The most important lesson any man learns in college is that gambling on sports is awesome, so it's only natural that a bunch of college students would come up with a legal way for you to keep doing it well into your 90s. Bet your ass off, at CentSports.com
Started by a group variously affiliated with Texas A&M, Cent puts advertising dollars into user accounts, thereby circumventing the UIGEA's motherly ban on accepting players' cash money, and allowing you to place all manner of bets (parlay, over/under, whatever) on most major college and pro sports. The deal: upon signing up, you're credited with ten cents, which sounds like an insulting play-money situation, but can potentially turn into real earnings, with the highest cash-out to date exceeding $1000 -- enough for a trip to Vegas to lose money the old fashioned way. Once you've made your picks, you're presented an option to increase your wager's value by 50-100% by watching an ad; if your account drys out, you're credited another ten cents, and you start all over again -- in other words, you can't lose money, but those titillating promises made by Progressive Auto Insurance will be tattooed on your brain forever.
In another novel move, Cent's buddy list feature lets you check out what bets your friends are laying, allowing you to soak up their wisdom, and haze them mercilessly for forgetting the second-most important collegiate lesson, never bet on the Aggies.