Gunning for that early 2000's Cartoon Network feel, PSG is a stark and unusually crass change of pace from conventional anime. I highly recommend the English dub.
Panty & Stocking with Garterbelt
Ghost Stories (English Dub)
The heckling humor of MST3K meets Abridged Series humor in this hilarious and crass parody of itself where Voice Actors were given free reign.
Anime Crimes Division
Take the humor of ProZD, strictly apply it to anime, add a production crew and cast, and you'll have a good idea of what to expect.
Yakitate!! Japan
Yakitate!! Japan is a goofy, wholesome comedy that channels a similar vibe to the great Abridges series of the early 2010s with quality humor and the cast doesn't really take the show seriously.
Konosuba! The Legend of Crimson
The Konosuba Movie is the series at its absolute best. From start to finish, the comedy is perfectly on point.
Re:Zero – Shorts (Break Time & PETIT)
Good short snacks of web-comic-flavored humor.
Isekai Quartet
The casts of Overlord, Konosuba, Saga of Tanya the Evil, and Re:Zero join in a Smash Bros. flavored crossover to experience...High school in Japan?
KonoSuba: God’s Blessing on This Wonderful World!
The pinnacle of well executed and clever stupid comedy. Strongly channels the vibe of if a group of stupid friends got together to play D&D, and one of those idiots is the DM.
At a Glance Anime 