The discussion below about Network reminds me of the other movie starring William Holden about the entertainment media and generational differences, Sunset Boulevard.
The main influence on the zeitgeist is the trend in the violence rate, and by 1950 when the movie was made, it had been falling ever since the 1933 peak. Our most recent peak was 1992, so we're just about where things were when the original was made, 15-20 years into falling-crime times. Since similar environments produce similar outcomes, we should be able to make something along the lines of Sunset Boulevard by now.
No one ever knows how well a movie will turn out beforehand, but it would be worth a shot -- and it would certainly set a higher bar for remakes than all other recent attempts. Perhaps all involved would take the project more seriously than the failed resurrection of Conan the Barbarian.
By 1950, the pictures really had gotten small compared to the Roaring Twenties. It didn't have to do with the shift from silent to talkie movies, though, as the talkies from the early '30s are still big productions, exotic, sublime, ornamental, etc. *
At first, people who lived through the meaningful and exciting times might have thought that the move away from it was just a brief fad. After 15-20 years of steady erosion, though, it becomes hard to ignore. So we can take stock of what the movie culture was like during the recent heyday of the later '70s and '80s, and how sharp the change has been to today.
Gloria Swanson was born in 1899, growing up entirely during rising-crime times, and becoming a star during her 20s when the homicide rate was nearing its ceiling. For the recent cycle, that would be someone born circa 1958 who became a star in the '80s. Really, Kathleen Turner is about the only one who could bring Norma Desmond to life today.
William Holden was born in 1918, so his counterpart would be born in the late '70s, and doesn't have to be a superstar right now but at least has leading man potential. Why not Leonardo DiCaprio? It's hard to think of anyone from the later Gen X-ers or Gen Y-ers who can act well. He could play independent and ambitious while also lapsing into passive and disaffected.
I don't think the age of Norma Desmond's ex-husband-director-butler is so important, since he doesn't play a role in the inter-generational dynamics. He just has to have been famous during the visual-action days, and faded from public recognition during the chatty-introspective days. There are probably lots more choices here. One who comes to mind is Richard Donner, who directed The Omen, the first two Superman movies (the good ones), the Lethal Weapon movies, and The Goonies, but who hasn't done a whole lot during falling-crime times.
The actress who played Betty was born in 1928, an early Silent Gen girl, so her descendant today would be a Millennial born in the late '80s. She doesn't have much character development and is there mostly to serve as a stable, wholesome foil to the breaking-down Desmond character. So she doesn't have to be a very good actress. I avoid most new movies, so I have no ideas here.
Like the original, the remake should avoid any nerdy focus on the technological change, and stick to the sweeping changes in the whole zeitgeist. At most, maybe Donner and Turner, who are used to the world of demanding physical stunts and dazzling visual effects, could be shown having to get by in the new world of ugly CGI and boring stunt work. DiCaprio as Joe could be shown trying to bring his scripts to risk-averse studio suits who only want to make Harry Potter 29 and Hungry Hungry Hippos: Origins.
Also as with the original, it will be hard to keep it from being one big slam against a bygone era. But even little details showing how much more magical it felt back then would humanize the older characters -- they're trying to get by in a world that doesn't want to believe in magic anymore. The shots of Norma Desmond's image-oriented silent films, the grand interiors of her palazzo, and the intimate style of dancing all contrasted with what the average movie-goer would have been used to in 1950.
The remake could show how much more spectacular real exotic footage is, to remind audiences who've grown used to or only known what CGI jungles look like. Turner's home could be in the Art Deco revival style, to contrast with the beige / olive / black minimalism of today. And she and DiCaprio could slow dance to just about anything from the good old days -- "Take My Breath Away" would be laying it on thick, but then maybe Turner's character is desperate enough to try to take it over the top like that. Just something to play against the isolated "dancing" of the younger generation.
As for who would make it? The team at Mad Men have done a great job reviving the mid-century for contemporary audiences, and not just in Pomona. They are in TV rather than movies, but it still seems like they'd make a good core. No ideas about who should direct it. I don't think the Coen brothers could keep the characters' tone straight and deadpan; there's always something self-aware and cartoony about their characters. Maybe the Mad Men people could keep them in check, though.
* Probably the last great example of Jazz Age movie-making was King Kong, released in 1933 at the peak year of the homicide rate. The entire visual culture went limp after that, so that cinema-specific causes don't really capture what changed. Look what happened to architecture, design, and museum art, for example -- the public turned its back on Art Deco and Expressionism, preferring instead the minimalist cocoons of International Style buildings and the emotionless, unrecognizable abstract art of the mid-century.
Once crime rates began soaring during the '60s, '70s, and '80s, visually oriented movies rose from the grave, slowly at first but taking off in the later '70s. Again that drive took over the entire visual culture, including the return to colorful, figurative painting, psychedelic posters a la Art Nouveau, the Art Deco revival, and so on. As the crime rate has fallen since the '90s, the visual appeal of most movies has disappeared to what it was like during the average mid-century movie.