Robert Downey Jr. has had a very colorful career in Hollywood. Considered by some to be a member of the “Brat Pack,” his face appeared in a number of comedic films (many of which, sadly, aren’t that great). After his well-publicized struggles with addiction, it might have seemed that his career was over. However, through some well-chosen roles he managed to restore his star persona to its former glow and, with his role as Tony Stark, he actually managed to become something of a cinematic icon.
Throughout his career, he’s managed to be in some very good and also some very bad films.
Worst: Danger Zone (1996): 4.5
The action film is one of those genres that it’s very easy to badly, and this film illustrates why that rule holds true. Starring Billy Zane and Downey, it takes place in an African country and involves a rather convoluted plot about civil war and toxic waste dumps. It’s honestly a bit of a hot mess of the film, and it’s a vivid illustration that, at this point in his career, Downey was struggling a bit to find relevant roles.
Best: Captain America Civil War (2016): 7.8
There’s no question that Captain America: Civil War is one of the more sophisticated movies in the MCU. In large part this is because it focuses on the long-brewing conflict between Captain America and Iron Man, both of whom have their own ideas of what the Avengers should be doing and the role that they should be playing. Chris Evans and Downey really do strike sparks off of one another, and it’s great to see their very different acting styles collide in epic fashion.
Worst: The Shaggy Dog (2006): 4.4
For some reason, the 2000s saw a number of remakes of classic live-action Disney films. Unfortunately, many of them landed with quite a colossal thud, and The Shaggy Dog reveals why that is true.
Thankfully, Downey doesn’t play the titular role (that dubious honor goes to Tim Allen), but the film truly lacks any trace of originality or inspiration, and it’s hard to imagine why anyone in the studio thought that this remake was in any way a good idea.
Best: Iron Man (2008): 7.9
Iron Man is where the juggernaut that is the MCU got its start, and it explores the events that led up to Tony Stark becoming the titular superhero. It’s a truly great film, in large part because Stark’s own character progression seems to have quite a lot in common with Robert Downey Jr.’s. In fact, it’s probably because he has had such a haunted past that he manages to imbue this character with so much depth, richness, and pathos.
Worst: Too Much Sun (1990): 3.9
Anyone who has seen a number of films made in the 1990s (particularly the early years of that decade) knows that it was truly a strange time for comedy. This film is one of the weirdest ones out there, since it focuses on a wealthy man who wants either of his gay children to produce a grandchild. The comedy doesn’t quite land, even though it was actually directed by Robert Downey Sr.
Best: Avengers (2012): 8.0
If the earlier films in the MCU hadn’t already demonstrated that this was a box office juggernaut, then The Avengers certainly did. It’s not hard to see why the film became so enormously popular. It brings together all of the best-loved members of this fighting group, and the visuals are, simply put, some of the most stunning to be seen on screen. It’s a big-screen extravaganza that is definitely worth the price of admission, and the film still holds up, even eight years after it came out.
Worst: Rented Lips (1988): 3.9
At first glance, this film might look like it was designed to be good. It’s directed by Robert Downey Sr. (whose reputation for creating satires is well-deserved), and it stars not only his son (who has his own charisma) but also the comedically brilliant Martin Mull and Kenneth Mars.
Unfortunately, it is a rather disastrous film, in part because so much of the comedy moments just don’t seem to come together in the way that the director clearly intended.
Best: Avengers: Infinity War (2018): 8.4
It’s a very rare franchise that manages to keep its critical and commercial potential going right into the final installments, but Avengers: Infinity War is a further demonstration, if any were needed, that the MCU had what it took for the long haul. The titanic clash with Thanos, toward which the entire series has been building, reaches its climax here, as he finally manages to wipe out half of life in the universe. And through it all Downy manages to imbue his Tony Stark with all the tortured pathos that every epic hero deserves.
Worst: Hail Caesar (1994): 3.2
One would be forgiven for thinking that a film that not only stars Anthony Michael Hall but was also directed by him might be at least somewhat funny. Unfortunately, this film is a brutal illustration that just because someone is a good comedy actor doesn’t mean that they necessarily know how to direct a comedy film that actually manages to be funny. It is, quite frankly, something of a slog to get through.
Best: Avengers: Endgame (2019): 8.4
At last, in Avengers: Endgame, the wait was over, and it was definitely worth it. The Avengers finally manage to effectively join their forces and bring Thanos down, undoing his destruction of half of life in the universe and restoring many of the best-loved Marvel characters. In the process, however, Iron Man sacrificed his own life so that others could be saved. It was, of course, the endpoint toward which his arc had been moving since the very first film, but it was still a wrenching moment and one can’t help but weep at the loss of this noble, tragic figure.