Generally, political humor doesn’t age well because the politics and politicians of one generation are mostly irrelevant and unknown to future generations.
Worse still is humor that tries too hard to be hip (and I suppose people who use the term, “hip” like I still do, aren’t exactly “cool”…but I digress). Case in point: Rowan & Martin’s Laugh-In. I was luke warm to Laugh-In’s humor during its original run, but watching it now is cringe-worthy.
To me, the humor that connects most timelessly, generation after generation is that of the Big-3 Silent era comics: Chaplin, Keaton, and my personal favorite, Harold Lloyd. These comics (and their writers and directors) crafted humor to a very high degree and I laugh at their films today as intensely as I’m sure their contemporary audiences did.
Likewise, the screwball humor of Hollywood’s Golden Era still make me bust a gut. I’ve recently we-watched depression-era classics like, His Girl Friday, My Man Godfry, It Happened One Night, The Awful Truth and Bringing Up Baby. These dialogue-driven films are funny, no matter what generation you’re from. And, the actors of these flicks delivered their lines with spot-on elocution, so you’re not likely to miss any gags. Case-in-point, His Girl Friday dialogue clocks in at 240 words per minute (compared to average movie dialogue of 90 words/minute) and each word is clear, concise and side-splitting funny. I love Cary Grant’s and Kate Hepburn’s mid-Atlantic accents!
I still chuckle at the 3-Stooges and more-so, the Marx Brothers; Martin & Lewis and Abbott & Costello, not-so much.
Sid Caesar’s Show of Shows (with Imogene Coca, Carl Reiner and Howie Morris): still damned funny.
Richard Pryor, George Carlin, Gilda Radner and Gene Wilder: also still damned funny!