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[AdriaSterling]

Hi, my girlfriend and I are wanting to do a skit this up-coming June and I am writing it.
What we are wanting to do is actually "preform" a song that our characters do in the show.

What I am curious about is tips on going about doing such a thing, what you've seen so far as rules, and any other things that might be helpful. It would be greatly appreciated.

[CapsuleCorp]

The only rules that matter are the ones at the convention at which you plan to enter. Read them, they should be on the con's website. And if not, email the con staff/cosplay staff/cosplay director, who makes the rules.

Rules differ wildly from con to con. Most cons where I spend my time? Don't allow you to actually sing or deliver any dialogue at all from the stage. It's too complicated and expensive to have microphones on stage and a sound crew who can properly and intelligently manage said microphones, so MOST cons require you to pre-record everything and the only thing you can do on stage is lip sync. But, the only way to know for sure if the con you're planning to perform at also has this rule or if they do things differently, is to read THAT con's rules page. And if they don't answer your questions, email the director.