TOS: "The Enemy Within" (s1e5)
KIRK'S TOXIC MASCULINITY is unleashed after a transporter accident involving mystery ore from a freezing planet splits him into his Negative Side and Positive Side. This mascara'd drunk sexually assaults Yeoman Rand. Meanwhile, the Positive Side winds up being the passive side and his inaction and softness begins to offend Mr. Spock!
It's an episode that only could've been written in the 1960s and it should come as no surprise that its general statement about the darkness inside every man comes from a Twlight Zone writer -- it's a very Twlight Zone message. For your consideration: Bryan and Kristen play Trek Marry Kill with it and see if the episode holds up despite sexual assault, a dog in a dragon costume, and an inexplicable storyline where the ship can't send down a shuttle to rescue Sulu & some redshirts!