Bojack Horseman “That’s too much man!”
Not depressing per se but strangely dark - in Seinfeld S4 E9, Crazy Joe Davila, dressed as the clown, beats up a group of muggers.
And very sad, in the Brit comedy Upstart Crow, season 3 finale, when Shakespeare’s son dies.
WKRP in Cincinatti and the Riverfront Coliseum/Stadium stampede. Based on this incident.
Beautifully done.
Yes, they had changed the name of the show the season before. But the episode still happened.
All the Bojack episodes about his parents were depressing as hell.