Out of 100 episodes, I probably enjoyed about 25 watching the series now that I'm older. The reason I'm rewatching the series is because my brother is now watching it, and I see now that the humor was just so juvenile. In contrast, a lot of the humor is inappropriate sexual innuendo to appeal to parents. The stereotypes are horrible, with the smart Indian kid, sassy black girl, dumb blonde girl, gross white boy, and the two adults who get no respect. Also, Jessie's dialogue is so cringey. They seem to put a laugh track every time one of the kids highlights one of the flaws in the adults (like how Jessie is lonely). They make some shitty joke about a serious topic and slap a laugh track. Example:
Kid: You're lonely and a loser and you can't get a boyfriend
LAUGH TRACK
Jessie: I'm gonna go cry now
LAUGH TRACK
Kid: You're lonely and a loser and you can't get a boyfriend
LAUGH TRACK
Jessie: I'm gonna go cry now
LAUGH TRACK