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21 Dumbest Moments in Business - 2008

Last Updated: December 29, 2008: 9:04 AM ET

(Fortune) -- We don't know whether to laugh or cry. Our annual list of the year's most laughable moves proves that, even in moments of crisis, stupidity lives on. See the full gallery.

1) Detroit execs flying to D.C.: The chief executives of General Motors (GM, Fortune 500), Chrysler and Ford spark outrage when they fly their corporate jets to Washington D.C. to beg Congress for a multi-billion dollar bailout. More

2) Detroit execs driving to D.C.: Given a second chance after the private-jet fiasco to plead their case before Congress, the Detroit 3 take to the road. More

3) Henry Paulson's initial $700 bailout proposal: All of three pages, the Treasury Secretary seeks carte-blanche access to government funding with scant details on how or where the money will be spent. More

4) The final bailout: When Congress is done with it, the measure balloons to 451 pages and is loaded with pork barrel spending - including, unbelievably, a cut in taxes on toy arrows and an extended tax break on "wool products." More

5) The Mozilo e-mail: The now former Countrywide CEO mistakenly broadcasts his thoughts on a customer's plea for help with a home loan. More

6) The iPhone 'I am rich' app: Eight people download a $999.99 screen-saver for Apple's (AAPL, Fortune 500) iPhone. More

7) Paulson's 'bazooka': The Treasury Secretary tells Congress in July he thinks he won't actually need to use the funds he's requesting to support Fannie Mae and Freddie Mac. More

8) Tough talk from Fannie Mae: In May, CEO Daniel Mudd says his company will "feast" on weakened competition in the mortgage market. More

9) Scandal at the Department of Interior: The agency's Inspector General finds that staffers were taking gifts, having sex and engaging in illegal drug use with employees of some of the oil companies they oversee. More

10) GM's Lutz on global warming: The General Motors exec behind the Chevrolet Volt electric car hands environmentalists another twig to beat GM with when he reportedly calls global warming "a crock of sh-t." More

11) Hope for Homeowners - er, not really: Congress passes bill to keep hundreds of thousands of troubled borrowers in their homes. A whopping 321 applications get filed. More

12) Ban the short-sellers: To head off a market onslaught, the SEC outlaws short-selling on 799 financial stocks. Remarkably, investors find other ways to punish the group and the sector sinks another 25 percent. More

13) McCain on economics: On the morning of Sept. 15, as Lehman Brothers declares bankruptcy, Republican presidential candidate John McCain declares "the fundamentals of this economy are strong." More

14) Obama's tough talk on Nafta: A top economic adviser privately assures Canadian officials in February that his candidate didn't really mean it when he threatened to renegotiate the North American Free Trade Agreement. More

15) Microsoft bids for Yahoo: The $31-per-share offer represents a 61% premium over Yahoo's (YHOO, Fortune 500) price at the time of the February overture. More

16) Yahoo turns down Microsoft's offer: If Microsoft's (MSFT, Fortune 500) offer for Yahoo was wrong-headed, Yahoo's opposition to it was downright bone-headed. More

17) The Madoff miss: As news reports reveal that the Securities and Exchange Commission had probed Madoff and his New York City investment firm over the years, chief Christopher Cox cops to the embarrassing screw-up. More

18) Oil speculator scapegoats: Are speculators to blame for $37 oil too? More

19) Steve Jobs' obit: In August, Bloomberg News accidentally releases an obit for Apple CEO Steve Jobs, who - despite a well-publicized brush with pancreatic cancer - is still alive and kicking. More

20) Phil Gramm and the "nation of whiners": In early July, as the financial crisis spreads to Main Street, McCain campaign co-chair and former senator Phil Gramm appeals to voters and their economic anxieties by calling them a "nation of whiners" and dismisses a troubled economy as a "mental recession." More

21) Bill Miller comes up short: The fund manager's contrarian bets on Bear Stearns, AIG and Freddie Mac cost his investors plenty. More

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