South Park

If it’s someone who has been hesitant because, “it’s offensive” then Stunning and Brave should be included

I think that if you are showing to a specific person an episode about something that they relate to may work better. I showed Freemium isn't Free to a friend who is addicted to gacha games and has an alcoholic friend and she loved it.
In general tho, Butterballs, Scott Tenorman Must Die, Woodland Critter Christmas could be my pick.

emotional touch: the city part of town bc kenny saved up enough to buy his little sister a doll (it always gets me)

scott tenorman, fat butt and pancake head, casa bonita are obviously classic.

Scott Tenorman Must Die, How to eat with your butt, Fat Butt and pancake head

Mr. Jefferson

Scott Tenorman Must Die, ManBearPig, Good Times With Weapons

Scott tenorman must die is a must.

Good times with weapons Casabonita Le petit tourette All about the mormons Cartmanland Cartman joins nambla Trapped in the closet

So many good ones to chose from

gay badge of gayness, scott tenorman must die, & fishsticks

Scott Tenorman Must Die, Good Times With Weapons, Make Love, Not Warcraft.

if a celebrity they like or hate is on south park, show them that episode.

Casa Bonita, Vindaloop (I don’t remember the full name), and the Scientology episode. I feel like the combo shows the range of the show and also a bit of an in-depth look at what the show can get into without going dark and deep fast.

The black friday trilogy

the one with Cesar Milan I used on a friend of mine and he was hooked.