Iron Man - This stealth game changer completely altered Studio filmmaking for the next twelve years (and counting). At the time, no one would have guessed that this little actioner from a start up studio would change film the way it has. Did it change things for the better, I would largely wager no, but it is undeniable that Marvel Studios has made some fantastic films and their 22 film narrative from Iron Man to Endgame is generally incredible. The thing is, this film single-handedly supports the full heft of the Marvel Studios grand plan which would end up being known as The Infinity Saga and does so through the use of subtle world building and focusing on character. At the end of the day, that is what this movie is; a character study of a man who finds a purpose in his life when his life is nearly stripped away from him. Robert Downey Jr owns this movie. His performance should have garnered Oscar attention (he did receive a nom for another film on this list, but this is the role that redefined his career and he is phenomenal in the role). Downey is to Iron Man the same way that Christopher Reeve is to Superman. The two are one. I am sure you can recast the role with other actors that would be serviceable (and they may well do so in the future...who knows) but this performance will forever be linked with this cinema icon. Jon Favreau helmed the production and did so in quite a unique fashion; he shot it through the use of heavy improvisation, almost like a Robert Altman film and by doing so, the film feels continuously unexpected and fresh. It hits a lot of the beats of a superhero origin story but does so from unique angles. Downey's ability to find sympathy in a film about a pretty not great man who discovers and slowly begins to earn his greatness (a character arc that would span the full Infinity Saga) speaks volumes. Unlike Batman who harnesses his pain into a superhero, or Superman who is just a good dude or even Spider-Man--the nerdy kid who just tries to do some good after petty revenges reshapes his worldview, Tony Stark is not a man you should root for. He is a womanizing, egotistical, brat kid who willfully creates weapons to take life on a mass scale. And, unlike most heroes, once he starts down the heroes path, he doesn't immediately change every one of his negative traits. He is allowed to be a flawed person throughout the story. His ego never shifts. He stops being a womanizer, but is also not the greatest man to the singular woman he loves. Flawed heroes will be what guide the MCU characters and Iron Man is the sturdiest example of them and you want to watch to see what character growth comes from them. At the time of release, this was my second favorite superhero film hands-down. It would get usurped two months later by another film on this list. But even still, this film is one of the best of the genre and rests just outside my top five comicbook movies. Check out my FULL REVIEW if you want to a more in depth analysis of the film.