Throughout the first three phases of the Marvel Cinematic Universe, Tony Stark/Iron Man was the closest thing to a central character. Robert Downey Jr. appeared in a total of 10 films throughout phases 1-3, including the first film of phase 1, Iron Man, and the climactic (though technically not last) film of phase 3, Avengers: Endgame.
One reason why phase 4 has felt a little directionless might be its lack of a "main character" like Tony Stark to keep things coherent and tied together. Whether there will be a figure like that emerging, or if Marvel has another plan altogether is yet to be seen. But now, with the first three phases of the MCU long in the past, it's possible to look back and properly assess all the films Downey Jr. appeared in during the first 11 years of the MCU, and rank them from worst to best.
Iron Man 2 (2010)
Iron Man 2 is strange. It's both an important piece of the overall MCU storyline, and hugely disappointing and unsatisfying as its own film. In this overstuffed film, Tony Stark fends off multiple new foes, deals with the public attention he's received since revealing he's Iron Man, and becomes involved in Nick Fury's Avengers Initiative, still in its early stages.
With solid ideas, Jon Favreau returning to direct after the successful first film, and a huge cast full of talented actors, Iron Man 2 should be so much better. But it's a messy, sloppy film that might have strong individual scenes, but as a whole, it fails to feel coherent. It is an important film for understanding the origin of the Avengers, but it's otherwise an MCU low point.
The Incredible Hulk (2008)
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Admittedly, the reasons The Incredible Hulk isn't the worst film Stark makes an appearance in are minor. Essentially, it's just a bit bland and forgettable, contrasted with Iron Man 2, which was a little forgettable but also really disappointing, and had more potential than the comparatively less ambitious The Incredible Hulk.
Still, Downey Jr.'s brief cameo in this film's post-credits scene does provide another early hint that a comic book-style interconnected universe is happening (even if the specific cameo itself doesn't get fleshed out later), and confirms the film is a part of the MCU. But overall, very little Tony Stark, and similarly, very few reasons to watch this, even if it's technically not awful.
Iron Man 3 (2013)
From this point on, things get pretty good and just keep getting better. Iron Man 3 improves on Iron Man 2 by dialing back the scale. Rather than juggling a huge number of plot threads and characters at once, the focus is on Stark and his physical and psychological problems following the events of The Avengers.
There may be fewer threats for Iron Man to tackle, and fewer ties to other movies in the MCU, but it's a more personal film for the character. It also allows Downey Jr.'s skills as an actor to really shine, and writer-director Shane Black injects a decent amount of comedy into the proceedings. Maybe not as entertaining or emotional as the MCU at its best, but it's still a good entry.
Captain America: Civil War (2016)
Captain America: Civil War is certainly ambitious, and while it's a fairly good MCU film, it doesn't quite live up to its full potential when it comes to the Avengers fighting out their differences in a civil war. There are some lasting consequences and decent action scenes to enjoy, but it doesn't shake things up as much as the title might make you believe.
One area of limitation is the portrayal of Tony Stark, given the film puts him on the side of the politicians/authority when he supports the Hero Registration Act, whilst Captain America doesn't. It feels like it should be the other way around, and while it's good the film is trying to tell a more serious story when it comes to Tony's traumatic past, it also gives him very few opportunities to be likably sarcastic or funny. Maybe it makes sense it fares better as a Captain America film, given his name is in the title.
Spider-Man: Homecoming (2017)
From here on, things are generally very good. Spider-Man: Homecoming was the first time the MCU's new Peter Parker could truly shine, after a brief but memorable role in Civil War. Tom Holland didn't disappoint, and the film is a fun and fairly light-hearted take on Spider-Man where he feels more like a kid than ever before, and the film itself plays out almost like a teen comedy/coming of age movie.
It also provides a good role for Tony Stark, who appears as a mentor of sorts for Peter; the oldest and most experienced member of the Avengers guiding its youngest recruit. It's a good movie overall, and kicked off a solid trilogy for Holland's role as the definitive Marvel superhero.
Avengers: Age of Ultron (2015)
Age of Ultron is the weakest of the four Avengers movies, but it still has more going for it than most viewers give it credit for. It reunites the core Avengers team to face off against Ultron, an AI gone mad, and introduces important characters for the future of the series, like the Scarlett Witch and Vision.
It might bite off a little more than it can chew, but it's good entertainment, and gives more for characters like Hulk, Black Widow, and Hawkeye to do than usual. And Tony Stark's role is interesting, too, given his responsibility in creating the film's titular villain.
Iron Man (2008)
This is the one that started it all. Iron Man tells the story of Tony Stark becoming the titular superhero in an efficient and entertaining manner that still holds up to this day. Viewers wouldn't have known it back in 2008, but it's amazing just how much has ended up following this one film.
It's also notable for being a comeback vehicle for Robert Downey Jr .himself, who was a controversial public figure at the time, to say the least. Tony Stark was arguably the role he was born to play, though, and all but cemented he would be the MCU's central character for the then foreseeable future.
The Avengers (2012)
The first Avengers film was also the first time a big superhero team-up movie was shown to work. While Iron Man officially started the MCU, The Avengers was instrumental in establishing its dominance, and Marvel is still riding the wave of cultural excitement it began, over a decade later.
It's a little quaint when compared to later Avengers films, but The Avengers is undeniably pure, fun, and excellent entertainment. It balances its characters well and maintains a fast pace, good action, and plenty of humor to distract from the surprisingly simple alien invasion storyline.
Avengers: Endgame (2019)
The last Marvel film Downey Jr. appeared in (for now) at least lets him and his character go out with a bang. Part of the reason it feels so climactic is that not only is the series' main villain up until that point defeated, but Iron Man - who's been there from the start - gives his life to do so.
Time will tell if phase 4 or any future phases will end as powerfully or definitively as this, but it's hard to ask for a better finale to phases 1-3. The fact Tony Stark's final line is the same in both Iron Man and Endgame is perfect, too.
Avengers: Infinity War (2018)
What more can be said, really, when it comes to showering Avengers: Infinity War in glowing praise? It throws so many characters into one movie while also giving a proper introduction to Thanos with a breakneck pace and somehow it just all works?
It's a minor miracle everything fits together so well, and its infamously dark ending will ensure it remains one of the most memorable MCU films for some time. As arguably the best MCU film, it also stands as the best film in those first three phases of the MCU that Iron Man appeared in.