My freshmen year, the entire hall I lived, we were all friends. We'd all go to dinner and do shit together. We were the tightest group of people in the building including the RA on our floor, he was just another one of the guys.
On the WSU campus at the time there was only one place to eat open after 7, and that was a place called Flick's (fast food with old movie posters and such). So, the RA is was a decent sized guy, his nickname was GC, grilled cheese, named so by his victory in a grilled cheese eating contest.
Anyway, he also ran a local radio show late night, and we'd all call in and provide him with stuff to do, we were probably the only people actually listening at the time. So one night, he starts talking about how he was damn hungry and was talking about how he could eat the entire Flick's menu in one sitting.
Of course, we instantly call him on it and eventually set up this thing called the Flick's challenge. He has to eat one of everything on the dinner/lunch menu (they did serve breakfast too, but we were trying to be reasonable), and we would pay for anything he could eat + 20$. For anything he didn't eat, he would have to pay us the menu price for it.
Now, seeing as it was just a grill, it was basically, fries, curly fries, a couple burgers, chicken sandwich, hot dogs, corndogs, veggie burger, a drink, a salad and a milk shake.
He got through a single burger, the double burger, fries, a shake, the chicken sandwich, a corndog, the salad, and part of the veggie burger. Then he lost it. All over the table. It was not a pretty sight. The place used plastic baskets with a wax paper covering to server the food in, and we filled three of those up by the time he was done puking his guts out. He felt like shit the rest of the night and well into the next day.
To this day, he still owes us for the shit he didn't eat. It comes up in conversation from time to time as a joke now days.