Ranking Rocky
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It is a grounded, resoundingly human look at integrity and persevering, and serves as an authentic, affecting American dream fable that showcases one's deep drive to make something of themselves — despite their impoverished background — and to prove to the world they have greatness with them. As you can imagine, Rocky is a deeply personal movie for Sly Stallone, and it's impossible to imagine any other actor playing this role with the same astounding resonance.
...it's ultimately Rocky's relationship with Adrian that really makes Rocky such a great and everlasting movie. Through their hard-luck relationship, there is a beautifully human relationship between them, one that is emotionally felt and sincere in its presentation.
This.
I was going to be upset if the original Rocky wasn't listed first. I watched it a few years ago after a long time having not seen it... I forgot how authentic, raw, and sincere it felt. For example, the philadelphia morning exercise routine. Felt very relatable to anyone who's gotten up at 5am for a pre-dawn workout. Add in the struggles Sly went through to get the movie made, for it to go on and win so many awards. Great cinema.