Good post. since you mentioned The Insider recently, I have to say that rewatching it last month was this for me, exact same feelings as when I saw it in high school : well-made but ultimately too predictable/obvious for me to care about any of it.
(On the other hand, I got a higher appreciation for many of the other Michael Mann’s I rewatched last year)
90% of the time a rewatch will have me feel the exact same, but it’s still worth to try…
And some of my favorite movies I only liked on my second watch (Vertigo, Heaven’s Gate), although this probably had a lot to do to only watching them on a small screen/bad quality the first time.
Speaking of rewatches, this is one I should try again. Old school Hollywood is something I wasn’t keen on when I was young, as I was more interested in movies where the director shows off with his visual style, or there is some sort of surprises/edginess, which you don’t see often in Hollywood 40s/50s. But for instance I rewatched “His Girl Friday” recently and loved it (unlike high school me). Maybe I’m at the point where I can understand why old school cinephiles adored John Ford / Howard Hawkes (neither really ever clicked for me).