As a kid it was totally cool to spend hours and hours playing video games, but now that you're on your own that time must go towards an endeavor that'll make you money -- like playing video games! For the next level of gaming for cash, BringIt.com.
Hatched by a J.D.-toting Chi guy and built by some PartyPoker architects, BringIt lets users lay serious cash ($1 to $100,000) across four platforms (Xbox 360, PS2, PS3, Wii) and dozens of titles like Madden, Call of Duty 4, NBA Live, Mario Kart, and Halo 3; as it involves "games of skill", it's legal in 41 states, including Illinois (guess it's back to playing badminton, Delaware). Registration's free, and opponents can be found via four options: peruse the lobby chat-style "Bark Box", scour "Open Challenges", "Start Your Own Challenge", or get in on NCAA bracket-esque "Multiplayer Tournaments" and hope you're more "Davidson '08" than "Davidson Those Other Years". To save you from yourself, BringIt caps wagering for your first 30 games (games 1-10=$50, 11-20=$100, 21-30=$250), and every user has a "transparent profile" listing rank/games played/results, so the savant from The Wizard can't masquerade as a no-talent hack/Fred Savage.
At month's end BringIt will implement a smack-talk-enabled, user-to-user IM/Skype service, and they've recently added a widget that'll send you a text message whenever someone challenges you/accepts your challenge -- so you'll know just when to bust out of that salary negotiation, and get down to something serious.