Before Tom Holland took up the mantle as Peter Parker for the MCU, both prior live-action Spider-Men had come up against Harry Osborn during their respective franchises, with James Franco playing the character during Sam Raimi's trilogy of movies and Dane DeHaan taking on the role in 2014's The Amazing Spider-Man 2.

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Updated on January 24th, 2022 by Mark Birrell: With Spider-Man: No Way Home proving that there's room enough for more than one live-action Spider-Man, not to mention a host of live-action villains cohabitating the same movie, it raises the question of whether fans will be seeing the return of Harry Osborn any time soon.

Willem Dafoe's Norman Osborn has already returned for the MCU, so could a version of James Franco's Harry Osborn be close behind? Similarly, fans seem more ready for an Amazing Spider-Man 3 to come to fruition than ever, so could Dane DeHaan's Green Goblin get a chance to finish their arc? Which would be more deserving? Let's look at the best qualities of each iteration of the iconic character. 

Dane DeHaan Was The Best Harry Osborn Because

He Looked Awesome In The Goblin Suit

Dane DeHaan as The Green Goblin in The Amazing Spider-Man 2

Not everybody was a fan of the way DeHaan's Harry looked as the Green Goblin in The Amazing Spider-Man 2. Instead of donning green armor and a purple hat like in the comics, he instead more literally resembled a goblin because of a degenerative disease called "Retroviral Hypodysplasia", which Harry inherits from his father.

However, it was a fresh and unique take on the character. DeHaan looked frightening in a monstrous way, and the detail in the more prototype-looking suit means that there are always interesting things that fans can notice upon re-watching.

He Oozed Villainy

Harry Osborn walking through NYC in The Amazing Spider-Man 2

Given that The Amazing Spider-Man 2 was released just seven years after Spider-Man 3, fans wanted something different from DeHaan's Harry and he's the exact opposite to what Goblin Jr. was during Raimi's trilogy, oozing villainy even before undergoing a drastic transformation.

He wastes no time laying down the law to board members at Oscorp. Harry is ruthless as he sets about making his mark and is desperate enough to kill–or stand by while Electro kills for him–long before getting on the glider. Changing physically was just the last piece of the Goblin jigsaw in this version of Peter Parker's story.

He Had Good Chemistry With Other Bad Guys

Harry Osborn and Electro talking in The Amazing Spider-Man 2

Everyone loves a good villain team-up and fans got plenty of that in The Amazing Spider-Man 2. Harry's story runs in tandem with Electro's, with the pair teaming up about halfway through the movie.

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DeHaan also had good chemistry with Chris Cooper, who played Norman, and the mysterious Gustav Fiers, who implies that Harry would lie at the center of a Sinister Six team-up in the franchise's future before Spider-Man entered the MCU and plans changed once again.

There Was More Story To Tell

The Vulture and Doc Ock suits in The in Amazing Spider-Man 2.

The arc of James Franco's Harry Osborn was definitely finished by the time of his death in Spider-Man 3 but the same can't be said for Dane DeHaan's.

With Harry not featuring in The Amazing Spider-Man, his appearance in the sequel was meant to be the start of a long story. He'd already teamed up with Electro, and The Amazing Spider-Man 2 ended with him instructing Gustav Fiers to enlist the Rhino, while hints were dropped that Vulture and Doctor Octopus would be appearing further down the line. Talk of a Sinister Six movie has never really gone away and fans seem as excited about the prospect now as they did back in 2014.

He Had A Killer Instinct

Gwen Stacys Death in The Amazing Spider-Man

While Norman and Harry Osborn are both villainous in the Sam Raimi trilogy, Dane DeHaan's Harry Osborn is pure evil once he transforms into the Green Goblin in The Amazing Spider-Man 2. He doesn't just go after Peter's love interest, he actually succeeds in killing her.

Gwen Stacy's death was somewhat inevitable given that this aspect of her character is what most fans know and expect, but by making Harry Osborn the one who's directly responsible, it flipped the tables of the rivalry between Harry and Peter in the Raimi sequels, where Spider-Man kills someone that Harry loves. It was a great setup for more intense drama down the road.

James Franco Was The Best Harry Osborn Because

He Was Easy To Sympathize With

Norman Osborn telling Harry to avenge him Spider-man 2

The Amazing Spider-Man 2 shows very little interaction between Norman and Harry Osborn before Norman's sudden death and it's possible that, like with J. Jonah Jameson, this is because the producers knew that this was one aspect of the Raimi films that was unlikely to be topped.

Norman is such a cold and intimidating presence in Harry's life in Raimi's original Spider-Man movies that it's hard not to feel a little sorry for him. But it's Franco's performance as Harry that really taps into the more pathetic side of the character, making the audience feel the pain and humiliation of his weaknesses and overall childishness.

His Arc Was Well-Planned

Harry Osborn preparing to stab Peter in Spider-man 2

Dane DeHaan starts off at the beginning of The Amazing Spider-Man 2 as Harry before changing into the villain everyone knows and loves but Franco's Harry Osborn had his turn to villainy played out over several movies in the Raimi trilogy.

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It was carefully planned and took its time. For the bulk of the first two movies, Franco's version of the character gets increasingly angry and disillusioned with the world. When he comes across his father's old armor at the end of Spider-Man 2, it was one of the best sequel set-ups that comic book movie fans had ever seen.

His Chemistry With Tobey Maguire Was Brilliant

James Franco and Tobey Maguire in Spider-Man

While Dane DeHaan had superb chemistry with villains such as Electro, Norman Osborn, and Gustav Fiers, Franco had a superb on-screen relationship with Maguire during the Raimi trilogy. They were believable as polarized best friends during the first movie, their hostility arising made sense in the second, and there was definitely an air of tragedy before Harry's death in the third.

The character's death brought a huge amount of closure to the end of the movie, helping Raimi's 3 films stand up as a complete trilogy as opposed to a franchise that ended too early due to insurmountable creative differences, which some fans also view them as.

He Had Awesome Gadgets

harry osborn on his new glider in Spider-man 3

Norman Osborn had some pretty incredible gear when was the Green Goblin and Harry inherits all of this in Spider-Man 2 before putting them to use in the following movie. He's got pumpkin bombs, a snowboard-like glider, and a sword that comes precariously close to cutting Peter in half when they face off.

If anything, it was too powerful. Harry actually dies because of his own equipment. Venom picks up his glider when he's knocked off it and, as he aims to kill Peter, he drives it through the New Goblin instead. This echoes what happened with Norman, who accidentally stabs himself in the first installment of the Raimi trilogy.

He Was Slicker And Cooler

James Franco as Harry Osborn in Spider-Man 3

As a son of a millionaire, Harry is meant to be rather arrogant and confident. Franco nails this, especially in Spider-Man 2 when he's head of Oscorp and relishing the chance to work with Doctor Octavius, who is poised to make him a significant amount of money.

Harry walks with a swagger, wearing nice suits and giving off a huge air of confidence. It's the same in Spider-Man 3 when his memory returns, with the New Goblin loving the chance to meddle in Peter and Mary Jane's relationship, forcing the pair to break up. He actually seems happier when his father dies, but that doesn't stop him from following in his villainous footsteps further down the line.

NEXT: Ranking Every Villain In Sam Raimi's Spider-Man Trilogy