Sylvester Stallone's 15 Biggest Movies - Ranked Worst To Best

4. Rocky Balboa (2006)

Here's where it starts to get tricky. My brief here is to rank Stallone's biggest hits from worst to best; and, speaking critically, Rocky Balboa may very well be a better movie than some of those ahead. However, one must also take into account who Stallone is. In a very real sense, he's a living legend, and that legend was built by particular roles and particular performances. The character of Rocky is without question the cornerstone of Sly's legend, but when we think of that character, is 2006's Rocky Balboa really the first film that comes to mind? The answer has to be no. It's a great film, and the first of the Rocky sequels to really remain true to the spirit of the 1976 original, but it's never going to hold the same iconic status. Still, Rocky Balboa surprised the world by demonstrating the then 59-year old Stallone still had all it took to take on his most famous role again, both in terms of acting and physical conditioning, and as a writer and director. It also made $155.7 million worldwide, making it his 14th biggest movie.