It’s incredible that Tom Holland has been playing Spider-Man for 10 full years. It seems like only yesterday that the historic union between Marvel Studios and Sony, following a pair of disastrous Andrew Garfield-led outings, was forged, allowing Holland’s Peter Parker to exist in his own movies and hop over to the MCU. (It also allowed, perhaps less critically, for Marvel Studios characters to be central figures in his Spider-Man solo outings.)
Tobey Maguire, still maybe the most iconic actor to don the red-and-blue spandex, for example, only had the role for five years, starring in three movies for Sam Raimi between 2002 and 2007. Garfield just made two movies, two years apart, in 2012 and 2014. That makes Holland not just a beloved Spider-Man but someone who has grown up alongside the character; a true Friendly Neighborhood Spider-Man turned global ambassador.
And with the release of his latest web-slinging outing, “Spider-Man: Brand New Day,” we thought we’d look back at every time Holland shot webs, made pithy one-liners and got mentored by an older, more seasoned superhero, ranking his appearances from worst to best. Excelsior!
7. “Avengers: Endgame” (2019)
It’s not that Spider-Man’s involvement in “Avengers: Endgame,” one of the most popular movies of all time, is bad, exactly. It’s just that he’s not in it much, seeing as he – spoiler alert! – was turned to dust in the final moments of “Avengers: Infinity War” and only returns to the action for the climactic final battle (but what a battle it is!) and Tony Stark’s teary funeral. Still, Holland makes the most of the little screen time he’s given, with a properly emotional reunion between Robert Downey Jr.’s Iron Man and the young man from Queens whom he mentored and tried to keep safe. Leave it to Holland to give a chaotic, three-hour, $300 million extravaganza elegant grace notes and tender underpinnings. This is his magic.
6. “Spider-Man: Far From Home” (2019)
There is a lot to love about “Spider-Man: Far From Home,” including some of the most robust action sequences in the series and a wonderful, winking performance by Jake Gyllenhaal as Mysterio, a supposed hero but actual huckster and eventual supervillain. But there’s also just as much bad about “Far From Home,” which ultimately feels like a movie that Sony and Marvel Studios had to make instead of one that they wanted to make. The fact that large swaths of the movie feel like a kooky European teen sex comedy is the biggest indicator, as is the awkward Nick Fury-as-Skrull reveal, which does much to negate his warm mentorship in the rest of the movie.
Still, the idea that Peter Parker is adrift following the death of his hero and friend Tony Stark is pretty powerful. And Parker’s outing as Spider-Man at the end is a great twist. Holland does a lot with a little here, bless him.
5. “Avengers: Infinity War” (2018)
Yes, “Infinity War” is great and yes, Holland is great in “Infinity War.” (The sequence when Peter’s school bus passes by a giant UFO in New York and the hairs on Peter’s arm stand up is still one of the more unforgettable scenes.) But it’s also kind of a bummer that just a year earlier he was introduced in his first standalone movie as a “street-level” hero and now he’s traversing time and space with Tony Stark and Dr. Strange (in a slick, robotic suit no less). It feels like an odd betrayal of both the character and the mission statement for that character, even if it is tons of fun to watch Parker go up against alien wizards and galactic gods.
Still, Parker’s passing at the end of the movie, his whimper in Stark’s arms as he’s blipped to oblivion, remains one of the most touching moments in the entire Marvel Cinematic Universe.
4. “Captain America: Civil War” (2016)
The “Captain America” solo movie that was also a crazy team-up cluster cuss got to introduce both Black Panther (the late, great Chadwick Boseman) and Holland’s Spider-Man. How about that? Forget the logic problems of Tony Stark recruiting Spider-Man when, say, Luke Cage was also in New York City at the same time; the scenes between Downey Jr. and Holland are electric, setting up their dynamic for the rest of the MCU, and Spider-Man’s participation in the German airport battle, is so, so much fun. For the first time in a long time, Peter Parker felt like an actual kid instead of a man in his thirties cosplaying gawky awkwardness. In those early moments between Downey and Holland, a star was born. And an entire generation met their Peter Parker.
3. “Spider-Man: No Way Home” (2021)
One of the most popular movies ever, “Spider-Man: No Way Home” gave Peter Parker a terrific mentor figure in Benedict Cumberbatch’s Doctor Strange, and provided the movie with a device that allowed for a live-action “Spider-Man: Into the Spider-Verse” dynamic, as both Garfield and Maguire made their way to Holland’s world (and, indeed, the MCU). This is a movie that had built-in applause breaks for the audience reaction. And with good reason. It was a phenomenon.
But the real power of the movie, reiterated by the scenes borrowed for “Brand New Day,” is the decision that Peter makes at the end of the movie: to have Strange cast a spell that allows everyone who has ever known him to forget he ever existed. It’s heartbreaking and tragic and gives the movie, set at Christmas, a lovely, melancholic aura. This is a movie that has some of the most visually arresting sequences in the entire franchise (particularly that reality-bending chase with Strange) and some of its most drab compositions (every time they just cut between Spider-Man actors instead of luxuriating with them in the same frame).
2. “Spider-Man: Homecoming” (2017)
The promise of a new era begins. With “Spider-Man: Homecoming,” the conceit of street-level superhero movie really paid off. After his romp with the Avengers, Tony Stark won’t even return Peter Parker’s calls. A new villain has shown up using alien technology that the Avengers didn’t pick up after the Battle of New York. And he can’t even get the cute girl in school (Laura Harrier, sadly absent from subsequent films) to notice him. And from this foundation, Holland and director Jon Watts built one of the most emotionally nuanced portraits of the character to date – a kid who is just trying to do his best as both a high schooler and a superhero. Everything about it just works.
Michael Keaton’s Vulture is one of the MCU’s great villains and the reveal that Keaton is Harrier’s father is simply incredible. (The scene between Keaton and Holland in the car afterward is even better.) It proved that a Spider-Man movie could be a superhero epic as much as a coming-of-age high school movie and be even better because of it. “Spider-Man: Homecoming” remains one of the highlights of the entire MCU.
1. “Spider-Man: Brand New Day” (2026)
Holland’s latest turn as Peter Parker is also his best. Director Destin Daniel Cretton places a premium on Parker’s emotional journey as a young adult who also happens to be a superhero and one who has had all of his loved ones forget he ever lived. This is the lonely, existential Spider-Man that we crave. And if all of that wasn’t enough, he’s going through a physical metamorphosis too, as the spider threatens to overtake the man. There’s also a crazy new villain in town that can leap their consciousness between people.
What makes “Spider-Man: Brand New Day” the best, most compelling entry in the Holland saga and, indeed, Holland’s best performance as the character, is how Cretton (and uncredited screenwriter Justin Kuritzkes) foreground Parker’s emotional journey above all else. Even the cameos from other MCU characters, including a supporting turn from Jon Bernthal’s Punisher that shouldn’t work but ends up being one of the movie’s many highlights, serve to reinforce Parker’s arc. Everything is in service of the movie’s thematic concerns about change and growth, about learning that the institutions that say they are protecting you might be doing something much worse, and about learning to be your own person, which doesn’t necessarily mean doing it alone.
It’s an exhilarating, joyful ode to the character and, 10 years in, makes you wish Holland would never retire. It also makes you excited about the future of the MCU, which is something that we haven’t said for a very long time.
