10. Iron Man (2008)
It’s hard to imagine what the superhero landscape would look like today had Marvel Studios not released Iron Man all the way back in 2008. The first in what is now a 23-film saga, the film wasn’t tasked with setting up an entire shared universe of superheroes – it just had to introduce us to its primary superhero.
A darker tale than the two Iron Men sequels, the film used Tony Stark to highlight how one man can undergo an extreme character development upon realising the error of their ways – and that’s exactly what happened here. Upon witnessing how dangerous his technologically-advanced weapons could be if they fell into the wrong hands, Tony took it upon himself to use that technology to create something instead. And just like that, Iron Man was born.
We could go on about the strength of the script here, but it would be ridiculous to overlook the fact that the film’s greatest asset was undoubtedly Robert Downey Jr. The charismatic actor didn’t just play Tony Stark; he became him and, in doing so, set the standard immensely high for every hero that would follow him.
In spite of its compelling narrative, Iron Man kick-starts that Tony Stark tradition of not taking itself too seriously and thus, it’s also a whole lot of superhero fun – highlighting that Marvel had found the perfect formula for their empire.
9. Captain America: Civil War (2016)
The final installment of Captain America’s standalone trilogy didn’t feel all that standalone due to the sheer amount of Avengers that featured in it, but it was, at its heart, about one man’s never-ending bid to overthrow the powerful to protect his best friend. And if you really think about it, that’s all the Captain America movies have ever been about – and, perhaps more importantly, why they always worked.
Civil War owes a lot to its predecessors, borrowing its serious tone and government-heavy premise from The Winter Soldier – which, of course, adds depth (and context) to Steve’s reluctance to sign the Sokovia Accords. In doing so, it cleverly manages to weave some of the MCU’s strongest and most powerful long-running narratives into the story.
From Cap’s attempts to protect Bucky, to Tony’s desire to get to the truth, the plot is expertly-engineered in such a way that it’s hard to outright root for one side and, although it is Steve who is ultimately right about everything, it’s hard not to feel for Tony at the same time. And that, ladies and gentlemen is some beautiful internal conflict – much like that which the characters felt throughout the movie.
Of course, we can’t praise Civil War without referencing the wonderful battle sequence which saw Team Cap and Team Iron Man collide (while also introducing Spider-Man) and, in doing so, gave us the best battle the MCU had ever seen (at the time).
This was, very much, the end of the MCU as we knew it – and what an unforgettable way to go out.