I've sung at Otakon before
I ended up singing Anime Janai from Gundam ZZ (double zeta) but really that's all I've ever sang... and I actually practiced and memorized the lyrics and a loose translation of what they mean so that I wouldn't sound like a complete idiot... Unfortunately it's rather annoying having to wait for your turn seeing as how everyone else who goes up sing the songs from the same animes over and over (how many times do you hear anything outside of FMA, Inuyasha, Naruto, and Bleach anyway?)
It's still fun though