Well we had a Picard imposter sing Hearts of Oak. Although if we really wanted it authentic, he'd sing it in French (yes there are French lyrics to Hearts of Oak).
Sisko: Who's the Starfleet Cap, that punches out Q to shut his trap? SISKO!
Quark: Smooth Criminal
Gul Madred: Blinding Lights
Beckett Mariner: The Touch (with Transformers dialogue!)
Not sure. It's pretty obscure, I think I was able to get it to run on my old Windows Vista laptop. No such luck in the Win 7 era though.