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″I got some new friends now. A bunch of ‘em. Figuring out how that should all work. Might take me a while.” Cable & Deadpool (2004) #1 vs. #50
This character arc and the parallels between the first and the last page cured everything that ails me.
Agent X #4 by Gail Simone and Udon Studios
A few underrated raw moments from the Deadpool comics. (Underrated = None of the recent hell from “Despicable Deadpool” or the Secret Empire arc, nothing related to the fantastic "The Good, the Bad, and the Ugly" arc, not the infamous Typhoid Mary scene, not Cable's main touching goodbye, not the "we keep doing stupid things to stay together" Cable scene, nothing with Ellie or Evan, not his death during the Incursion, etc.)
When Wade was sadistically mocking Wolverine with a plan to 'kill' him, transparently overcompensating and insisting that he didn't need Logan's approval or anyone else's (he does), having flashbacks to his abusive father and hallucinating the whole time, only to be thrown completely off-guard and uncharacteristically speechless for a few moments by Logan saying, simply, "You're not crazy." [Wolverine: Origins #24]
The time they tried to get the soul of one of his closest friends, Emily Preston, out of his head and into a new mechanical body, and they thought they were being sabotaged because things went wrong, but it was actually Wade's fear of being alone again causing his own subconscious to attack her. When he woke up, he ran away before she did because he felt guilty and embarrassed. [Deadpool (2012) #24]
When Wade and Cable tried to figure out who'd murdered a terrorist Cable was trying to make peace with, only for them to realize Wade himself had done it and couldn't even remember because of his brain damage and memory problems. He spent an issue fantasizing about all of the heroic reasons he could have had to kill the man, only to acknowledge to himself with shame that he'd probably just felt like it. Cable threw him out of his utopia and when Wade asked what he'd do if he messed up like that again, Cable told him he'd kill him. Wade called it the one question he actually didn't want to know the answer to, and upon getting that answer from his best friend, the one person that really accepted him at the time, he decided to kill himself. [Cable & Deadpool #14]
That time Cable died and Wade took his metal arm- the only part of him that remained- on an absurd trip to the country Cable had saved, forcing people there to respect him and ultimately saving the day with a humorous combination of his and Cable's powers while reminiscing about their relationship, only for it to be revealed that he'd been standing by Cable's grave the whole time, just mourning and trying to figure out how to process the loss. Within that issue: "He had the whole world on his mind, not just the two of us. [Memory of Cable: “I can’t be mad at you for being who you are.”] See? Nate understood me like nobody else." [Deadpool & Cable #26]
When he'd been led to believe he could fulfill a world-saving prophecy by defending an alien "Messiah" from another alien that would try to assassinate it. He struggled for a long time to be a better person that was worthy of the task and fought harder than he'd ever fought before only to humiliatingly lose the big fight against the assassin alien. In one of the most vulnerable, raw moments I've seen from an adult male character, he ran away from the botched fight and went straight to Blind Al, sobbing in her lap because he “wasn’t good enough.” [Deadpool (1997) #23]
That panic attack he had in front of Cable after his face was exposed in a fight with him. He tried to run from the fight but Cable was angry and wouldn't give him a break. [Deadpool (1997) #22]
When Deadpool became “Zenpool” during the Axis arc and it looked like it’d be all fun and games, but he struggled with usual tasks, felt like he was disappointing his family, and ultimately concluded that he was legitimately depressed after things went back to normal. “I ruin it because I can... because it’s easy.” [Deadpool (2012) #37]
When Deadpool didn’t want Cable to leave him again, and any of the times he notes missing him. [Deadpool & Cable #25]
Deadpool’s friend/assistant, Sandi, was hospitalized by her abusive boyfriend and he felt incapable of comforting her, believed that she wouldn’t want someone like him hugging her and telling her things would be okay, and noted that he’d lost the ability to cry or scream about things to feel better. [Deadpool (1997) #69]
EDIT: When Steve Fucking Rogers, his hero (or at least, the Hydra version, but Wade didn’t know that), punched Wade and called him “just another failed experiment” because he’d disobeyed him to help the mutants. To help Rogue, his best friend, and his daughter. (I said no Secret Empire because it’s low hanging tragedy-porn fruit but Uncanny Avengers is underrated enough to count anyway.) [Uncanny Avengers #14]
Deadpool (1997) #65
Sandi and Inez are me. I am them.
Cable & Deadpool #39
DEADPOOL AND HIS PALS
Character: Sandi Brandenberg
Actress: Judy Greer
Storytime with Tasky and Friends! by Camila Ambia Wang