Marvel Studios/Disney

For many Marvel fans, "Captain America: Civil War" is a fan favorite. It's basically an "Avengers" movie in disguise, with a proper co-starring role for Iron Man alongside Steve Rogers. Upon its release in 2016, it felt momentous — a major turning point in the larger MCU narrative. But looking back on the film now, it doesn't hold up quite as well. The arbitrary choosing of sides, the whole Sokovia Accords situation, it all feels a bit ... contrived. Still, it's a fun movie, and two highlights are Chadwick Boseman's debut as Black Panther and Tom Holland's debut as Spider-Man.

Both characters are great here, though T'Challa gets much more substantive material. Spidey's really only brought in for essentially a stealth-pilot for his own series, then still yet to come. But even in his few minutes of screen time, Holland firmly establishes his own brand of swaggy, nervous-talking web-slinging, convincing moviegoers the world over that he was right for the part.

There's an argument to be made for this movie to rank higher here, but because Spider-Man only appears in a few scenes, and because its overall grandeur has faded a bit with time, it seems right that we start the list off with the character's first appearance in the MCU.

Sony Pictures/Marvel Studios

The middle entry in Tom Holland's original "Spider-Man" trilogy is one of the strangest movies in the entire MCU — not because it's bad (though some have made arguments against it), but because of its unique position within the larger franchise. This was both the follow-up to "Avengers: Endgame" and the final film of the monumental Phase 3, yet it's a pretty tight, self-contained coming-of-age story with few ties to the MCU writ large, save for all of the Tony Stark mourning.

Holland gets some of his most interesting material here, and it's especially fun to see him play opposite Zendaya's MJ as their relationship starts to take off. The film has more than a few surprises to subvert the typical expectations of such a story, which keeps things fresh, and Jake Gyllenhaal's Mysterio makes for a pretty compelling villain.

"Spider-Man: Far From Home" ends up being overshadowed by the timeless simplicity of its predecessor and the emotional bombast of its successor, but it's still a solid film, especially if you're mostly tuning in for Holland in particular.

Marvel Studios/Disney

Okay, yes, I said at the top that the amount of "Spider-Man" in a movie would impact its ranking on this list, yet here sits "Avengers: Endgame" above one of Holland's own solo films. "Endgame" has even less of the webhead than "Civil War," and there's an argument to be made that it doesn't really even fit here.

But come on. It's "Endgame," y'all.

This is very much Iron Man's movie, and his arc ties in closely to Peter's, which is one case for this earning a slightly higher spot on a Holland list. It's also just nice to see your friendly neighborhood Spider-Man back from the dead after a famously brutal end in "Infinity War." But the real explanation here is that "Endgame," for all its indulgent pomp and circumstance, is still a really fun movie. It has big weight and carries it off well, and it's better than the prior two entries on this list.

Is this one that I go back and rewatch all the time? No, and certainly not for its use of Spider-Man. But it's still one of the most important movies in the entire MCU, and it's still a grand old time.

Sony Pictures/Marvel Studios

"Spider-Man: Homecoming" lacks the explosive crescendos of many of the other entries on this list, but that's often to its benefit. The film has been overshadowed in the escalation of the superhero movie arms race, but when it came out, it was a breath of fresh air: an easy, universal hit that everyone seemed to love. It was uncomplicated and uncontroversial — the perfect, accessible blockbuster. And most important of all, it absolutely nailed Spider-Man himself.

Tom Holland is just so dang endearing here. While he certainly built on this particular performance over his subsequent Marvel films, this is where the trove of goodwill was first garnered. In every scene, he just feels right in the role, and the story stays grounded enough to let Peter Parker really shake out and develop as a person before he has to be an action star.

I very nearly put this movie even higher on this list, just because I think its simplicity makes it severely underrated. This is a movie you can go back to again and again and still have just as much fun with it. But I also can't pretend there haven't been multiple better "Spider-Man" movies since. For that reason, it stops here at the bronze medal spot.

Marvel Studios/Disney

I really wanted to put "Infinity War" at the top of this list, both because I believe it to be the best film in the MCU, and because Tom Holland's Spider-Man has some of his best material in it. In the end, I decided that a Spider-Man movie should top the list of Spider-Man movies (what a concept, right?), but "Infinity War" is still so, so good.

"Endgame" may have been the victory lap, but this is where the whole premise of the MCU, the multi-phase buildup, and all of the overarching storylines proved that it was worth it. A lot of that falls on Josh Brolin turning in an all-timer performance as Thanos, but pretty much every core character in the franchise gets great material here, with Tony Stark and Spider-Man sitting at the heart of the film.Their journey away from Earth — one that feels far more dangerous because of Peter Parker's rookie superhero status — is the most engaging individual storyline in the movie, and it ends with a tragic moment that left everyone walking away in mourning.

"Mr. Stark, I don't feel so good."

Did we know even at the time that he would be back? Yes, of course. Holland was still under contract for more movies. The truth was obvious. Even still, the relationship between these two characters makes the moment hit, and in the two-plus hours leading up to his death, Spider-Man has some excellent scenes.

Sony Pictures/Marvel Studios

For many, this is the definitive Spider-Man movie. I mean, it has all three of them, right? That alone would have made "No Way Home" an impressive spectacle, but it's far more impressive that the film takes the return of Andrew Garfield and Tobey Maguire and uses them to craft a cohesive thematic story about sacrifice, making mistakes, and moving beyond your darkest moments.

Holland has some heartbreaking moments here as his quest to bring peace to former Spider-Man villains repeatedly blows up in his face. And yet, he doesn't lose sight of the goal. He tries to be a hero, even to the worst people, even when it's impossibly hard. And when one of those villains pushes him over a line, his fellow Spider-Men are there to pull him back from the brink.

The emotional crescendo of this movie arguably belongs to Garfield and not Holland (you know the part), but that doesn't detract from his performance. It's a great all-around final beat for his character arc through the MCU, turning him from a junior hero into a fully fledged leader who understands the gravity of the work he does.

We can't wait to see how Tom Holland's return in "Spider-Man 4" builds off of the ending of "No Way Home."