>Some things don't need updated graphics?

I think the underlying theme of the article is the game was an organic whole. It wasn't just a good idea they put together in the technology available at the time, it was of the time. The best example is:

"once they started looking like actual pin-up girls, that dimension of the humor was lost. It gradually felt less like a joke about a guy who wants to hook up with sexy ladies and more a vehicle for actually looking at sexy ladies."

the improved graphics and the point-and-click interface completely change what the thing is. It stops being some wink-wink "You're playing video games because you can't find a date but we're such losers we had time to make a game for you" and something commercial and knowing. If you knew about any of the Sierra titles you were almost part of a family. You could write to the people there or at Infocom or wherever and reasonably expect a response. Now video games are an industry and every possible niche is filled to bursting.

Then again, there's always some indie game or single-A title that drags me back.

It ties into context, I think. This game is funny because it subverts the expectations of the adventure game genre. Improving the graphics weakens this association.

Worth pointing out that, regardless of the context, comedy rarely ages well. For example, if you watch popular standup comedy routines from the past, they're often unfunny, even when performed by comedy legends.

I love the Marx Brothers, both the slapstick and the double entendres and asides and retorts. Their amazing foils in their straight-men and women helped make their comedy timeless imo.

One obvious exception is physical comedy. Buster Keaton is timeless, and in just one Three Stooges short, the contrast in how physical and other kinds of comedy age is apparent.

Agreed: I watched Singin' in the Rain recently. Donald O'Connor's physical comedy is really the standout element in that movie.

There's a special on Netflix right now where Jerry Seinfeld goes back to roots and repeats (one of) his first standup routines.

I found it fantastic, but a friend hated it. We both were very perplexed by the other's perspective.

Anyway, worth a watch! Or you'll hate it!

Oddly, I find them funnier--times change, tastes change.

Perhaps since standup comedy particularly relies on edginess and cultural context, as opposed to some other mediums?

Certainly. Undertale is a perfect example. Better graphics would kill it.