What makes Deadpool as a character so appealing? This is the question I’ve failed to properly address as I’ve banged my face into the keyboard for two weeks trying to write about these blasted films. It’s only with this… fourth or fifth draft that I’ve realized the core of my problem: what I personally find appealing about Deadpool versus what others might find appealing. My arguments never felt convincing because I was assuming my readership would feel the same as I do in regards to Wade Wilson.

When it comes to the comics themselves, I checked out pretty early on. I believe I called it quits the very issue that T-Ray revealed himself to be “the real” Wade Wilson while Deadpool was just some sociopath that stole his life. That kind of background swapping complication was precisely why I never got deep into comic books. Moreover, it tries to further complicate the character emotionally in ways that do him a disservice. I have similar issues with Alan Moore’s beloved The Killing Joke. Though it is still left vague and uncertain by the end, Joker is effectively given an origin. An origin that humanizes The Joker, revealing him to be some weak, pathetic little man that went insane off of a bunch of chemicals to the brain. Whereas the Joker was once a threat, he now just seems like a sad, twisted little man with a complex.

This is why I believe Christopher Nolan’s interpretation in The Dark Knight is so popular and beloved. With each person he meets he improvises a new origin for the scars on his face. He enjoys intimidating his victim with the unhinged story of a man that’s been wronged, giving a sense of inevitably lost control. The real threat is that the emotional anecdote is a fabrication. Joker is in control the whole time and is perhaps the most calm person in the room. That he’s so easily capable of manipulating everyone else is where his joy comes from.

Deadpool is not unlike the Joker. By delving too deep into who he was you begin to ruin – and perhaps over-explain – who he is, ruining the magic of his presence in the process. Being a failed part of the Weapon-X program allows us to understand the origin of his powers, but it certainly doesn’t explain his personality. A personality that, quite frankly, needs no explanation. What makes Deadpool so enjoyable as an anti-hero is that he is a personified inside joke. As with any joke, the more you explain it, the more you ruin it.

Anyone can break the fourth wall and point out the absurdity of comic books. The difference is that Deadpool loves being a comic book character, and therefore loves comic books. He’s completely aware that he’s part of a comic, but rather than succumb to the existential crisis of being at the whims of some writers – see Last Action Hero – he plays along. When put beside the self-serious cast of Marvel’s various headline heroes, he pokes fun at their absurdities while simultaneously allowing them to shine brightly. Just see any time he’s had to fight Wolverine or The Hulk.

When he’s at his best, Deadpool reminds comic readers of the absurdity of what they’re reading, but he doesn’t shame them for it. After all, he loves this stuff, too.

That’s my interpretation, at least, and why I first enjoyed reading those early comics. I think it’s also what a lot of people enjoy about the character, but the films have a tendency to falter with the execution. It just happens to be more obvious in the sequel.

Conveying the events of the first Deadpool out of chronological order was actually a pretty clever move. While it perhaps gave a bit too much of an origin for Wade Wilson, it was told in bits and parts so that the audience may have regular, jovial, comically violent Deadpool from start to finish. Interrupted perhaps, but it actually helped the pacing of the film. You were never drowning in the merc’s filthy mouth, but you were never waiting too long to get back to the hijinx, either.

Deadpool 2, on the other hand, plays out sequentially. In order to reach the point where Wade Wilson is assembling a team and starting to have fun with superhero and blockbuster film conventions, you have to suffer through his depressing moping around.

Now that’s a comic that would cause some hairs to stand on end today.

Which, I think, is where I’ve struggled to convey my feelings adequately. Any character, even Deadpool, needs a motivation. The film does everything it needs to give Deadpool a good reason so that the movie can happen. Upon repeat viewings, however, the first act is easily the least enjoyable. On paper the writers did everything correctly. Unfortunately the film just doesn’t feel quite so enjoyable. Not like a Deadpool film ought to.

It’s not the lack of quips or gags. There are plenty of those. Many of them were so memorable that I continued laughing in recollection as I drove home from the theater the first time I saw it. The juxtaposition is in the protagonist himself. The style of comedy these films are going for doesn’t work so well with a protagonist that actively wants to die.

Which is what leads me to the next issue with the film, and perhaps where I’ve had the most trouble conveying my feelings. Vanessa the girlfriend. She allows Deadpool to have greater motivation in the first film than vengeance, but that motivation is effectively “token girlfriend”. She feels like the focus-tested concept of Hollywood producers insisting women won’t be interested without some romance in the flick. She’s the sort of stereotypical character that a Deadpool film should be lampooning, but instead they stuck to the script as rigidly as a predictable double entendre improvised on set by Ryan Reynolds.

My greatest concern with such a character was how she’d be implemented in sequels. Of all the obvious routes they could have gone, they chose the most predictable path of least resistance by shoving her in a fridge. There’s so many reasons this decision is infuriating, but I’ll try to limit myself to just the reasons regarding Deadpool himself.

Killing Vanessa off in the opening act of Deadpool 2 is the writers trying to have their cake and eat it, too. They use her as a convenient plot device in the first film, but once they realize Deadpool as a character just doesn’t work so well with a steady girlfriend they kill her off. This death can then be used to motivate our hero to go on an adventure.

This tripe isn’t Deadpool, it’s the kind of stuff Deadpool mocks and makes fun of.

I will, however, give the writers some additional credit. It would have been easy to simply craft another tale of vengeance. Instead, Deadpool’s motivation throughout the entire film is to do whatever he needs to in order to join Vanessa in the afterlife. In other words, Deadpool’s entire goal is to simply die. Suitably macabre! The problem is no one is really having fun when they try to kill themselves.

I suddenly feel as if I’ve stepped into some dangerous territory here.

For me, Deadpool is at his best when he’s having fun. It takes about thirty-to-forty minutes for him to get over his suicidal moping and finally enjoy himself. To finally be the Deadpool that’s aware he’s in a movie and can play with the audience’s expectations. To take a typical set piece and allow everything to go wrong that can… unless Domino is in play.

The second act of the film is the best because it is the most pure, unadulterated Deadpool experience. It is not bogged down by cheap relationships or over-thought motivations. He’s having an adventure, and we get to have a good time along with him.

Which, finally, might be the greatest reason I’ve struggled with this essay. I really enjoy Deadpool 2! I think Ryan Reynolds and the production teams behind these films really do have a handle on Deadpool’s uncouth appeal.

So why write something so seemingly negative? In part because humor itself is incredibly subjective. I can’t explain what I like about the film without diving deeper into the story’s details and the individual gags and jokes, and to do so would be the same issue I have with giving Deadpool or Joker backgrounds: you over-explain it all.

These issues I have with Wade Wilson’s motivations are really the only thing I think the films have going for them. That, and an overly long death scene that wears out its welcome the first viewing, let alone repeats. I wanted to express them, but each time felt unconvincing. Even this draft, effectively the fifth I have written, feels insufficient.

I think others might be able to grasp what I mean, though. There’s a macabre whimsy to Deadpool that has fun with what he, and we in the audience, love. Once you start taking the character seriously you begin to drown him in sorrows rather than joy. It is in many ways necessary, but to that end I think there simply needs to be slightly more clever writing involved.

Not every scene needs Deadpool, and like the film Dredd, it’s not always the titular character you should be giving an arc. There were plenty of characters in Deadpool 2 that grew. If a Deadpool 3 manages to get greenlit, then those are the types of characters (though not specifically those characters) you focus on giving emotional journeys.

Wade? Well, he’s just along for the ride.