Tom Holland and Zendaya are one of Hollywood's most beloved power couples, both on and off screen. After tying the knot in 2026, they've continued to dominate the box office, with their latest collaborations, The Odyssey and Spider-Man: Brand New Day, becoming two of the year's biggest hits. But with five movies together under their belts, which one truly stands out as the best? We've ranked them all, from the least essential to the absolute must-watch.
5. Spider-Man: Far From Home (2019)
While Spider-Man: Far From Home is often considered one of the weaker entries in the live-action Spider-Man franchise, it's still a solid addition to the MCU. Picking up after the events of Avengers: Endgame, this film deals with the aftermath of the Blip, giving it emotional weight. But it's also a breezy European adventure, as Peter Parker tries to enjoy a school trip while battling elemental threats. It's the first Spider-Man movie to step away from New York, which is refreshing, but it also feels a bit like a stepping stone to bigger things. The romance between Peter and MJ begins here, making it a key moment for their relationship, but as a standalone film, it lacks the punch of later entries.
4. Spider-Man: Brand New Day (2026)
This 2026 blockbuster was a massive event, and for good reason. Spider-Man: Brand New Day finds Peter Parker navigating life after high school, and it's a more mature take on the character. Holland delivers his best performance as Spider-Man yet, and Zendaya shines as MJ, even though she doesn't remember Peter due to the spell at the end of No Way Home. The film balances emotional fallout with exciting action, and while it's not the best of the bunch, it's a strong entry that sets up future MCU threads. It's a must-see for fans of the couple.
3. Spider-Man: Homecoming (2017)
The first solo outing for Holland's Spider-Man is a breath of fresh air. Homecoming finally makes Peter Parker feel like a real teenager, with all the awkwardness and insecurity that comes with it. The film is low-stakes compared to other superhero flicks, but that's what makes it so charming. It's a coming-of-age story wrapped in a superhero package, and it's genuinely funny and relatable. Holland and Zendaya's chemistry is palpable even here, setting the stage for their real-life romance.
2. Spider-Man: No Way Home (2021)
This is the one that broke the internet. Spider-Man: No Way Home is a multiversal epic that brings together three generations of Spider-Men, and it's a love letter to fans. The film is packed with nostalgia, but it also has real stakes, as Peter makes a heartbreaking sacrifice to save the world. Holland and Zendaya's performances are top-notch, and the emotional core of the movie is their relationship. It's a rollercoaster of emotions, and it's easily one of the best Spider-Man movies ever made.
1. The Odyssey (2026)
Taking the top spot is Christopher Nolan's The Odyssey, a sweeping epic that reimagines Homer's ancient tale. Holland and Zendaya are part of an ensemble cast that brings this mythic story to life, and their performances are nothing short of spectacular. The film is a visual and narrative triumph, earning critical acclaim and box office success. It's a testament to their range as actors, proving they're more than just superheroes. If you only watch one movie featuring this dynamic duo, make it this one.
From high school hijinks to epic adventures, Holland and Zendaya have proven time and again that they're a cinematic force to be reckoned with. Whether you're a fan of their Spider-Man days or their more recent dramatic turns, there's something for everyone in their filmography. And with The Odyssey joining the billion-dollar club, it's clear their star power isn't fading anytime soon.
