It only happens once every four years, and the event doesn't get enough attention. No, I'm not talking about presidential elections, the Olympics, or Billy Crystal hosting the Oscars.

I'm talking about Leap Day -- that special occasion that can (technically) enable a person to get his or her license by age 4, a college degree by age 6, and fade into retirement at around 18 years old. In honor of this rare day, Fool analysts are going to be "taking a leap" on some stocks that many may consider foolish (small "f") and risky.

Been there, done that
Without a doubt, swimming against the current has its benefits. Consider back in early 2009,when Fool analyst Rick Munarriz asked readers when Sirius XM (Nasdaq: SIRI) would file for bankruptcy. At the time, rumors were swirling that the announcement was only days away, yet Rick had this response:

I'll tell you my answer. You'll laugh. I'll explain. You'll probably keep laughing. In short, I don't see Sirius XM filing for bankruptcy protection this year.

Rick was definitely taking a leap on Sirius; in fact, most of the commenters for the story simply offered up the date of future bankruptcy. But those who bought Sirius back then have seen their investment multiply 20-fold.

Nor was it Rick's first such call. Back in February 2007, he defended Chinese search engine Baidu (Nasdaq: BIDU) after the company issued lower-than-expected guidance. The stock sank 9%, and it had a one-star rating -- the lowest-possible -- in CAPS. But Rick argued: "The market's got Baidu all wrong here." Since then, the stock's up almost 1,200%.

Look before you leap?
Now, this doesn't mean Fool analysts always look for stocks that are on the verge of bankruptcy, hoping for a miraculous recovery that could one day offer up Sirius-esque returns. Nor is every stock that misses guidance a smart buy. No, Fools may be an irreverent bunch, but there's a method to their madness.

Instead, Fool analysts have picked a motley collection of stocks that, for one reason or another, seem to be unloved. These companies may be risky (or boring), but they also have enormous upside potential.

Are you ready to take the leap?
Now, not all of the stocks you'll see in this series will bring results like this. Having a diversified portfolio that you're comfortable with is the most important thing.

But if you're ready to set aside a little money and swing for the fences, click on the links below to see what stocks these analysts are taking a leap on.