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1.
The word failfest is a compound word composed of 2 words fail and festival(fest). Fail is comonly used to let someone know that they suck at something or they got pwned. A festival is a celebration or gathering of some sort. So a failfest is a gathering or celebration where people that fail go.
As Johnny walked with his friends to school he tripped and fell on his face. His friends said " Lol Johnny should go to failfest for that, what a noob."
by ProMaster April 19, 2009
 
2.
1. When a group of people who are really terrible at something gt together to do that exact activity, peope who cannot play guitar hero or rockband on the expert setting, yet get together and hold a tournament, people who have extremely slow cars and get together at the local reacetrack to run over 14 second quartermile times, any art galleries for preschoolers or metally handicapped people.

2. when a single individual goes on an unfortunate series of events in wich none of them go the way he or she intended, among these series of events one instance of falling down in a matter that lacks any notion of grace is required, usually said individual ends up humiliating themselves publicly on an epic scale.
Friend: what happend last night, its like i got hit by the bad karma bus

Me: I dont know but that was the greatest failfest ive ever seen.
by sonofturbo October 07, 2009