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!)