Working from the bottom up, I'll start with Bringing Up Baby. In the genre of screwball comedies, you just can't beat His Girl Friday (1940). It has the same director (Howard Hawks) as Bringing Up Baby, and Cary Grant is also in this film. It has a much funnier script, and Rosalind Russell's sharp-tongued news reporter is a much more effective comic lead than Katharine Hepburn's quirky heiress. I really don't know why this movie wasn't on the list. It did make #19 on AFI's 100 Years, 100 Laughs list, but why only there is a mystery to me. This is a gender-bent version of the play and movie The Front Page (1931) which is also a good film. The Front Page would be re-made in 1974 with Jack Lemmon and Walter Matthau (which I like even better than the 1931 version), and His Girl Friday was itself updated in 1988 as Switching Channels, which I would recommend avoiding.
Here's another option: Nothing Sacred. This is a very funny black comedy from 1937 that makes me think if the Farrelly Brothers had been around back then, this is a movie they would have made. Dorothy Parker is one of the many uncredited writers who worked on the screenplay, so that should give you an idea of just how biting some of the dialogue is.
Okay, moving on: Easy Rider (1969), as I said, just doesn't do it for me. If we're talking about partly-improvised films that reflect the counter-culture movement of the late 60s, I'd much rather watch Medium Cool from the same year. Mixing fact with fiction, this was shot partly during the 1968 Democratic National Convention and, when the anti-was protests were met with violent reprisal, much of that is incorporated into the latter part of the movie.
Okay, The Deer Hunter is tricky. It was one of the first films of the 1970s to address the war in Vietnam, it just did so with a great deal of "artistic license." I'm going to have to go a little outside the era to 1989 with the second entry in Oliver Stone's trilogy (Platoon was the first). Born on the Fourth of July far more effectively covers the pre-war innocence, the nightmare of battle, and the disenfranchisement and disillusion of soldiers returning home, and, unlike Michael Cimino, the director and screenwriter both actually served in Vietnam. (Not that one has to have been a Vietnam veteran in order to make a good Vietnam film, it just cheeses me off that Cimino misrepresented his own military service to gain publicity for his film.)
For Gone With The Wind, I'm going to focus a little more on the heart of the film, which is about a family's adjustment to a changing way of life amid many personal and financial hardships - with a love story thrown in for good measure. If Gone With the Wind is on the list for its cinematography and scenic design, then there are many films already on the list that did it just as well: The Wizard of Oz from the same year, for example.
I'm going to give you two to choose from here. The first, Mrs. Miniver (1942), looks at the effect of the first few months of World War II on an upper-class British family.
The second option is How Green Was My Valley from director John Ford and starring Maureen O'Hara and Roddy McDowall as members of a Welsh mining family at the turn of the century. I'll admit that neither of these films are quite as lavish as Gone With the Wind, but, frankly, the extravagance of that film at the expense of likable characters or a reasonable storyline is part of what turn me off about that movie in the first place.
Well, that's it: one hundred movies and then some as I reminisced about the AFI Top 100 Films of all time. Were there any there you haven't seen that appeal to you now?
There are a number of my favorite films that are ineligible for the list, because only American-made (or co-made) films can be included on the list. One such ineligible film is The Day of the Jackal (1973), a British-French production based on Frederick Forsyth's thriller about a slick assassin hired to kill Charles de Gaulle. It was very (very) loosely re-made simply as The Jackal (1997) - not a bad film in its own right, but far inferior to the original.