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If you want to keep happy memories, never rewatch a comedy special older than 10 years. It’s incredible how fast most jokes age.
I think there are some big exceptions. For example- Robin Williams at the Met was an amazing show and is still extremely funny.
Probably true, I usually don’t rewatch anything in video format. It’s kind of a weird quirk of mine.
Some are timeless, I can watch Burns and Allen routines and they are still hilarious. Topical humor is very of-its-time though.