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From 'Spider-Man' to 'Avengers': The 19 best movies to kick off the last 20 years of summer blockbusters

From superheroes to secret agents, we bring you two decades of sheer cinematic awesomeness.

By Josh Weiss
A collage including characters from Marvel, Star Trek, Star Wars, Mission Impossible, and Shrek.

You think the superhero craze in Hollywood is anything new? The summer moviegoing season has — for the most part — been defined by the comic book genre for two solid decades.

From the humble beginnings of Sam Raimi's Spider-Man 20 years ago, to the epic crossover event of Avengers: Endgame, we take a look back (in order of release) at the last two decades worth of crowd-pleasing popcorn flicks that officially kicked off their respective summer movie seasons. In a move that shouldn't come as a surprise to anyone, we will not be discussing 2020 on this list because A) there was no genuine blockbuster season and B) most of us would prefer that period of our lives never happened anyway.

Let's get the party started!

1. Spider-Man (2002)

Along with 2001's X-Men, Sam Raimi's first Spider-Man film helped kickstart the superhero movie boom that we continue to enjoy to this day.

It's not easy to tackle one of the most beloved comic book characters in history. With great power, comes great... well, you know the rest. Fortunately, Raimi's talent for juggling camp, emotion, and visceral terror turned out to be a perfect match for the material.

An earnest turn from Tobey Maguire as Peter Parker and a scene-stealing take on Green Goblin from Willem Dafoe make Spider-Man a timeless classic and, for some, a definitive cinematic interpretation of Marvel's friendly neighborhood web-slinger. It's no mystery as to why fans went absolutely nuts when Maguire and Dafoe showed up again in No Way Home.

2. X2: X-Men United (2003)

X2 is everything a blockbuster sequel should be: Bigger action set pieces and a deepening of the themes and character drama espoused by its predecessor. The motifs of prejudice and blind bigotry in the face of things humans don't fully understand take on new meaning as mutant-kind comes together to take on its greatest threat so far — William Stryker — a man who also holds the key to Logan's murky past. The brilliant execution of X2 is further highlighted by the jumbled misfire of the sequel that would follow three year later.

3. Shrek 2 (2004)

Since the 2004 summer season started off with a pair of underwhelming films — Stephen Sommers' Van Helsing and Wolfgang Petersen's Troy — the box office didn't really get a shot in the arm until the release of Shrek 2 on May 19. Continuing the first movie's clever subversion of fairy tale tropes, Shrek 2 dared to ask: “Ok…so what happens after happily ever after?”

The hit DreamWorks animated movie dominated all summer long as families' repeat trips to see Donkey and Shrek get the sequel treatment sold a lot of popcorn and broke then-records for an animated title. As of this writing, it is the 13th highest-grossing animated film in history.

4. Star Wars: Episode III - Revenge of the Sith (2005)

If you wanna get all technical about it, the 2005 blockbuster period kicked off with Ridley Scott's Kingdom of Heaven. The lukewarm box office reception to Scott's feature, however, meant things didn't really spark to life until lightsabers were ignited with Revenge of the Sith, George Lucas' final entry in his Star Wars prequel trilogy. Often regarded as the best of the prequel saga, Episode III checks off the Star Wars boxes: thrilling space battles, tense lightsaber duels, and the birth of the greatest villain in pop culture history — Darth Vader.

Despite the tragic fall of the Jedi Order, the galactic adventure still managed to bring in almost $900 million worldwide. Now, almost two decades later, fans will get to explore the fallout of Order 66 in the Obi-Wan Kenobi series coming to Disney+.

5. Mission: Impossible III (2006)

When Mission: Impossible III (or M:i-III) came out, six long years had passed between this installment and Ethan Hunt's previous mission, the John Woo-directed Mission: Impossible II. The Tom Cruise-led franchise needed a boost and J.J. Abrams chose to accept this mission (even though his star's career was on the verge of self-destructing in five seconds, or however long it took for Cruise to jump on Oprah's couch.)

The co-creator of Felicity and Lost made the jump to the big screen with a heart-thumping feature directorial debut, one that shifted the paradigm of the series for years to come. Tom Cruise's Ethan Hunt was no longer a lone wolf — he now had a wife and would do anything to protect her. This emotional throughline would be carried on through the subsequent chapters, until being finally resolved in 2018's Fallout.

But that was a lifetime away. For now, Ethan had to get his hands on a MacGuffin called the Rabbit's Foot (What does it do? Not important!) before the calculating villain can kill his bride. As per usual, Cruise gives it his charismatic all, but it's the late great Philip Seymour Hoffman who steals the show as baddie, Owen Davian.

6. Spider-Man 3 (2007)

Yes, we know this is considered to be the weakest outing of the Raimi era, but at the time, the hype for a third Spider-Man film was through the roof. That audience anticipation manifested itself in the form of almost $900 million worldwide — the highest box office gross of the Maguire-fronted movies. How could Raimi & Co. top the near-masterpiece that was Spider-Man 2? Well, it turns out they couldn't.

This third chapter was a little too over-stuffed for its own good. Too many villains, too many storylines, and too many retcons. Still, there's plenty to like here, including the threequel's treasure trove of internet memes.

7. Iron Man (2008)

The dawn of a new superhero movie era. The birth of the Marvel Cinematic Universe. Of course, no one — not even the talented Kevin Feige — could predict what was to come over the next decade and change.

In 2008, Jon Favreau was known for directing family-friendly titles like the holiday hit Elf and the underwhelming and underrated Zathura. Quality movies with strong fan followings, but not exactly the billion-dollar franchises now entrusted to him. Favreau, however, was only one part of the gambit. The real wild card in the equation was the casting of Robert Downey, Jr., a seemingly past-his-prime celebrity with a known criminal record.

It's almost laughable in hindsight. The stars perfectly aligned on Iron Man, simultaneously breathing new life into the superhero genre on the big screen, while transforming Favreau and Downey into some of the most in-demand and influential players in Hollywood. Downey's cocksure and idiosyncratic portrayal of Tony Stark proved that no one — not even Tom Cruise, who once considered playing the role — was capable of walking in the shoes of this character who, until 2008, was not a household name. Downey was born to play Stark/Iron Man, who would launche a thousand ships, or, in this case, a cinematic universe inspired by Marvel Comics.

8. Star Trek (2009)

While X-Men Origins: Wolverine was technically the first blockbuster out of the gate that season, the tepid reaction from fans and critics alike doesn't exactly place it on anyone's “Best Of” lists.

The summer moviegoing extravaganza really kicked into high gear one week later, when J.J. Abrams' Star Trek reboot beamed onto the big screen. Abrams had a lot to prove with his second time as a movie director. Sure, Mission: Impossible had also been an established film franchise based on a classic TV series from the 1960s, but it didn't have nearly the same rabid fan base as Gene Roddenberry's magnum opus. There was no room for failure here and thankfully, Abrams did not disappoint. He boldly took Starfleet in a fresh new direction, yet still remained true to what made Trek so popular in the first place.

9. Iron Man 2 (2010)

Like Spider-Man 3, the second Iron Man film was expected to be a slam dunk. That wasn't exactly the case (at least from an audience perspective) but come on — $128 million in opening domestic sales alone isn't something to shake a stick at.

For all its faults, Iron Man 2 is still a lot of fun, especially when Sam Rockwell is doing his thing as Justin Hammer. In fact, he probably should have been the sole villain of the movie (this video does a great job of explaining why). The best, of course, was still to come. It was still early days for the MCU, with the origin movies for Thor and Captain America still a year away.

10. Thor (2011)

"Shakespeare, but make it in space." That's the basic conceit of the initial chapter in the Thor franchise directed bu Kenneth Branagh, a movie that was set up by the post-credits scene in Iron Man 2. Hard to believe Chris Hemsworth and Tom Hiddleston were virtual unknowns back then. The Asgardian God of Thunder probably didn't start out as anyone's favorite character, but time makes fools of us all. Once Taika Waititi's Thor: Love and Thunder opens this summer, Thor will be the only MCU hero to have four standalone adventures.

11. The Avengers (2012)

The first Avengers movie proved that Kevin Feige wasn't a madman. The grand experiment of a shared cinematic universe inspired by the Marvel library could have backfired horribly, but it didn't. A crossover adventure with Iron Man, Captain America, Thor, Hulk, Black Widow, and Hawkeye paid off big-time to the tune of more than $1 billion in worldwide ticket sales. And thus, the very nature of the blockbuster began to evolve as Hollywood tried (and in most cases, failed) to emulate the Feige magic.

12. Iron Man 3 (2013)

Jon Favreau decided to abdicate the director's chair for Iron Man 3, ceding the creative reigns over to Shane Black, who had previously worked with Downey on Kiss Kiss, Bang Bang. While the end product didn't live up to the bar of excellence set by the 2008 original, the money — another billion in Marvel's pocket — rolled in like there was no tomorrow.

Black's unique style of comedy and trademark love of the Christmas seasons makes for an enjoyable romp in which Tony grapples with the PTSD of what went down during The Battle of New York. The whole “Mandarin” subplot was a bit ill-advised, but at least it got fixed in Shang-Chi and the Legend of the Ten Rings.

13. X-Men: Days of Future Past (2014)

Inspired by the indelible comic book storyline of the same name from Chris Claremont and John Byrne, X-Men: Days of Future Past expertly married the original X-Men films' timeline with Matthew Vaughn's First Class. When killer robots known as Sentinels start hunting down mutants (and anyone suspected of passing on the X-Gene), Logan is sent back in time to prevent the dystopian, Terminator-esque future from ever taking place. The ‘70s-set portion of the narrative is a groovy blast while the future scenes (in which our surviving heroes make a last stand against the Sentinels) constantly looms in the background, reminding us of what's at stake. Evan Peters gives the obvious standout performance here as Pietro Maximoff/Quicksilver, who — kind of, sort of — popped up in the MCU via WandaVision on Disney+.

14. Avengers: Age of Ultron (2015)

From here on out, it's all Marvel Studios, all the time, baby!

Age of Ultron, the penultimate chapter in Phase 2 of the MCU, represented a major turning point for the franchise, which cemented its status as a mainstay of the blockbuster summer season. No crop of summer movies was complete without a Marvel project somewhere in the mix. That hasn't changed in the seven years since Age of Ultron first hit theaters. Ambitious to a fault, the sophomore Avengers title raised the scope of what was possible with these types of movies. For better or worse, this upping of the ante conditioned audiences to expect something a little bigger each time.

15. Captain America: Civil War (2016)

Yeah, we know the title says “Captain America,” but this is really Avengers 2.5. The introductory chapter of Phase 3 marked the second MCU effort from a pair of up-and-coming directors by the names of Joe and Anthony Russo. Before their stint on The Winter Soldier in 2014, the sibling filmmakers were known for episodes of television — mainly fan favorite comedies like Arrested Development and Community. Who would have guessed that their small experience would translate so well into the world of blockbusters?

Civil War had a lot of heavy lifting to do. Not only did it have to delve into the massive fallout of The Winter Soldier and Age of Ultron, but it also had to introduce a number of fresh faces, including Chadwick Boseman's Black Panther and a brand-new iteration of Spider-Man, played by a still-unknown Tom Holland. This landmark partnership between Disney and Sony was unheard of at the time, but showed the ever-growing influence of the Mouse House's Marvel banner.

16. Guardians of the Galaxy Vol. 2 (2017)

To talk about the MCU is to talk about risk. We keep bringing up that word because Marvel Studios didn't always have access to A-list characters like Spider-Man and the Fantastic Four. Because of that, they had to get creative — they had to scrape the bottom of the barrel and perform some sort of alchemical magic that turned D-list properties into billion-dollar franchises.

In 2014, the Guardians of the Galaxy were as much of an unknown quantity as writer-director James Gunn. What a difference three years can make! Fast forward to 2017 and Guardians of the Galaxy Vol. 2 was must-watch viewing for anyone looking to start their summer off on the right foot. Audiences yearned to revisit Gunn's ragtag collection of cosmic heroes while, at the same time, jamming out to another curated soundtrack of retro hits. The Guardians went from relative obscurity to $800 million in less than a month.

17. Avengers: Infinity War (2018)

By the time Avengers: Infinity War rolled around, Marvel Studios wanted to flex on all of us. The April 27 release date was their way of saying, “We'll tell you when summer starts.”

A decade after the first Iron Man arrived on the scene, the MCU faced its biggest challenge yet: An epic culmination of then-18 feature films. Again, the house of cards might have toppled under the weight of its own lofty aspirations, but $2 billion at the global box office doesn't lie. The first part in the grand struggle against Josh Brolin's Infinity Gauntlet-wielding Thanos perfectly encapsulated what the blockbuster season is all about: enticing moviegoers to line up around the block for a one-of-a-kind cinematic event.

The exhilaration of seeing Rocket Raccoon trying to buy Bucky's arm on a Wakandan battlefield is something you won't find anywhere else. Most of us probably felt like Ian Malcolm seeing the dinosaurs in Jurassic Park for the first time: “You did it. You crazy son of a b***, you did it.” Joe and Anthony Russo pulled it off with style and kudos to Feige for having the cojones to include the Empire Strikes Back downer of an ending where the villain actually wins.

18. Avengers: Endgame (2019)

It's feels a bit weird call Infinity War an appetizer for the main course, but the three-hour Endgame really does make it look like a cocktail hour canapé by comparison.

The mystery of how the Avengers would reverse the now-infamous Snap stewed in our minds for an entire year, leading to the kind of audience excitement you can't buy with all the money in the world. Sending our heroes on a time travel "heist" to collect the Infinity Stones and restore half of all life in the universe was the best choice the filmmakers could have made. This almost meta retrospective served as a wonderful reminder of everything the MCU had accomplished up that point.

Endgame proved why slow and steady wins the race — why every other studio attempt at a cinematic universe had crashed and burned. This was 11 years of well-earned build-up, of getting to know these characters through several world-building blockbusters. So that when Captain America summons Mjolnir and utters those two magical words — "Avengers...assemble" — the moment carries real weight. Three years and one pandemic later, we've still got chills. This video proves our point nicely.

We forgetting anything? Oh, yeah! Endgame was also the highest-grossing movie in history — at least for a brief period of time before Avatar snatched the crown back up.

19. Black Widow (2021)

Black Widow is small potatoes when compared to the likes of Infinity War and Endgame. And that's by design; it was intended to provide a proper sendoff for a character who gave up her life to save the universe. Originally meant to be the start of Phase 4, the standalone project explores Natasha's backstory and reveals what sort of hijinks she got up to between the end of Civil War and the start of Infinity War.

Had it originally opened in May 2020 like it was supposed to, Black Widow may have come and gone with very little fanfare. In the end, the movie opened in the summer of 2021, more than a year after the COVID-19 pandemic ravaged Hollywood and exhibitors alike. To those of who crave the theatrical experience, it was a godsend. Between theatrical and Disney+ Premier Access sales, the movie set a new pandemic record of $215 million.