At the 2000 Memphis game in the absolute oven of the Liberty Bowl, an incredibly drunk Memphis fan behind us who was a huuuuuge jackass (cussing at kids, embarrassing every Tiger fan around us, etc. etc.) had smuggled in a bunch of beer. You could bring in coolers and water to the game. Somehow he managed to pull one over on the Liberty Bowl staff.
My other favorite beer-smuggling story: back when Ole Miss played Arkansas (I think) in Jackson, my Boy Scout troop were ushers. An Ole Miss fan comes in with a 4' by 6' Confederate flag, with what had to be 12 Coors Lights rolled up in the middle next to the pole (genius!). One was poking out the top, and my scoutmaster helpfully told him "one of your silver bullets is about to come out of the chamber."