5 Best Marvel Supporting Characters In Tom Holland's Spider-Man Movies, Ranked

With "Spider-Man: Homecoming," a new era of Spider-Man kicked off. While Sony/Columbia Pictures had been making Spider-Man movies since 2002,  "Homecoming" marked the first time that the studio's Spider-Man titles could directly interconnect with other Marvel movies. Thus, "Spider-Man: Homecoming" featured Tony Stark (Robert Downey Jr.) and Happy Hogan (Jon Favreau) from prior Marvel Cinematic Universe movies. This established a trend of each Tom Holland Spider-Man movie containing at least one MCU character, if not multiple figures.

Thus, Holland's Peter Parker/Spider-Man has encountered everyone from Bruce Banner/The Hulk (Mark Ruffalo), Nick Fury (Samuel L. Jackson), Wong (Benedict Wong), and so many others. These crossovers harkened back to the very first issue of Spidey's first solo comic series, "The Amazing Spider-Man," in which Spider-Man tried to join the Fantastic Four. That's a tradition the Holland Spider-Man movies have carried on dutifully to varying degrees of success.

The five best MCU supporting character appearances across Tom Holland's solo Spider-Man adventures (ranked below from "least best" to best) display the greatest intersection of various corners of MCU mythology. These appearances make Spidey's encounters with other superheroes exciting rather than cumbersome, while bringing out new sides of his personality. In other words, these MCU guest stars show how to do crossovers right.

Every movie could be improved with Florence Pugh. Even the best movies that are over five hours long would've gotten an extra star or two if they'd made room for Pugh. Thus, it was tremendously exciting that the surprise "Spider-Man: Brand New Day" Avengers cameo was none other than Pugh reprising her role as Yelena Belova/Black Widow from "Black Widow" and "Thunderbolts*." She's the source of valuable intel for Spider-Man (she is a member of The New Avengers now, after all), forcing the superhero to entirely disrobe (save for his underwear and mask) to join her in her sauna "headquarters."

Pugh's cheeky demeanor in "Brand New Day" is quite fun on its own merits. What makes it extra enjoyable, though, is that Belova is the rare character that can keep Spider-Man on his toes. While this costumed web-crawler cracks wise and drives foes like Tombstone (Marvin Jones III) up the wall with his quips, Belova's unexpected sauna-based demands and "small potatoes" talk turn the tables on Spider-Man and leave him bamboozled.

Beyond those traits, Pugh's Belova appearance in "Brand New Day" also works well as a standalone performance, not feeling the need to set up future MCU offerings. Plus, her presence ensures "Brand New Day" featured Florence Pugh, who benefits every movie she touches.

After Tony Stark served as a mentor to Peter Parker in "Captain America: Civil War," it was inevitable that Robert Downey Jr. would come back for the web-crawler's first solo movie. In "Spider-Man: Homecoming," Stark is a decidedly supporting figure taking on a genial uncle presence in molding Parker's superhero exploits from afar. Parker's hopes of breaking out of Stark's restrictions drives a lot of the "Homecoming" drama, as this teenage superhero yearns to prove to Iron Man that he's capable of handling much more.

When looking at all of Marvel's Phase Three movies, one interesting thing that crops up is how they allowed Robert Downey Jr. to inhabit new kinds of roles as Tony Stark. He's an adversary in "Captain America: Civil War," while in "Homecoming" he's decidedly a supporting player to a story focusing on Peter Parker. He doesn't overwhelm the film and entirely exists to service the younger MCU lead. In that regard, Robert Downey Jr. proves perfectly solid with the material he's handed. 

The best touch of this particular performance is Downey Jr. constantly keeping viewers unsure if Stark actually cares for this teenager (albeit in a quippy, sometimes aloof fashion) or is ignoring Parker's potential. It's some fresh territory for Stark's character, and Downey Jr. handles it well.

Steve Rogers/Captain America (Chris Evans) is never physically in the same space as Peter Parker in any of his solo Spider-Man adventures. However, he does have a memorable "Homecoming" appearance involving a series of instructional videos that are played for various purposes in Parker's high school. Sometimes it's for a fitness challenge during gym class. Other times, it's to help students think over their actions during detention. Whatever the occasion, this school has a Captain America video ready to go.

The concept of the rule-following Captain America headlining these kinds of segments alone is hilarious. Chris Evans is a hoot, executing these appearances with such sincerity and deeply realistic verbiage. To boot, this is a creative way of incorporating Captain America into Peter Parker's life. Hauling out arcane videos for educational purposes is such a classic school experience and it's inevitable Parker would encounter this during his teenage exploits. 

However, the presence of Evans in "Homecoming" takes on an extra dimension of amusement once the movie ends. The post-credit scene sees Evans' "Homecoming" role garner meta-levels of joy, as Captain America stares straight down the camera and lectures viewers about "patience." For those waiting for some "Avengers: Infinity War" tease, it's a perfect and hilarious subversion. 

For some, Doctor Strange's (Benedict Cumberbatch) actions in "Spider-Man: No Way Home" made no sense. While his presence may have inspired some confusing moments, Doctor Strange's role was overall successful. For starters, the buttoned-up, middle-aged Strange makes for a great contrast to the plucky, teenage Peter Parker. Whereas Tony Stark often acts like a kid despite his age, Strange actually differs from Parker, which makes it fun to watch their demeanors clash.

Meanwhile, a mid-movie scene where Strange chases Spider-Man through the Mirror Dimension brings a new fun layer to their dynamic. Here, Strange becomes Elmer Fudd and Spider-Man becomes Bugs Bunny, with the latter superhero constantly outwitting his adversary against all odds. Watching this rapport play out is a riot, especially since Cumberbatch's deeply committed Doctor Strange performance makes for an amusing foil against Holland. Better yet, Cumberbatch's portrayal of Strange's quiet sadness over Parker's climactic sacrifice is one of the movie's most moving moments.

With Doctor Strange helping out (and briefly fighting) Spidey in "Spider-Man: No Way Home," two New York Marvel superhero legends collided. Benedict Cumberbatch's acting chops and the smart writing between the two characters ensured this union had more significance than just Spidey and Strange sharing a city.

Prior to "Spider-Man: Brand New Day" hitting theaters, questions abounded over how the gritty Frank Castle/The Punisher (Jon Bernthal) would work in a PG-13 Spider-Man adventure. The Punisher had anchored his own solo movies before, but they'd always been hard-R outings full of gore. His streaming TV show exploits had been similarly violent. How was this character going to work in the context of "Brand New Day?" Turns out, there was no need to worry. Castle didn't just work in "Brand New Day." He was one of its highlights, giving Bernthal his best Punisher appearance yet.

First and foremost, Holland's Spider-Man and Bernthal's Punisher are hilarious to watch as the two constantly bicker at one another. Bernthal and Holland's odd couple pairing informs the most humorous "Brand New Day" moments. Meanwhile, pitting Castle against more heightened Marvel Comics foes like The Hulk and Jean Grey (Sadie Sink) unleashes amusing new facets to the character. Watching The Punisher becoming immediately overpowered is an amusing sight, while him warming up to MJ (Zendaya) after initially being hostile towards her is equally charming.

The fact that Bernthal's Frank Castle actually works well as a source of poignancy by the ending of "Brand New Day" speaks to how successfully this grimy character was translated into PG-13 cinema.