My favorite TV show is a super old animated web series called "Unforgotten Realms". It follows the adventures of a D&D campaign with bits in both real life and the game
The show originated on Newgrounds in 2006 but was actually picked up by The Escapist Magazine where it ran from 2008 to 2009 until its cancellation (along with the cancellation of pretty much everything else on The Escapist)
I was highkey obsessed with this show in highschool, I watched through it in its entirety multiple times. I even have a signed DVD of the first season (with bonus disk!). I've been rewatching it lately and, honestly, it holds up super well and I think shaped my sense of humor in a major way
Now, all of this comes with a big disclaimer; the show uses language and jokes that are absolutely not okay. Some of it is kinda understandable in context (late 2000s internet was al much... edgier place), but some of the jokes really weren't okay at the time. The artist of the show has acknowledged this and recognizes that these sorts of things aren't acceptable anymore.