Sometimes I think that one of the words that we’ll always remember from 2008 will be bailout. (Actually, it was Merriam-Webster’s Word of the Year for 2008, so I’m not too far off here.) I mean, every time you turned around it seemed like someone or some company was getting a bailout. There were the banks, then the automakers wanted in on the deal. There was a kind of housing bailout. And then others got in on the idea.

My friend Jen Singer posted a funny video asking for a Halloween bailout from the candy makers. I mean, if the government was going to buy up $700 million worth of bad investments, why should’t moms like Jen ask M&M/Mars and other candy companies to help her when it came time to purchase Halloween candy?

Soon enough bloggers started asking for tongue-in-cheek Christmas bailouts, and I’m wondering if the trend will keep going into 2009–with requests for a Valentine’s Day bailout (maybe I could hit up the candy makers that Jen did?) or a back-to-school bailout?

All satire aside I just found out about a contest that you can enter to get a bona fide bailout from your credit cards, mortgage holder and other creditors. Overstock.com launched the 2009 Monthly Family Bailout Sweepstakes in order to give those who visit Overstock.com the chance to pay their mortgage, credit cards, or other large debts in a troubled economic time.

According to an Overstock.com press release, the $10,000 award will be directly paid to the winner’s designated creditors, and includes an additional amount designed to cover any taxes that may apply. Each month Overstock.com will announce a new winner of the $10,000 prize.

The cool thing is that while you’ll be automatically entered into the bailout sweepstakes when you shop on the website, you can also just enter your name to become a part of the sweepstakes, which is great if you’re not interested in spending cash right now but wouldn’t mind taking home some extra bucks.

I’ve been a shopping fan of Overstock.com for quite some time now–they have great deals on high thread-count sheets–and I love the site’s $2.95 flat shipping rate, which is very reasonable in this day and age (though, of course, free shipping is better).

Good luck if you decide to enter the bailout contest. Also, if you’ve heard of any other tongue-in-cheek bailout programs or promotions, let me know what they are.