Mudd's Bastard (TV14)
Stanton Rothschilde Mudd (Norm Macdonald), the son of Harcourt Fenton Mudd, is caught smuggling sentient sex slave animals from Orion to New Jersey, but all is not as it seems. Did the elusive Mudd want to get caught, and what is the connection to his father's own history of selling slaves in the Federation?
This show had so many amazing moments, but I think my absolute favourite was when he was first extolling the virtues of the Man-Grate. Ostensibly, all he was doing was explaining the great features of the Man-Grate, but it was somehow the most subversive and hilarious thing ever.