legal battle with New Orleans, the swine flu-inspired closure of its Mexico City park, and $4.2 billion in debt, it would seem that Six Flags is facing insurmountable odds. Even in the face of adversity, the company is chugging along. This summer, the chain is debuting new attractions at almost all of its parks, has expanded its operating calendar, and is experimenting with broader food options. Perhaps more importantly, it has invested $100 million in maintenance and cleanup in an attempt to address customer complaints that the parks were getting run-down and seedy.

NEXT: New York Times

The New York Times

Reasonable minds may disagree about whether The New York Times is the finest newspaper in the country. Most of us, however, can at least allow that over more than a century and a half of publishing it has entrenched itself as our national newspaper of record. But the New York Times Company, like nearly all of its rivals in newspaper publishing, is sputtering for breath in an industry that's going digital so fast that it hasn't figured out how to get paid. Yet, every month, the New York Times seems to devise new way to keep the wolves away. Question is, how long can that last?

NEXT: MGM Mirage

MGM Mirage

A long-simmering controversy over MGM Mirage's choice of development partners is just one in a long line of setbacks that has the company teetering on the edge of disaster. Even with its geographic diversity, MGM Mirage depends on Las Vegas for its table stakes, and the news there doesn’t look good. Visitorship is down, while convention traffic is off as well. With the MGM Mirage and Las Vegas Sands both in perilous shape, what are the odds are that both will be around by this time next year?

NEXT: Sears

Sears

Wall Street hailed the combination of bankrupt retailer Kmart Corp. with Sears, Roebuck & Co in 2003, and Eddie Lampert, the driving force behind the deal, was seen by many as the next Warren Buffett. Unfortunately, things haven’t quite worked out. The company, now called Sears Holdings Corp., has struggled against larger rivals including Wal-Mart and Target. Many Sears mall locations were hurt by the growth in online retailing. Plus, the company has endured the worst climate for retailers in decades, resulting in laid off workers and cost cuts. But will that be enough revive the new Sears?

NEXT: Sirius

Sirius

Remember when satellite radio seemed like the next new, unstoppable thing? That was back in the 1990s, and Sirius Satellite Radio became the home of such luminaries of the airwaves as Howard Stern, Martha Stewart, Jimmy Buffett, and Eminem. Sirius only had one serious rival, XM Satellite Radio, with which in the fullness of time it merged to become Sirius XM Radio. Its receivers were available in every auto make from Dodges to Jaguars. It even dabbled in internet radio and TV. The only thing it didn’t seem to do was make a profit. Sirius dodged bankruptcy in February, but for how long?

NEXT: Sbarro

Sbarro

No restaurant chain in the country is more associated with serving red-sauced, parmesan-sprinkled favorites to the masses than Sbarro. But after decades of worldwide expansion, the company, founded by an Italian immigrant family in Brooklyn half a century ago, faces the prospect of having to cool its ovens for good. Sbarro's fate is largely tethered to the success of shopping malls, which have been devastated by the economic downturn. The company also has higher debt and less cash flow than competitors Domino's and Pizza Hut. Can Sbarro ride out the recession? The outlook doesn't look appetizing.

NEXT: Citigroup

Citigroup

In 1998, banking behemoth Citicorp joined with financial giant Travelers Group in what was one of the world's largest mergers. The result? Financial services giant Citigroup, which boasts one of the world's largest financial services network. So what went wrong for Citigroup? Misplaced trust, greed, loss of good bankers, a poor understanding of the banking business, or bad risk management? The firm has made many mistakes, as have many other investment banks. But to simply blame Citigroup's misfortunes on the economic crisis (that it helped create) is a gross oversimplification.

NEXT: Saks

Saks Fifth Avenue

With its iconic flagship store on Fifth Avenue in Manhattan and his-and-hers stores across the street from each other on Chicago's swank Magnificent Mile, Saks has long been one of the landmarks of luxury retail. But like many high-end retailers since the recession hit, Saks has suffered from a big pullback in consumer spending that may prove to be less of a symptom of the economic downturn than a characteristic of a new reality that doesn't include $600 shoes. Yet, despite a dismal holiday shopping season last year, Saks remains committed to being a luxury player.

NEXT: Clear Channel

Clear Channel Communications

Just nine months after being acquired in a $27 billion leveraged buyout, radio and billboard giant Clear Channel Communications has begun reaching out to lenders about restructuring the company's massive debt load. The company has been buffeted by the slowdown in advertising spending, and analysts watching the company suspect it could violate its loan terms later this year. What Clear Channel has in its favor is that it owes senior lenders $16 billion of its $18 billion in long-term debt, so the lenders may not be interested in forcing a bankruptcy.

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