Although not eligible, since they were only guests on an episode of Star Trek, no one would beat the Space Hippies.
Fuckin’ Space Hippies, maaaaannnnn!
I can’t find a specific clip of what’s next, but next Spock makes like a Final Frontier version of John Sebastian and jams with a hippie chick on a space autoharp.
Here’s Captain Kirk keeping it gay!
Here’s Uhuru singing AND playing an intergalactic lute!
Take that, Sting!
This time it’s Spock accompanied by the intergalactic lute—played by the little guy from Wild Wild West no less!