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Everything Rob Schieder started in.
None were very well liked even when they were fresh, but things like “Big Stan”, in which his pipsqueak convict character has to go on a karate-kid-style journey to learn martial arts from David Carrodine in order to fend off rapists before he heads off to prison is kind of a case study in a whole genre that could be called ‘damn, you really thought that was funny?’
Norm MacDonald and some of the other SNL folks dabbled in some of the same jokes, but were much more talented, so some of this stuff feels a little forgivable. Schneider though… oof.
Also: I haven’t seen it, but I’m going to guess that 2008’s “You Don’t Mess with the Zohan” – in which Adam Sandler stars as an Israeli Mossad super ninja who wants to be a stylist – probably didn’t age great.
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Don’t mess with Zohan is conceptually wild now. Damn.
he’s the one that hasn’t aged well. gone off the deep end, he has. antivax, transphobe, trumpette, pimps for moms for liberty… you name it. actually got pulled from the stage in Regina (ca) during an event two years ago, in the middle of his routine, due to piss-poor taste and ‘inappropriate’ (to say the least) content. src
It can’t age poorly when it was never good to begin with
It was unwatchable cringe shit when it came out.
I know cause I lived with a dumbass drummer who thought Sandler was funny. Even HE was turning that crap off halfway through.