The irony is that I'm a big fan of The Great American Songbook, so I lean towards films with Fred Astaire, Frank Sinatra, Gene Kelly, Bing Crosby, and others, but the newer titles are often much better and more interesting story-wise, much deeper and bolder, so they manage to get me more emotionally involved.
The latest musicals that I enjoyed were the new West Side Story, by Steven Spielberg, and especially Jonathan Larson's Tick, Tick... Boom!, directed by Lin-Manuel Miranda, which I loved. (I did not know about Larson at all until the release of that film.) The next one I'm planning to see is Larson's most famous work, Rent.
I have finally seen it on January 8th, and I definitely enjoyed it, but I have difficulties determining my opinion of it. It was good in every way, and some things were improved in comparison to the first film, but my general impression is still that it was somewhat unnecessary, in a way that I would have been thrilled with it if it was the first film version of the stage musical; this way, however, I feel like I would still rather watch the first film if I felt the need for West Side Story. I certainly enjoyed the direction and cinematography of the 1961 version more.
I have to say, though, that the performances of Mike Faist (Riff) and David Alvarez (Bernardo) were great and memorable, no matter how good the original actors were too.
The bottom line is that I would need to rewatch the 1961 and 2021 versions back-to-back in order to conduct a detailed comparison.