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Ever since the credit crunch and Great Recession KO'ed the IPO market, it has been difficult for companies to raise money and go public. Perhaps the successful (and over-subscribed) IPO of General Motors (NYSE:GM) can mark the turn in the tide. Then again, a successful IPO is no guarantee of a long run as a successful company or stock; the IPO frenzy of the 1990s, for instance, created a great deal of excitement and small fortunes for nimble traders, but also left a lot of wreckage. (To learn more, see our IPO Basics Tutorial.)

Nobody knows whether General Motors will fare better on its second trip around the track. In the meantime, here is a look at some memorable IPOs that failed, flopped or otherwise flamed out.

IN PICTURES: 10 Biggest Losers In Finance

CIT Group - The Biggest of the Bunch
CIT Group (NYSE:CIT) has a history stretching back to 1908 and has boasted of having done business with about 80% of the Fortune 1000. That did not prevent the company from running itself into trouble in late 1999, and management had to scramble to find emergency credit facilities. Eventually the company sold itself to Tyco in 2001, and Tyco then spun the company out in an IPO in July that raised $4.6 billion 2002. The credit crisis walloped the company, though, and the company ultimately needed over $2 billion in TARP bailout money - a bailout that ultimately went for naught as the company declared bankruptcy in November of 2009. All that said, the company is still here; CIT emerged quickly from pre-packaged bankruptcy and trades on the NYSE once again with over $8 billion in market cap. However, bad memories for those who held the stock into the bankruptcy persist.

Can't Spell Failure without "e"
It probably will not surprise long time investors to see some famous e-commerce names on this list. Although Webvan, eToys and Pets.com were not large IPOs at the time ($375M, $166M and $83M, respectively), the stocks subsequently soared in the e-commerce/tech bubble of the late 1990s and became exhibits of the excesses of speculation.

Webvan went public in late 1999 on little more than hope. The stock doubled on its first day and the company quickly earned a $6 billion valuation, even though the company had less than $5 million in revenue and it cost over $27 to fulfill an order. The company flamed out quickly; going bankrupt in 2001.

eToys and Pets.com likewise failed quickly. Pets.com debuted on February 9 of 2000 and declared bankruptcy less than 300 days later. eToys took a bit longer to fail, going public in May of 1999 and declaring bankruptcy at the end of February in 2001. Some of its assets still exist as part of Toys R Us, but the company never came close to delivering on the hype. (To learn more, see Market Crashes: The Dotcom Crash.)

Too Little Energy to Make it
Energy has also had its share of notable flame-outs. VeraSun and Aventine were born in the ethanol boom of the mid-00's, both going public in June of 2006 and raising $420 million and $389 million respectively. Investors failed to appreciate how much competition there would be, to say nothing of the inherent difficulties of running a refining business. Both companies have since gone bankrupt. VeraSun bowed out in October of 2008, while Aventine failed in April of 2009.

Mirant (NYSE:MIR) also belongs on the list. The company's September 2000 IPO raised over $1 billion as part of its spinoff from Southern Company (NYSE:SO). Mirant never saw the high electricity prices that many expected in the 00's, though, and it soon crumbled under the weight of its debt and the industry-wide taint of Enron. The company declared bankruptcy in July of 2003, before reemerging in 2005, struggling some more and then agreeing to a merger with Reliant. They renamed the combination Genon Energy (NYSE:GEN).

Other Famous Flops
It seems remiss to talk about hyped-but-failed IPOs and not include Vonage (NYSE:VG). Although Vonage is a going concern today, the company's $531 million IPO in May of 2006 was virtually a disaster - the stock fell 24% in its first two days and problems with the offering led to a class-action suit. Although Vonage flirted with bankruptcy, the company is still a going concern and generating actual operating cash flow.

Other names may also ring a bell or elicit a groan from investors with long memories. Genuity spun out as part of the Verizon (NYSE:VZ) and GTE merger. The company IPO'ed in June of 2000, and raised $1.9 billion. That was not nearly enough, though, as the company defaulted on its loans, went bankrupt in November of 2002 and was brought out of bankruptcy by Level 3 (Nasdaq:LVLT). Proving that a good pedigree only goes so far, AMD (NYSE:AMD) spin-out Spansion (NYSE:CODE) managed to elbow Intel aside in the NOR flash market, but could not do so profitably. The company IPO'ed in December of 2005 and raised $506 million - only to go bankrupt in March of 2009 and reemerge in May of 2010.

What Is Old Will Be New Again
If there are relatively few famous IPO flops-to-be out in the market, that is most likely simply a byproduct of the stagnant IPO market. After all, it is the nature of the beast for some of these companies to flop; venture capitalists and company insiders want a quick cash-out, bankers want a payday and investors want to be invested in the next "new new" thing. All of that is a recipe for the periodic disaster, particularly when investors are more interested in getting into the action than buying a piece of a great business. So it really is not a question of whether there will be another big flop, only a question of when it will come and whether enough investors spot it in time to preserve their capital or avoid the mess entirely. (For more, see our IPOs Explained Video.)

Find out what happened in financial news this week. Read Water Cooler Finance: Steady Stocks, Big G's And Madoff News.

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