The most I've ever paid for any event was the past two Voodoo Fests in New Orleans. In '07, I paid $350 for VIP passes which gave me free drinks at a VIP bar so no lines, private restrooms with running water so no porta-johns and REEDICKULUSS lines!!! I got to see Social Distortion, Shooter Jennings, Ozomatli, Red Hot Chili Peppers, Flaming Lips, and about a dozen other bands (total of like 60 bands performed I think).
Last year's Voodoo Fest I just paid $85 for gen. admission and got to see Rage Against the Machine, Smashing Pumpkins and Ben Harper. They had over 110 bands last year.
A festival event like that is the only way I will pay over $100 for ANY show, regardless of who's playing.