Superhero movies have come so far over the past few decades that many of them have received trilogies, to varying levels of success. They’ve all done well commercially, but from a critical standpoint, finding truly great superhero trilogies can be difficult. Many of these series ended up with at least one disappointing superhero movie.
Of course, some of these trilogies feature two movies that are so good that even a disappointing entry doesn’t totally ruin it. They still stand the test of time as highly entertaining franchises. There are also a handful of superhero trilogies where each movie is fantastic, which stand out among the best movie trilogies, period.
Blade (1998-2004)
A lot of people don’t bring up Blade when it comes to important superhero movies. Before X-Men and Spider-Man were hits in the early 2000s, Blade found success in 1998 and opened the door for Marvel characters and superheroes in general to get more movies.
Blade was a commercial hit but was met with mixed reviews, though reception has gotten better over time, becoming something of a cult hit. Blade II is the peak of the series, giving us more action, Wesley Snipes at his best, and the great Guillermo del Toro in the director’s chair.
The only thing holding Blade back from ranking higher among superhero trilogies is Blade: Trinity. The film dealt with all sorts of problems in production, including disagreements between the director and Snipes, leading to many reshoots.
The end result was that Blade: Trinity was easily the worst installment in the franchise. However, fans still love the Blade character and he was brought back for a fun cameo in Deadpool and Wolverine, showing the staying power of the trilogy overall.
Wolverine (2009-2017)
While Blade was a strong trilogy that ended with a whimper, Wolverine’s trilogy went in the opposite direction. Hugh Jackman became a star as the character in the X-Men films and was given his own spin-off film in 2009, X-Men Origins: Wolverine.
The movie was a massive misfire due to production troubles, an incomplete screenplay, and a misunderstanding of several key characters. Thankfully, the series was given a chance to redeem itself, which it did spectacularly.
The Wolverine arrived in 2013 and is one of the more underrated superhero films of the time. It’s mostly a standalone story where Wolverine travels to Japan and battles samurai without his healing abilities. It makes for an exciting and fun action flick. Then in 2017, Logan topped them all and capped the trilogy in impressive fashion.
It stands as one of the best superhero movies ever made, features Jackman’s best performance, and introduced us to Dafne Keen’s X-23. The R-rating allowed them to showcase the violent nature of Wolverine and Logan was nominated for Best Adapted Screenplay at the Oscars.
Unbreakable (2000-2019)
When it comes to superhero movie franchises, a lot of people tend to overlook Unbreakable since it’s not based on any popular comic book character. Instead, it’s a completely original story by M. Night Shyamalan, and it’s different from most superhero stories.
Unbreakable was a big hit upon arrival, though it wasn’t an action-packed superhero film, instead working as more of a character study. Unbreakable, starring Bruce Willis, felt like a standalone story that would never be revisited again, but that changed in 2016.
Shyamalan returned to form with Split, which was also a critical and commercial hit. The movie was great on its own, but right before it wrapped, Willis popped up and revealed this was a secret sequel to Unbreakable. The franchise had delivered two great movies.
2019’s Glass wrapped the story up, bringing Willis’ character face-to-face with James McAvoy and reuniting him with Samuel L. Jackson. Unfortunately, many viewed the film as underwhelming. Had it been better, Unbreakable could’ve been much closer to the greatest superhero trilogy ever.
Sam Raimi’s Spider-Man (2002-2007)
While Blade and X-Men were hits of the era, it was Spider-Man that really got the superhero craze going. The film was a massive success with a huge opening weekend and gave fans plenty of iconic moments, making Tobey Maguire the favorite Peter Parker for so many.
Spider-Man was great but then Spider-Man 2 took things to new heights. To this day, even after so many films have come out focusing on the wall-crawling superhero, many consider it to be the best Spider-Man movie ever made.
Some even consider Spider-Man 2 to be the best superhero movie ever made. Memorable action setpieces, a great villain, and a gripping, emotional story made it a hit. Fans were excited for the third entry but it didn’t live up to expectations.
Spider-Man 3 was panned by fans for the odd character choices, like the much-memed dancing sequence, overstuffing the screenplay with too many villains, and sluggish pacing. Some look back on it as a fun film, and while it’s the worst of the three entries, Sam Raimi’s Spider-Man remains a strong trilogy.
Iron Man (2008-2013)
The MCU doesn’t become the juggernaut that it is today without the success of 2008’s Iron Man. The franchise made the gamble of casting Robert Downey Jr. as Tony Stark, given the actor’s controversial history, yet it paid off wonderfully.
Downey Jr. gives a rock star performance that helps carry Iron Man and make it endlessly rewatchable. It’s a turn that let everyone know he was the right man to lead the franchise into the future.
Iron Man 2 is a solid sequel that does get bogged down by shoehorning in some world-building for the greater MCU. Iron Man 3 is where things get dicey, though, because some fans still dislike it today, mostly for the famous Mandarin twist. While your feelings on that twist can vary, the rest of Iron Man 3 is pretty great.
Shane Black’s signature style is all over the place, the action is inventive, and we get to see Tony deal with PTSD. The highlight is seeing Tony’s genius come into play as, with his suits malfunctioning, he has to get clever about how to survive most scenes.
Deadpool (2016-2024)
The aforementioned X-Men Origins: Wolverine featured the on-screen debut of Ryan Reynolds as Deadpool, but they got the character completely wrong. Reynolds fought for years to get the right version greenlit and he finally did to great success in 2016.
Deadpool marked the start of a great, highly rewatchable franchise. Reynolds perfectly embodied the personality of the “Merc With a Mouth,” breaking the fourth wall, cracking jokes, and making sure nothing was off the table.
Its success led to Deadpool 2, which was another hit that included a wild Brad Pitt cameo, major characters like Cable, and even more fourth wall breaks. When Fox was sold to Disney, many believed the franchise was done.
However, Disney gave us a third film that brought back Jackman’s Wolverine, Deadpool & Wolverine. It integrated the characters into the MCU and didn’t change anything that had made Deadpool a hit in the first place. It’s one of the few superhero trilogies where every entry is legitimately good.
Captain America (2011-2016)
A lot of trilogies can feel like three totally separate movies, but the MCU managed to make the Captain America trilogy feel like one cohesive story. Each film goes so well with the others, even if the first mostly takes place way back in 1942.
Captain America: The First Avenger is one of the MCU’s better origin stories with one of the franchise’s best endings. The Winter Soldier holds up as the best MCU movie ever in the eyes of a lot of fans, feeling like a superhero take on the political thrillers of the ’70s.
Civil War takes it up a notch, feeling like The Avengers 2.5, given how many characters were involved. Despite those different aspects, each film focuses on Steve Rogers’ desire to do what’s right in the face of adversity and his relationship with Bucky Barnes.
It’s rare to find a trilogy with no misses but that’s the case here. Each installment of the Captain America trilogy was met with widespread acclaim and they each offer something different despite sharing many common themes. That’s a difficult trick to pull off.
The Dark Knight (2005-2012)
When Batman Begins arrived in 2005, it was unlike anything we had seen in the superhero genre. This was a raw, gritty origin story for Batman, completely stripped down and much more serious than the Joel Schumacher films that preceded it.
In a lot of ways, Christopher Nolan’s work on Batman Begins helped revitalize the character in pop culture. Then, The Dark Knight arrived and really changed everything. It’s considered by many to be the greatest superhero movie ever made.
Part of why The Dark Knight is special is that it doesn’t feel like a comic book film a lot of the time, instead coming across as a gripping crime drama. The movie earned a rare Best Picture nomination for a superhero movie and Heath Ledger won a posthumous Best Supporting Actor Oscar for his turn as the Joker.
The Dark Knight Rises grossed over $1 billion, just like The Dark Knight, and though it’s a step down from the first two movies, it was still really good. It holds an 87% Rotten Tomatoes rating and remains one of the most ambitious superhero movies ever in terms of sheer scale.
Guardians Of The Galaxy (2014-2023)
Anyone who needs proof of the MCU’s popularity and power can look to Guardians of the Galaxy. While the MCU had hits with things like The Avengers, this was a group of D-list comic book characters that were a hard sell, given the wacky cast of characters, including a talking raccoon and a walking tree.
However, Guardians of the Galaxy defied expectations to become a huge hit, and those wacky characters are among the most beloved in the MCU today. The first film expertly blends weird sci-fi action with comedic beats and just the right amount of emotion.
Guardians of the Galaxy Vol. 2 took things up a notch, giving us more action, even harder-hitting emotion, and helped set the stage for these characters appearing in Avengers: Infinity War and Avengers: Endgame.
It took several years and a James Gunn firing and rehiring before Guardians of the Galaxy Vol. 3 arrived, but it stuck the landing. The third straight critical and commercial hit, Guardians of the Galaxy Vol. 3 wrapped up the trilogy neatly, giving each character a fitting ending.
MCU Spider-Man (2017-2021)
While Sam Raimi did great work with Spider-Man, the MCU was able to top it. Tom Holland is perfect as Peter Parker and while some of his best moments came in team up films like Avengers: Infinity War, his solo films are remarkably consistent.
Spider-Man: Homecoming is a fantastic story of a kid trying to live up to high expectations, getting in over his head, and overcoming the odds. There’s a great small role from Robert Downey Jr., and an incredible villainous turn from Michael Keaton as The Vulture.
Spider-Man: Far From Home is the least beloved of the three but is still fantastic. Jake Gyllenhaal makes for a great villain, the teen rom-com subplot between Peter and MJ is heartwarming, and the post-credits scene is an all-timer.
Spider-Man: No Way Home is the most ambitious of the three, bringing back villains from past live-action films and marking the return of Tobey Maguire and Andrew Garfield. The movie is far from a cameo-fest though, telling a personal and emotional story for Holland’s Parker. Together, it makes for the greatest superhero movie trilogy.
