Spider-Man Stars Then & Now: See Tobey Maguire, Tom Holland, Andrew Garfield, & More From Their First Movie To Today

By:

Elissa Anderson

December 16, 2021 11:45PM EST

‘Spider-Man: No Way Home’ is topping the box office and thrilling fans. As one of the comic world’s most iconic characters, it’s no surprise that Spider-Man has spawned a slate of blockbuster movies. Let’s see the cast and characters who’ve graced the Spider-Man films over the last two decades!

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Spider-Man Stars Through The Years

Spider-Man Stars Through The Years — ‘Spider-Man: No Way Home’ secured its place in movie history when it swung onto the screens on Dec. 17 2021. The Marvel movie — which stars Tom Holland and Zendaya — had the 2nd best opening day ever, raking in $121 million at US box offices, according to Deadline. It ranks behind fellow MCU flick ‘Avengers: Endgame’ ($157.4M) and ahead of ‘Star Wars: The Force Awakens’ ($119.1M). And Spidey is on track for a monumental weekend, set to earn an estimated $242 million to $247.5 million over the 3-day stretch.

It’s no wonder why ‘Spider-Man: No Way Home’ has come out on top. As one of the comic world’s most iconic characters, the superhero has spawned a slate of blockbuster movies. Though the casts and plotlines have changed through the years, Spider-Man’s red and blue suit and super-human senses have stood the test of time.

Though there were several TV versions of Spider-Man in the 70s and 80s, it wouldn’t be until 2002 that the film hit the Hollywood big-screen with ‘Spider-Man’ starring Tobey Maguire. He would lead 3 films.

Andrew Garfield took on the role in ‘The Amazing Spider-Man’ movies in 2012 and 2014, portraying a comedically charming version of the super-hero. Tom Holland debuted a youthful Spidey in 2016’s ‘Captain America: Civil War’ opposite The Avengers. His first movie headlining as Spider-Man was 2017’s ‘Spider-Man: Homecoming’, however. His 3rd movie, ‘Spider-Man: No Way Home’, came out Dec. 17 2021.

Check out all the stars that have starred in Spider-Man through the years. Click through to see photos from 2002 to now!

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Tobey Maguire in ‘Spider-Man’

Tobey Maguire in ‘Spider-Man’ — Tobey Maguire was an instant icon after suiting up for the first ever Spider-Man movie, 2002’s ‘Spider-Man’. He would appear in 2 sequels, which each raked in hundreds of millions of dollars.

The film introduces Tobey Maguire as Peter Parker, a nerdy teen who wakes up to find he has superpowers after being bitten by a radioactive spider. When his beloved Uncle Ben is killed by criminals, he suits up as Spidey and starts to fight crime around the city. But he gets more than he bargained for when the supervillain The Green Goblin (Willem Dafoe) starts to terrorize the down, leading to a battle between justice and chaos.

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Kirsten Dunst In ‘Spider-Man’

Kirsten Dunst In ‘Spider-Man’ — Kirsten Dunst was love interest Mary Jane Watson in the original Sam Raimi-directed Spider-Man flicks.

Kirsten called Tobey the best Spider-Man in 2017 interview, where she told Marie Claire UK, “We made the best ones, so who cares? I’m like, ‘You make it all you want.'” Taking a dig at more recent Spider-Man films, she added, “They’re just milking that cow for money. It’s so obvious. You know what I mean?” She later said she’d love to appear in any future movies, however.

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James Franco & Willem Dafoe In ‘Spider-Man’

James Franco & Willem Dafoe In ‘Spider-Man’ — Willem Dafoe and James Franco were father/son duo Norman and Harry Osborn. After Norman dies while terrorizing the city as The Green Goblin, his son vows to take revenge and follows his father’s path towards madness.

Willem’s Green Goblin is returning for 2021’s ‘Spider-Man: No Way Home’. Willem said he had fun keeping the part a secret for some time, telling Variety, “Yeah, it was kind of fun laying low on this for a while, actually. Letting people speculate about where this Spider-Man series was going. So, now people are going to see it and that’s exciting.”

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Cliff Robertson & Rosemary Harris In ‘Spider-Man’

Cliff Robertson & Rosemary Harris In ‘Spider-Man’ — Cliff Robertson and Rosemary Harris appear as the original Aunt May and Uncle Ben in 2002’s ‘Spider-Man’. Ben introduces one of the movie’s most memorable lines, telling Peter “With great power comes great responsibility.”

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Alfred Molina In ‘Spider-Man 2’

Alfred Molina In ‘Spider-Man 2’ — Alfred Molina joins the team as scientist Dr. Otto Octavius in 2004’s ‘Spider-Man 2’. After he becomes fused to mechanical arms during a botched science experiment, he goes mad and Spider-Man must stop him from trying to recreate the Earth-ending experiment. He’s set to appear in 2021’s ‘Spider-Man: No Way Home’.

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Donna Murphy In ‘Spider-Man 2’

Donna Murphy In ‘Spider-Man 2’ — Donna Murphy plays Dr. Octavius beloved wife who dies in his ill-fated experiment in ‘Spider-Man 2’, driving him over the edge. The character does not appear in the comics and was invented for the film.

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Thomas Haden Church In ‘Spider-Man 3’

Thomas Haden Church In ‘Spider-Man 3’ — Thomas Haden Church played Flint Marko AKA Sandman in ‘Spider-Man 3’. The shapeshifting criminal is coming back for ‘Spider-Man: No Way Home’. Thomas Hayden Church played Flint Marko AKA Sandman in ‘Spider-Man 3’. The shapeshifting criminal is coming back for ‘Spider-Man: No Way Home’.

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J.K. Simmons In ‘Spider-Man 2’

J.K. Simmons In ‘Spider-Man 2’ — J.K. Simmons plays the bombastic Editor-In-Chief of The Daily Bugle, J. Jonah Jameson. While he dislikes Spider-Man and aims to paint him as a crazed vigilante, he’s a big fan of Peter Parker and his photography. He first appeared in the Tobey Maguire series but reprised the role in Tom Holland’s ‘Spider-Man: Far From Home’.

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Topher Grace In ‘Spider-Man 3’

Topher Grace In ‘Spider-Man 3’ — Topher Grace plays Eddie Brock in ‘Spider-Man 3’. He is introduced as Peter’s rival at the newspaper before he is taken over by an extraterrestrial which turns him into the anti-hero Venom. Venom is portrayed by Tom Hardy in MCU but has yet to make an appearance in the Tom Holland films.

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Bryce Dallas Howard In ‘Spider-Man 3’

Bryce Dallas Howard In ‘Spider-Man 3’ — Bryce Dallas Howard is introduced as Gwen Stacy in 2007’s ‘Spider-Man 3’. She is Peter’s lab partner and is the daughter of NYPD Captain George Stacy. Though Peter and Gwen click, he offends her when he takes her out dancing at the restaurant Mary Jane works, just to make his ex jealous. By the end of the movie the pair make amends.

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Andrew Garfield In ‘The Amazing Spider-Man’

Andrew Garfield In ‘The Amazing Spider-Man’ — Andrew Garfield made his first appearance in ‘The Amazing Spider-Man’ in 2012. Talking about the role with Business Insider in 2014, Andrew said, “The way I feel about Spider-Man and Peter Parker is he is a metaphor for all of our lives in the sense that we are all Peter Parker.”

“We are all ordinary, we all [have] the same imperfections and struggles. We all have flaws and we all are fallible. And we are all Spider-Man in a sense that we have something extraordinary to give. We have some superpower whether that be for heroism, whether that be for art, whether that be for creativity, whether that be for science, mathematics, athleticism.”

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Emma Stone In ‘The Amazing Spider-Man’

Emma Stone In ‘The Amazing Spider-Man’ — Emma Stone is love interest Gwen Stacy in ‘The Amazing Spider-Man’. She is the daughter of the chief police officer, George Stacy, played by Denis Leary. She would call her character the ‘opposite of a damsel in distress‘ while promoting the sequel in 2014.

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Rhys Ifans In ‘The Amazing Spider-Man’

Rhys Ifans In ‘The Amazing Spider-Man’ — Rhys Ifans is Dr. Curt Connots AKA Lizard in ‘The Amazing Spider-Man’. The brilliant Oscorp scientist is transformed into a reptilian monster that wreaks havoc on the city after meddling with lizard DNA.

Teasing a potential appearance in 2021’s ‘Spider-Man: No Way Home’, he told the site Murphy’s Multiverse, “Well, you know, like most Christmas presents, the good thing is not knowing what’s in them until it’s time to open them.”

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Denis Leary In ‘The Amazing Spider-Man’

Denis Leary In ‘The Amazing Spider-Man’ — Denis Leary plays the stern New York City police captain George Stacy. Talking about working with Andrew Garfield in 2021 with IGN, Denis said, “I love Andrew. He’s terrific in the role. He was trained as a gymnast growing up, which came in handy. Most of the stunts in the movie are done live in front of the cameras.”

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Cambell Scott In ‘The Amazing Spider-Man’

Cambell Scott In ‘The Amazing Spider-Man’ — Cambell Scott plays Peter’s dad Richard Parker in flashback scenes in ‘The Amazing Spider-Man’. Peter’s parents did not appear in the Sam Raimi series.

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Martin Sheen & Sally Field In ‘The Amazing Spider-Man’

Martin Sheen & Sally Field In ‘The Amazing Spider-Man’ — Martin Sheen and Sally Field play Aunt May and Uncle Ben in ‘The Amazing Spider-Man’ films.

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Jamie Foxx In ‘The Amazing Spider-Man 2’

Jamie Foxx In ‘The Amazing Spider-Man 2’ — Jamie Foxx is the outcast villain Matt Dillon AKA Electro in ‘The Amazing Spider-Man 2’. He becomes obsessed with Spider-Man and a subsequent accident gives him electrifying powers, which are beyond his control. In turn, Spider-Man must grapple with what it means to face someone who outpowers him. Jamie is set to return for ‘Spider-Man: No Way Home’.

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Dane DeHaan In ‘The Amazing Spider-Man 2’

Dane DeHaan In ‘The Amazing Spider-Man 2’ — Dane DeHaan plays his version of Harry Osborn in ‘The Amazin Spider-Man 2’, out in 2014. Like James Franco’s version, he goes cuckoo after injecting a special serum of spider-venom into his body.

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Embeth Davidtz At ‘The Amazing Spider-Man 2’ Premiere

Embeth Davidtz At ‘The Amazing Spider-Man 2’ Premiere — Embeth Davidtz plays Peter Parker’s mother in both of ‘The Amazing Spider-Man’ films. The South African actress is well known for her role as Miss Honey in the movie ‘Matilda’.

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Paul Giamatti In ‘The Amazing Spider-Man 2’

Paul Giamatti In ‘The Amazing Spider-Man 2’ — Paul Giamatti is the villain Rhino in ‘The Amazing Spider-Man 2’. The Russian hitman uses an armored mechanical suit and battles with Spidey. Paul said he had a blast with the character, telling the Toronto Sun in 2014, “He’s a Russian mobster. Russians are always good villains. I have an ability to just destroy things.”

“My accent is pretty hammy. I loved doing it. It seemed to me like an opportunity to be as over-the-top hammy as possible. It was really fun.”

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Tom Holland In ‘Spider-Man: Homecoming’

Tom Holland In ‘Spider-Man: Homecoming’ — ‘Spider-Man: Homecoming’ came out in July 2017 and quickly raked in over $880 million at the box office.

Tom’s version of super-teen Peter Parker was first introduced in 2016’s ‘Captain America: Civil War’, where he was recruited by Iron Man Tony Stark (Robert Downey Jr.) to join The Avengers. Tom became the leading man with 2017’s ‘Spider-Man: Homecoming.

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Michael Keaton In ‘Spider-Man: Homecoming’

Michael Keaton In ‘Spider-Man: Homecoming’ — Michael Keaton is the villain Adrian Toomes AKA Vulture in ‘Spider-Man: Homecoming’.

Michael Keaton plays Adrian Toomes AKA Vulture in 2017’s Spider-Man: Homecoming. He is a salvager-turned-arms trafficker who uses a suit with mechanical wings and has a run-in with Spider-Man after getting run out of business by Tony Stark AKA Iron Man.

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Jon Favreau, Robert Downey Jr. & Tom Holland In ‘Spider-Man: Homecoming’

Jon Favreau, Robert Downey Jr. & Tom Holland In ‘Spider-Man: Homecoming’ — Jon Favreau and Robert Downey Jr. first appear in ‘Spider-Man: Homecoming’ and return again for ‘Spider-Man: Far From Home’. RDJ is Tony Stark and Jon Favreau is Happy Hogan, head of security for Stark Industries. Billionaire Tony and young Peter form a close bond in the films.

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Zendaya In ‘Spider-Man: Homecoming’

Zendaya In ‘Spider-Man: Homecoming’ — Zendaya plays the sassy Michelle ‘MJ’ Jones in the MCU Spider-Man flicks, first making her debut in ‘Spider-Man: Homecoming’.

Zendaya talked about her connection to her character with Entertainment Weekly in 2017, saying “My character is not romantic. My character is like very dry, awkward, intellectual, and because she’s so smart, she just feels like she doesn’t need to talk to people, like, ‘My brain is so far ahead of you that you’re just not really on my level.’ So she comes off very weird. But to me, she is very cool because she’s deep.”

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Jacob Batalon & Tom Holland In ‘Spider-Man: Homecoming’

Jacob Batalon & Tom Holland In ‘Spider-Man: Homecoming’ — Jacob Batalon was a breakout star in ‘Spider-Man: Homecoming’ where he plays Peter’s devoted best friend Ned Leeds.

He was new to movies when he was cast and remembers being very ‘nervous’ ahead of the first shoots. Jacob told Variety, “I remember being very nervous and I was wearing goggles that steamed up every time I would start to sweat and that made me even more nervous. But it was amazing.”

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Laura Harrier In ‘Spider-Man: Homecoming’

Laura Harrier In ‘Spider-Man: Homecoming’ — Laura Harrier appeared as Liz in ‘Spider-Man: Homecoming’. Her character is one of Peter’s high-achieving classmates, who just happens to be the daughter of nemesis Vulture.

Laura intially thought she lost out on the role for Zendaya, only later to learn they were going for different parts. She told Net-A-Porter, “After I did my screen test for Spiderman, before I had heard anything, it came out a few weeks later that Zendaya was going to be cast in it, so I just figured I hadn’t got the job. She must have.”

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‘Bokeem Woodbine In ‘Spider-Man: Homecoming’

‘Bokeem Woodbine In ‘Spider-Man: Homecoming’ — Bokeem Woodbine played Herman Schultz AKA Shocker in ‘Spider-Man: Homecoming’. His character is one of Vulture’s accomplices who uses super-weapons to fight.

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Spider-Man Stars Through The Years

Spider-Man Stars Through The Years — Marisa Tomei started her run as Aunt May in ‘Spider-Man: Homecoming’. Though the part was originally drawn as a much older woman, Marisa earned the part at age 54.

Talking about her casting years later, she told The New York Times in 2017, admitting she was “horrified” when she learned more about how the character was depicted in the comics and past movies. “Talk about crushed… They just kept saying ‘an iconic character, an iconic character.’… I was more focused on my deal, honestly. And then, the illustration was revealed to me.”

She added, “There’s nothing wrong with that depiction of the character. I don’t want to be coming from an ageist point of view about that, at all. It was my own personal cross to bear at that moment. But in the scope of things, why not?”

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Shameik Moore, Hailee Steinfeld And More Voice Characters in ‘Spider-Man: Into The Spider-Verse’

Shameik Moore, Hailee Steinfeld And More Voice Characters in ‘Spider-Man: Into The Spider-Verse’ — The computer-animated feature ‘Spider-Man: Into The Spider-Verse’ introduced multiple versions of Spidey. In the photo, there is Peni (Kimiko Glenn), Spider-Gwen (Hailee Steinfeld), Spider-Ham (John Mulaney), Miles Morales (Shameik Moore), Peter Parker (Jake Johnson), and Spider-Man Noir (Nicolas Cage).

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Jake Gyllenhaal & Tom Holland In ‘Spider-Man: Far From Home’

Jake Gyllenhaal & Tom Holland In ‘Spider-Man: Far From Home’ — Jake Gyllenhaal was introduced as hero Mysterio in ‘Spider-Man: Far From Home’. His character would turn out to be just Quentin Beck, a former Stark Industries employee and holographic-illusions specialist with a grudge against his former employer.

Jake said he was fascinated by the idea of playing a master manipulator, telling The Hollywood Reporter in 2019, “What I love about Mysterio is that he has so many different faces.” He continued, “You could play someone who literally calls themself Chameleon, or you could play somebody who says that they’re a bad guy, but this is somebody who exists on either side of the line all the time.

“That way, he’s utter confusion, and in that way, he’s sort of unbeatable, which makes him almost un-actable. Because of that, I thought that would make a great challenge. I don’t know if I have an aversion to the more well-known characters; I don’t. It’s just that he presented me with a Rubik’s Cube, and I loved that.”

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Tony Revolori At ‘Spider-Man: Far From Home’ Premiere

Tony Revolori At ‘Spider-Man: Far From Home’ Premiere — Tony Revolori was introduced as Eugene ‘Flash’ Thompson in the first MCU Spider-Man movie, ‘Homecoming’. Though the character was depicted as a bully in the comics, he is more of Peter’s rival in the movies. Talking about the dynamic, Tony said “One of the reasons he doesn’t like Peter. Everyone else seems to like Peter, so he’s like, why don’t they like me like they like him?”

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Cobie Smulders & Samuel L. Jackson In ‘Spider-Man: Far From Home’

Cobie Smulders & Samuel L. Jackson In ‘Spider-Man: Far From Home’ — Cobie Smulders and Samuel L. Jackson reprise their Avengers roles as S.H.E.I.L.D. secret agents Maria Hill and Nick Fury.

Director Jon Watts talked about Nick’s relationship with young Spidey in a 2019 chat with USA Today, saying, “If Tony is like the supportive cool uncle, Fury’s more like the mean new stepdad.”

“Fury doesn’t see himself in Peter Parker,” he said. “Fury sees Peter Parker as an asset that he needs who is too preoccupied with a bunch of high school problems. Part of my pitch for the very first movie was bringing Nick Fury in and making him the mean substitute teacher.”

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J.B. Smoove At ‘Spider-Man: Far From Home’ Premiere

J.B. Smoove At ‘Spider-Man: Far From Home’ Premiere — J.B. Smoove plays Peter’s teacher Julius Dell in ‘Spider-Man: Far From Home’. He’s set to appear again in ‘Spider-Man: No Way Home’.

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Martin Starr At ‘Spider-Man: Homecoming’ Premiere

Martin Starr At ‘Spider-Man: Homecoming’ Premiere — Martin Starr is science teacher Roger Harrington in the Marvel Cinematic Universe. In addition to appearing in the Spider-Man films, he is also featured in The Incredible Hulk with Mark Ruffalo.

Talking about the movie with ComicBook.com in 2017 ahead of ‘Homecoming’, the ‘Silicon Valley’ star said, “It’s capitalizing on popularity and a story that’s very rich and dense, so there’s a lot left to tell.”

“And this isn’t a familiar take on it — this is a unique kind of take of a younger Spider-Man trying to figure out life again. The story has a lot of action and fun in it, but it’s also a sweet, coming-of-age story of a kid.”

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Tom Holland In ‘Spider-Man: No Way Home’

Tom Holland In ‘Spider-Man: No Way Home’ — Tom is back again as Spidey in ‘Spider-Man: No Way Home’. Former Spider-Guys Tobey Maguire and Andrew Garfield are reportedly back in action for the MCU flick, where alternate timelines converge after some messy magic by Dr. Stephen Strange (Benedict Cumberbatch).

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