The transition started earlier, just think of "The Bottle Deposit" in Season 7 (the last season Larry David was showrunner), which could be entirely a Simpsons

The transition started earlier, just think of "The Bottle Deposit" in Season 7 (the last season Larry David was showrunner), which could be entirely a Simpsons episode with Homer and Barney instead of Kramer and Newman. IMHO, the combination of silliness and darkness in "The Invitations" (also Season 7) is also very much comparable to "Homer's Enemy", although the Seinfeld episode is much darker.