There are movies that you can keep coming back to… those are usually called “favourites”. 
Anyway, like I said before, I’m just trying to challenge people’s ideas. Comedy is about letting loose, laughing at yourself and others. We can laugh at inappropriate things. Leisure Suit Larry is a comedy. Airplane! is a comedy. Both have offensive material, not to reinforce stereotypes, but to poke fun at the absurdity of taking it too far.
My favourite comedy is actually Bubble Boy with Jake Gyllenhaal. There’s a scene where Jake’s character escapes from his home and his whipped father concocts a fake ransom note to get the authorities involved. His wife reads back the note to him aloud…
“Dear Mr. and Mrs. Livingston, we have kidnapped your son. Give $100,000 dollars or he dies. Signed, the Jews.”
(She looks upon him with disgust and shock.)
Are you kidding? ARE YOU KIDDING? Who in their right mind is going to believe this note Morton?!
THEY’RE THE JEWS. THEY’RE GOING TO WANT MORE THAN $100,000!
Again, that’s funny for obvious reasons and has very little to do with relishing the idea that Jewish people are money oriented or gleefully hating Jews. So when I read people’s opinions about hating comedic stereotype content, I wonder if they honestly got the actual joke.
@Giger_Kitty I remember playing Leisure Suit Larry games and it was always the world conspiring against Larry. In the scene you linked to, Larry clearly likes “the women” so this scene was about him, yet again, not getting the action he’s been so desperately after. If you found that the scene was about making fun of transpeople, I think you missed the joke. Not saying the joke was comedy gold, but it was a joke. Shablee’s character was not persecuted or dragged through the mud. Larry spitting is just his overreaction. I really don’t understand the objection to it. If I were to rewrite that scene, just before the “reveal moment”, I’d have Shablee’s voice go 4 octaves lower though (full on Barry White). 
I never really liked The Mask, but you’ve redeemed yourself many, many times over with your other movie recommendations. The Princess Bride is one of my absolute favourites! I have a soft spot for The Master of Disguise so I’m not impervious to bad taste either. 
Another fantastic comedy is The Bird Cage. Nathan Lane is absolutely adorable and ridiculous. Hank Azaria, as “the houseboy”, is perfectly over the top. On the surface, these caricatures are offensive because they lean on stereotypes. The stereotype invites a viewer’s attention, creates expectations (necessary for a joke and also the foundation of a stereotype), and then the humour can breathe.
I think that’s why I don’t find a lot of well crafted humour in more recent movies because they don’t lean on stereotypes or poke fun at relatable notions. The jokes land flat because there is no proper setup. You have to be a bit risky to deliver good humour. You also need to be relaxed to get a joke. Maybe a lot of people are too uptight these days.
Maybe a lot of script writers are too.