Jokes that don't work anymore (on a contemporary, younger crowd)

It was cooler outside the city, especially before air conditioning was common. People who could afford it sent Mom and the kids to their beach house, their cabin in the mountains or to a resort in the Catskills while Dad stayed in the city and worked all week, joing the rest of the family on Friday nights. It wasn’t exclusively a Jewish thing - but there were always Jewish resorts and non-Jewish ones and few people crossed over. Jewish families didn’t stay at the Italian or Irsih resorts because they wanted a kosher diet - and non-Jews generally didn’t stay at the Jewish resorts because they didn’t want a kosher diet.

Do they still do it? The beach house or mountain cabins, yes . But that type of resort in the Catskills no longer really exists.

The Wisconsin equivalent was (still is, in part) going “upnort” (up north) to either your family’s (or friends’) cabin up on a lake, or to a resort, either in Door County or in the Wisconsin north woods.

A shame because it means I can’t ever use a joke I wrote because those darn “kidz these dayz” wouldn’t know the reference.

“I just flew in from New York… and boy, is that joke tired.”

The whole flashback sequence in the bar where Ted and Elaine first meet, which is a parody of Saturday Night Fever, would likely be lost on younger people today,

Chuck Norris jokes leaving the stage in 3… 2…1…

Timeless? YGBSM. Writing a letter home? Calling your parents “Mother” & “Father”?

The larger theme: “Im scared, this is awful, gee, now I’m having massive fun!” is, as you say, eternal. IMO all of the bits from which Sherman assembles that theme are inaccessibly ancient, and/or NYC upper-class Jewish specific.

No youngster would get the joke I made up in the 1990s, after a famous boxing bout:

What kind of drink should you never offer Leon Spinks?
Aperitif.

No, Polack jokes became huge in the mid-1960s. My dad brought home a paperback book of “Polack” jokes called “It’s Fun to be Polack” published in 1965, many years before All in the Family (1971).

Disaster jokes, being in poor taste to begin with, always have an extremely short shelf life.

(After the Challenger explosion)
What does NASA stand for?
Need Another Seven Astronauts

Much of the Loony Tunes humor is missed by people under 80. And in the writings of Lewis Carroll by people under 140 (and not English).

You’re wrong, though. In the US, window glazing is what you’d assume is caulking. I have no idea why we do it that way, but we do.

How did they know Christa McAuliffe had dandruff?
They found her Head & Shoulders on the beach.

Somewhat similarly:

Why didn’t Natalie Wood shower on the boat?

She preferred to wash up on shore.

Q: How did Jessica Savitch die?

A: Trying to interview Natalie Wood.

Jessica Savitch was a well-known TV newswoman who drowned when the car she was in went into a canal, not long after actress Natalie Wood drowned falling off a boat.

Q: What do you call a Polish guy wearing a $600 hat?

A: Your Holiness.

Q: What kind of wood doesn’t float?

A: Natalie Wood.

Non-Clevelanders might not get this one anyway, but, “What did the Pope and Bernie Kosar tell Art Modell?” “Kiss my ring”.

(Bernie Kosar was the quarterback for the Browns for many years, and of course we never won a Superbowl. Then Art Modell, the owner, moved the team to Baltimore and renamed them the Ravens, and at about the same time, Kosar transferred to… some other team I can’t remember, that then immediately won the Superbowl).

The Cowboys, in 1993.

Also, TIL that yes, white-out still gets used, by people who are still doing handwritten work. OTOH, I think the joke would probably still be lost on younger people, as white-out’s use to correct typing errors is archaic.

The one I remember - I don’t recall exactly how it went - involved Jackson and Pryor being spokesmen for the Ignited Negro College Fund, whose motto is “the mind is a terrible thing to baste.” Would the UNCF and its old motto be recognized by youngsters today?