6. The Dragonborn (The Elder Scrolls: Skyrim)
When you're challenged to a drinking contest in Skyrim, it doesn't seem like it should be a problem - you're the Dragonborn! You can go from new student to Head Principal/Dean/Dumbledore of the College of Winterhold in about 3 days, you eat raw meat with disturbing regularity, you suck down dragon's SOULS without any problems...so how bad could 3 drinks be? Pretty bad, it turns out.
After accepting a drinking challenge from Sam Guevenne, you wake up in a temple you apparently totally trashed the previous night. During your inebriated blackout, you did some gross stuff at that temple, sold someone's goat, and got engaged to a hagraven, who you then have to murder to get back the wedding ring. Oops. Not very becoming of the savior of the realm. At least you didn't get into any bachelor party hijinx with Zach Galifianakis.
5. Jason Brody & Friends (Far Cry 3)
All Jason Brody and his pals wanted to do was have a booze-soaked, relaxing vacation in some nondescript Pacific islands. They just wanted to live an IRL version of that the beginning part of every horror movie and skip the part that always follows the partying, drinking, and debauchery. But within minutes of beginning Far Cry 3, your drunken escapades have gotten you captured by a group of psychotic mercenaries, led by insanity-definer Vaas, who proceeds to kill a few of your bros as you sober up and try to figure out a way off the island. Here's a tip: if you're gonna go on a drunk-cation, try to do it away from tribal islands swarming with mercenaries, wild tigers, and magic tattoos.