With talk rife that Toby Maguire will be reprising his role when Spider-Man: No Way Home hits theatres at the end of the year, it's a good time to look back at the three movies starring the actor. Sam Raimi's trilogy was a huge success, with the first installment releasing in 2002. Spider-Man 2 then followed two years later, with the divisive Spider-Man 3 bringing things to a close in the summer of 2007 - trumping many hits at the box office.

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Over the course of the trilogy, many brilliant characters were introduced. However, some worked better on screen than others when paired with one of the other cast members.

Worked: Peter And Mary Jane

Peter Parker and Mary Jane Watson talk in Spider-Man 2

Starting with the obvious, it's Peter Parker and Mary Jane Watson. Sure, their dialogue in 2002's Spider-Man can definitely be a little cringy at times but, after they finally coupled up in the sequel, they're believable as an item.

One complaint is that Mary Jane had a really passive role, often relying on Peter to save her from some kind of supervillain. But Maguire and Kirsten Dunst's chemistry was excellent, with the duo arguably the two most important characters in the entire franchise. Dunst, like Maguire, is rumored to appear in No Way Home as well - and that's likely to spark quite the reaction.

Didn't Work: Peter And Gwen Stacy

Peter and Gwen dance Spider-Man 3

For Spider-Man 3, the decision was made to make Peter an unofficial fourth villain after he encounters the Symbiote. And during this time where the web-slinger is skating along the thin line of good and bad, he begins a relationship with Bryce Dallas Howard's Gwen Stacy.

Yet while Peter is merely using Gwen to make Mary Jane jealous after their break-up, their date at the jazz club is corny to see play out. Maguire dances cringingly and Gwen is left heartbroken when the truth finally dawns on her. They had precious little backstory beforehand and the date seemed a way to further the plot, rather than having any significant impact on things.

Worked: Peter And Harry

James Franco as Harry Osborn in Spider-Man 3

James Franco was cast in the role of Harry Osborn for all three movies of the Raimi trilogy. And, like with Dunst, his chemistry with Maguire's version of Peter Parker is bang on the money. They're believable as friends in the first movie, frenemies in the second, and outright enemies in the third.

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This makes the death of Harry at the end of Spider-Man 3 all the more heartbreaking given all he's gone through with Peter and Mary Jane, with Franco's character meeting his end when he's impaled by Venom with his own glider. This eerily echoes the fate of his father, Norman Osborn, who perishes in similar circumstances during the 2002 blockbuster.

Didn't Work: Harry And Mary Jane

Mary Jane and Harry Osbourn

In the first Spider-Man movie, Harry Osborn and Mary Jane Watson start dating. But this is a rather surprising development given how things between the pair initially start out.

Mary Jane is evidently uninterested as Harry relays facts about spiders to her during a field trip - yet that didn't stop Raimi from putting them together later on. Again, this was a decision that felt forced. And their brief reconciliation in Spider-Man 3 is pretty bizarre, too, given Mary Jane is still in love with Peter at this point. The kiss may have been dramatic to watch but, all things considered, it was another problematic subplot of the film.

Worked: Norman Osborn And Harry Osborn

Norman Osborn with a creepy smile in Spider-Man, grinning evilly

Part of what makes Norman Osborn such a fantastic villain is his need for control. He can't stand the prospect of Oscorp falling apart, which is why he takes the Green Goblin formula: to maintain the power position. And it's a similar story with his son Harry, who he emotionally manipulates both before and after his death.

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Norman is believable as the pushy parent, tugging at his son's emotional heartstrings to get him to do his bidding. And Harry is certainly believable as the son too weak to stand up for himself. Norman is actually inadvertently responsible for his own son's death because, if he hadn't disclosed the truth about his Green Goblin past, Harry would likely have discovered the nasty secret hiding behind the mirror in the Osborn mansion.

Didn't Work: Mr Ditkovitch and Ursula Ditkovich

Mr Ditkovich in Spider-Man 2

Spider-Man 2 introduced the characters of Mr. Ditkovich and Ursula Ditkovich, played by Elya Baskin and Mageina Tovah respectively. But while they're nice enough, they seem as though they're only in the movie to hammer home just how downtrodden Peter is at that moment in time.

All Mr. Ditkovich does is moan about his rent, and Ursula is there at a time where the web-slinger is being rejected by both Mary Jane and Harry. In short, they're filler characters. And Sony could easily have had Peter come across as equally down in the dumps without them being involved - even if they do provide some light relief at times, to their credit.

Worked: Aunt May And Uncle Ben

Aunt May and Uncle Ben in Spider-Man

While they're only a couple during the first Spider-Man movie, Rosemary Harris and Cliff Robertson both did well in the roles of Aunt May and Uncle Ben respectively. As Peter's guardians, they had to come across as warm, affectionate, and innocent. And both actors ticked all three boxes, giving iconic performances during that movie - with Harris doing the same in the two sequels.

May is genuinely sweet and caring, always looking to help Peter even when she's struggling to help herself. And Ben is the same, offering to give Peter a lift home on the night of his tragic death. Speaking of which, there is a grievance many fans have...

Didn't Work: Sandman And Denis Caradine

Thomas Haden Church as Sandman in Spider-Man 3

The first Spider-Man movie definitely suggested Denis Caradine was solely responsible for Ben's murder. Fans see him rob the boxing promoter, steal Ben's car and even try to kill Peter when he swings in to get his revenge. However, somewhat bizarrely, Ben's death was tweaked for Spider-Man 3.

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In that movie, it's claimed Flint Marko AKA Sandman was actually responsible for the act - instead of Caradine. This ultimately undid something that had been out in the open for five years and backfired, because it seemed a cheap way of giving Marko a significant backstory. His name hadn't even been mentioned before and this was a choice that left plenty to be desired.

Worked: J. Jonah Jameson And Robbie

J Jonah Jameson - JK Simmons

As far as casting choices go, JK Simmons as J. Jonah Jameson has to rank up there with the very best. He's excellent as the head of the Daily Bugle, regularly venting his fury at Spider-Man's antics - just like in the source material.

And Robbie Robertson is excellently brought to the big screen by Bill Nunn, too. He's the perfect foil for Jameson, being the voice of calm and reason while Simmons' character flies off the handle. Newspaper editors can be pretty fierce but Robbie is always soft and appears to know Peter is Spider-Man. Conveniently, however, he fails to reveal these suspicions to anybody else.

Didn't Work: Venom And Sandman

Spidey Venom harry sandman

Sandman makes the list a second time, with his alliance with Venom not as spectacular as Sony had hoped. For most of Spider-Man 3, they don't interact with each other. But, near the end, they decide to team up to try and take Spider-Man out of the picture.

Venom has a motive, sure, but Flint Marko doesn't really. Sure, he'd been beaten to a pulp by the web-slinger earlier on but his priority is meant to be getting money to help his ill daughter, Penny. Marko appears to forget this and that undoes plenty of good things about the character, with the villain instead preferring the idea of engaging in a dangerous fight to helping the person he loves most. This doesn't make much sense at all, so that's why it makes the cut.

NEXT: Spider-Man 2: 10 Ways Sam Raimi's Sequel Is The Definitive Spidey Movie