It can be hard to decide which Spider-Man had the most emotional scenes in their respective movies. After his appearance in Spider-Man: No Way Home, Tobey Maguire’s Peter Parker seemed relatively positive about his time as Spider-Man, which was a change from his time as the web-slinger back in the early 2000s when he was struggling to balance the lives of Peter and the hero.
Between many of his friends and family becoming victims of his enemies and losing his powers in Spider-Man 2, Peter certainly went through a lot of turmoil, showing fans the downside of being a hero. The dialogue in these scenes was also quite memorable too as the screenwriters created some heartbreaking quotes that deeply resonated with fans (which was further enhanced by Maguire's delivery).
Keeping His Feelings From MJ
"I wish I could tell you how I feel about you."
While talking through a payphone in Spider-Man 2, Peter told MJ that he wishes he could tell her how he felt about her. Peter wanted to tell MJ everything but he knew that if she found out who he was and it became widely known that they were together, his enemies could use her against him.
It turned out that this was exactly what happened in each of the Spider-Man movies, with Goblin, Doc Ock, Harry, and Venom using MJ against Peter. Fans now know, after seeing Spider-Man: No Way Home, that Peter and MJ did end up making their relationship work after a while, but it was still hard to see the two suffer for so long because of Peter's responsibilities as Spider-Man.
The End Of Peter And Harry
"I'm done trying to convince you."
One of the main storylines going from Spider-Man to Spider-Man 2 and into Spider-Man 3 was Norman Osbourne's death and how Harry believed it was Spider-Man that killed him instead of his glider. Even after years of trying to convince Harry that he didn't kill his father, Peter eventually finished trying to convince him.
This quote was at a very pivotal moment in the movie as it seemed like the end of Harry and Peter's friendship. With Peter and Harry locked in battle in Harry's home, this quote served as the icing on the cake that the two characters who were once best friends, were now seemingly finished with each other.
The Struggles Of Being Spider-Man
"For Me, The Choice To Lead An Ordinary Life Is No Longer An Option."
This was another quote from Spider-Man 2, one of the best Spider-Man movies, that showed Peter's biggest struggle - how to balance his personal life with being Spider-Man. Sam Raimi's Spider-Man movies had this as a central element of the storytelling. Peter continuously had issues that got in the way of his relationship with MJ, got his Uncle Ben killed, and made him consider if it was worth being Spider-Man.
This was the existential crisis that made him have his "web-block" in Spider-Man 2. It seemed like Peter made it work after all, but as soon as Peter shot his first web, this cleared his chances of having a 'normal' life.
His Role Model
"I Have A Father, His Name Was Ben Parker."
Fans will know that Uncle Ben was essentially the core father figure in Peter’s life after his parents died when he was young. During the final altercation between Peter and Goblin, Norman states that he was like a father to Peter to which Peter replied that Ben was his father.
Goblin was not directly involved in Ben Parker’s death and it does have to be acknowledged that Norman likely did look after Peter due to his friendship with Harry, but no one, aside from his real father, could replace Uncle Ben as the core role model in Peter’s life. They had a special bond that would never be forgotten.
Uncle Ben's Death
"That's my uncle!"
At the beginning of the first Spider-Man movie, comic fans knew that Uncle Ben's death was on the way. As Uncle Ben searched the streets for Peter, he met his demise at the hand of a robber that Peter let go.
Once Peter found out he was lying on the street, fans could hear the pain in his voice as he yelled "That's my Uncle!" Much like in The Amazing Spider-Man, Peter felt like it was his fault that Uncle Ben was out of his house, making Peter have to bear the burden of his Uncle's death (possibly the hardest thing that happened to him).
Still Feeling Guilty
"My Uncle Ben was killed. It was my fault."
The cameos of Tobey Maguire and Andrew Garfield in Spider-Man: No Way Home were handled brilliantly, with the two Spider-Man predecessors serving as older brothers for Holland's incarnation. As the three heroes met for the first time on top of the school roof, Maguire's Spider-Man told Peter of his Uncle's death and that it was his fault.
This wasn't only a desperate attempt to empathize with Holland's Peter to calm him down, but also a reminder that Peter still hung on to his Uncle's death and still felt guilty for it all those years later.
The Downsides of Being A Hero
"Am I not supposed to have what I want?"
After failing to save the last person from a burning building in Spider-Man 2, Peter ended up in turmoil about what his role was and how life isn't really fair to him. While in his apartment, he questioned that he never had exactly what he wanted.
This occurred at a time when Peter didn't have his powers so fans could see a struggling Peter who, when he had his powers, couldn't be with MJ, but even without his powers, he knew he couldn't just walk past and let people die when they were in danger.
Losing MJ
"I know I've been selfish but I can do better, I can change."
In Spider-Man 3, Harry blackmailed MJ to break up with Peter when she met him on the bridge. Even though it pained her to do, she lied and said she met someone else.
Fans saw how these lies broke Peter as he exclaimed that he knew he had been selfish but he was willing to change. This called back to one of the main struggles of being Spider-Man, balancing what Peter wanted against his duties and responsibilities to the people of New York as Spider-Man.
Keeping Those Closest To Him Safe
“No matter what I do, no matter how hard I try, the ones I love will always be the ones who pay.”
As powerful as Peter was, the biggest risk of being Spider-Man was having the people he loves be a target for his enemies. Over the three movies, Aunt May, Uncle Ben, MJ, Harry, and Gwen all suffered in one way or another at the hands of Goblin, Doc Ock, Sandman, and Venom.
Therefore, it's not that surprising that Peter ended up trying to keep his distance or attempted to push people away. Fortunately, despite his personal mission, his closest loved ones refused to listen and persisted in being in his life.
Peter And Harry's Redemption
"I should never have hurt you and said those things."
In the final act of Spider-Man 3, Peter and Mary Jane stand over a dying Harry Osbourne as he succumbed to his injuries after trying to save Peter from Venom. In what turned out to be arguably the most emotional scene in the trilogy, Peter and Harry reflected on their fight and the words that Peter said to Harry about his father being disappointed in him.
As real as it was in the moment, the two realized they were wrong in Harry's final moments. Hindsight was 20/20 for the two heroes as they re-ignited their friendship and became best friends just in time.