As of late, Hollywood has had a fascination with (IMO)needlessly remaking some classic and not-so classic films.
People frequently say this - but it is not at all a new trend. Hollywood has almost never been about original material, canabalizing freely from itself, plays, books, comics, video games, amusement park rides - basically anything. The classic 1939 Wizard of Oz starring Judy Garland was the 4th film adaptation of the book. Remakes have been happening basically since someone first turned on a camera.
The thing is, people who try to remake shows like these miss the point as to why they're considered cult favorites. They were all about the actors who played the characters, not so much the characters or the storylines. You could remake Citizen Kane line by line and it would fail because you didn't cast Orson Welles. Casablanca's story is penny ante B-movie stuff that was cobbled together on the fly, loosely based on a failed stage play; the movie worked because of Bogart, Bergman and Claude Rains. Try to do a version without them, and it'll suck. David Soul (yes, of Starsky and Hutch fame) found that out when he tried to do a TV series remake in the 80s. And Timothy Dalton was almost laughed out of the room when he stepped into Clark Gable's shoes as the new Rhett Butler in the Scarlett mini-series, perhaps not realizing that Rhett Butler was just a cipher and the appeal was in Gable, full stop.
Interesting point and I think you are quite correct - but then most films are about hitting the right chemistry between material and cast. I was the first to say when the teasers for Pirates of the Carribbean were running around - Seriously? They're down to spinning movies off Disneyland rides now?? But the chemistry and material was a near-perfect mix, turning into a funny oddball blockbuster.
So, as you point out about
Get Smart - find a new "right mix" and just about anything can be remade successfully. I think you may have a point that a few pieces are so iconic though that it would be hard to overlay the image of them that exists in our minds with any new cast. Occasionally though, they can be cannibalized too. I remember seeing the Siskel and Ebert review of the so-bad-it's-good comic book adaptation
Barb Wire which ripped off Casablanca without shame. Both critics agreed it was so outrageous that it worked.
As for
Gone With the Wind, I have longed for a new adaptation of the book, because the 1939 version was fairly sanitized, leaving out some of the best stuff from the book, including two of Scarlett's children!! Sadly, political correctness precludes any new version of this classic, but absolutely racist, tale ever hitting the screens again.