Spider-Man's Tangled Romantic Web, From Kirsten Dunst To Emma Stone

With Stone set to play Spidey's girlfriend Gwen Stacy in the upcoming reboot, we look back at the cinematic superhero's complicated love life.

Over the course of three big-screen installments of "Spider-Man," Peter Parker has struggled almost as much with his love life as he has with chemically altered goblins and evil alien goo. The fourth take on the tights-wearing wonder-boy — a franchise reboot featuring Andrew Garfield as the new Spidey — has not publicly settled on its villain of choice, but now we know at least one of the women who will tie the acrobatic superhero's romantic web in knots: Emma Stone, who will play Gwen Stacy.

Sony Pictures announced Tuesday that Stone ("Superbad," "Zombieland") had won the coveted starring role. Previous reports suggested the 21-year-old actress would play Mary Jane Watson, a central love interest previously depicted by Kirsten Dunst. Stacy initially popped up in "Spider-Man 3," with Bryce Dallas Howard portraying Parker's doomed first love.

Could Watson also make an appearance in the new "Spider-Man"? And what would any attempt at balancing two lovely young women do to our friendly neighborhood hero? At least the guy has had some practice in the art — and the war — of love.

"Spider-Man" (2002)

When we first found Parker, then played by Tobey Maguire, he was just a four-eyed science geek with a serious crush on his next-door neighbor Watson. Mary Jane, alas, had the hots for Parker's buddy, the strapping Harry Osborn (James Franco). But one genetically altered spider bite later and Parker was suddenly coming to Watson's rescue after she nearly took a spill in the school cafeteria.

Spidey soon graduated to other heroically romantic acts, like attempting to win a wrestling tournament and earn enough cash to buy a make-Mary-Jane-go-gaga sports car. Eventually, he saves her life when the Green Goblin stirs up fiery trouble. These amorous gestures work, and Mary Jane falls hard for Parker's alter ego — just not Parker himself. It's as Spidey, after all, that Parker gets to enjoy that iconic upside-down kiss with Mary Jane.

But by film's end, in a neat bit of magical movie plotting, Mary Jane ends up confessing her love for Parker. Score! Only problem is Peter is worried that being in a relationship with Mary Jane would be too dangerous for her. Relationship interrupted. The flick ends on an ambiguous note: Does she finally realize who Spider-Man really is?

"Spider-Man 2" (2004)

The sequel begins with Parker out of contact with Mary Jane, who went off and became a successful Broadway actress and is engaged to an astronaut named John Jameson. Yet she can't forget about Peter.

"I can't keep thinking about you," she says. Nor can Peter stop thinking about her, even if he can't carve out enough free time from his evil-fighting duties to go and see her show. Men! Enough is enough, he decides, giving up being Spider-Man and devoting himself to activities of a more lovey-dovey variety. Awww. That works for a little while, until a mechanical-arm-assisted baddie named Doc Ock shows up and kidnaps Mary Jane to use as bait to lure in Spidey.

It's then that Mary Jane finally sees Spider-Man without a mask on: She now knows the truth. Not that the truth helps their shot at love. As he had in the original flick, Parker decides it's too risky to settle down with Mary Jane. She then basically says, "To hell with that," ditching out on her wedding and running off in her white gown to smooch Peter. No sooner do they lock lips, though, than Parker is called away to help in some unknown emergency.

"Go get 'em, tiger!" Mary Jane says.

"Spider-Man 3" (2007)

To start off this third installment, the boy wonder is at the top of his game: Spidey's beloved by all, and Parker is getting set to ask Mary Jane to be his wife. All this doesn't last very long. A meteorite unleashes an alien symbiote that infuses Peter with a decidedly more aggressive personality. Not cool.

"Do you want to push me away?" she asks him at one point and goes off to seek comfort with Harry, who eventually convinces Mary Jane to dump Peter. Enraged with jealousy, Peter takes Gwen Stacy, whose life he has saved, on a date at the club where Mary Jane waits tables. A fight ensues. Nice plan, dude!

Cut to the villains Sandman (Thomas Haden Church) and Venom (Topher Grace) joining forces to defeat Spidey, which leads to Mary Jane being kidnapped and trapped high in the air in a taxi cab. But wouldn't you know it? Our hero dusts himself off and comes to her rescue. Later, Peter finds Mary Jane singing in a nightclub. They reach out their hands for each other. They embrace as the camera spins around them. All is well, at least for now.

Which Spidey love interest is your favorite? Let us know in the comments!

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