Congratulations...this is a great story!
I've actually got a story that was both my best and my worst live show as well. About 10 years ago (when I was playing drums) I was in a cover band. We played pretty much anything we could all agree was awesome (so naturally...we only knew like...5 songs).
Anyway...one day we were opening for a local band that was playing at Stubb's (a popular live music joint around here). We were excited as it was our first real 'gig'. We only had time for 2 songs...and we decided on Tom Petty's 'Runnin' Down a Dream',and Korn's cover of 'Word Up'. 2 songs of which are now worlds apart in my rankings of 'awesome songs'.
The weak point of the band was our vocalist. He just didn't have the voice for either song. To make a long(er) story short...it was horrible. Crowd enjoyed it a little (I guess), but it didn't really get anybody going. So...worst gig ever, right? Nope...And here's why. 1: I had a lot of fun even though it was awful. Playing for any size crowd is an amazing feeling. 2: Our vocalist thought the crowd was hype enough at the end of our short set for a stage dive to work...he was wrong. He jumped from a stage about 7 feet up right onto the floor. Dropped from the band the next day with a busted face. Normally I'd have felt bad, but he was a cocky jerk that just got put in his place.
I couldn't stop laughing. Best. Live. Show. Ever.