Some people saw the entire stock market mess coming years ago. Congrats if you're one of them. For those of us still trying to pick our chins up off the table, the number of companies that died (or practically did) in 2008 is staggering. In the finance world, the turmoil claimed:

  • Countrywide
  • Bear Stearns
  • Freddie Mac
  • Fannie Mae
  • Lehman Brothers
  • AIG
  • Washington Mutual

It's been a bloody year for many companies. Which might be next on the chopping block in 2009? These five top my death watch list.

Citigroup (NYSE:C)
Financial institutions had written off about $760 billion in bad assets through September, yet the International Monetary Fund predicts that number could eventually swell to $1.4 trillion. Dr. Doom himself, Nouriel Roubini, thinks the figure will be closer to $3 trillion, meaning we could be just a fraction of the way through asset writedowns.

How much of that impending slug of bad debt do you think sits on Citigroup's books? I have no idea, and to be fair, it's less today than it was before the government insured $300 billion of Citi's assets. But with a company that has more than $2 trillion in assets supported by just $36 billion in tangible common equity, and which had to be bailed out twice in six weeks, I doubt it'll take much more than a stiff breeze to send Citi over a cliff.

General Motors (NYSE:GM)
As Congressman Ron Paul (R-Texas) said recently, "I am afraid the American auto industry will soon learn that having billions rain down from Washington will not be the blessing one might expect."

Agreed. Some simple math here: GM is currently burning through around $5 billion per month. To plug the hole, it's asking the government for $18 billion. By my calculations, that might get the company through Easter. Tops.

To be fair, no one expects the $18 billion to be a one-time fix, and GM will hopefully start slashing costs like there's no tomorrow (literally). Still, I think reality will eventually set in, and one of two scenarios will play out:

  • The amount of money it'll take to save Detroit will become so large that current shareholders will be wiped out.
  • It will become apparent that saving GM will require throwing too much good money after bad, making a government-assisted bankruptcy look like more of a viable option.  

If you're dead set on an auto rebound, Ford (NYSE:F) is probably a better bet. After mortgaging $18 billion of assets in 2006, it's probably the strongest among the Big Three. Of course, that's not saying much.

Sirius XM Radio (NASDAQ:SIRI)
With a $1 billion-plus debt load coming due in 2009, a few hundred million in cash, and a market so paranoid that even Berkshire Hathaway's (NYSE:BRK-B) chances of survival have been in question, options seem to be running thin for Sirius.

As fellow Fool Rick Munarriz pointed out earlier this week, experimenting with a monster reverse stock split might give it some flexibility. But that's such a Hail Mary strategy that current shareholders have to wonder what's left for them. With a current market cap of less than $500 million, raising a meaningful amount of cash seems more like wishful thinking than anything.

Level 3 Communications (NASDAQ:LVLT)
As one of my Foolish colleagues, tech maven Tim Beyers, recently told me regarding this debt-laden company, "Winning business, but sheesh, what a mess that balance sheet is. An above-average product, for sure, but this market is so tenuous that it's tough to walk this sort of financial tightrope."

Admittedly, "death" might be too strong a word to use here -- especially since so much of the company's debt doesn't come due for several years -- but you really have to wonder about companies that put so much faith in leverage, based on assumptions about an economy that could be a wee fraction of its former self in the future. And with shares trading at under a buck, good luck raising new equity.

Cemex (NYSE:CX)
This one's about as hit-or-miss as it gets. Shares tumbled last week, after the cement giant was able to roll over only a fraction of the debt it had planned on. But the stock surged days later on word that debt negotiations were moving right along.

Sure, those negotiations could get this company through 2009 -- but then what? An infrastructure company with more than $16 billion in debt, facing what could be a multiyear global slowdown, is a dubious proposition. If global infrastructure projects boost Cemex's bottom line in 2009 and debt is seamlessly rolled over, investors are probably A-OK. If not, and the Mexican government is forced to intervene … well, ask Fannie and Freddie shareholders what happens when the government saves the day.

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Fool contributor Morgan Housel owns shares in Berkshire Hathaway. Cemex is a Motley Fool Global Gains selection. Berkshire Hathaway is a Motley Fool Inside Value pick. Cemex and Berkshire Hathaway are Motley Fool Stock Advisor selections. The Fool owns shares of Cemex and Berkshire Hathaway. The Motley Fool is investors writing for investors.