During Gerry Duggan's post-Secret Wars run on Deadpool, there would be these issues flashing ahead to 2099, showing how things were going for Deadpool. The answer, as it usually is, was "poorly, depending on which Deadpool you're talking about."
You've got one Deadpool in some sort of digital-looking suit, flying around on some A.I. dragon, with a whole legion of "Bobs" for henchmen. She and her crew make "stims", so, drug dealers. Deadpool is supposed to take drugs, not deal them! Worst cosplay ever! But she starts the issue on the run from the police, who she claims she can't actually fight all of. Well, sure, but if you're really Deadpool, you should just enjoy causing as much destruction as you can before being thrown in jail.
Damn, I've become a gatekeeper fan, what a horrifying fate. You know what? Nevermind, you're Deadpooling just fine as you are.
She chooses to escape instead, retreating to a crappy apartment where we find regular Deadpool as an old man with a beard, shackled to an easy chair, forced to watch C-SPAN 2099. Wade isn't happy to see her, and when she asks if that's any way to speak to his daughter, replies he has no daughter. And she replies. . .
This isn't Eleanor though. This is Warda, a child he had with Shiklah at some point along the line. She wants to know where her mother is. Wade's mind is more of a mess than normal, with an additional eighty years of whatever added to it, so good luck. He tells her she's trying to find Jimmy Hoffa, and when she responds she doesn't know who that he is, admits he can't remember either. He suggests Preston might know (where Shiklah is, not who Jimmy Hoffa is), even though they were on the outs as then. Preston was a spy, so she knew all sorts of things. He also says he can't remember why he was angry at her.
Warda tells him she wants to hurt him as much as he hurt her, and sets the C-SPAN on repeat before leaving. Then Wade cries for Eleanor, which um, wrong kid, Wade. But then he notices the Texan up there vowing to dissolve the EPA to solve the problem of the environment, and wonders why everyone doesn't just listen to the Texan?
Elsewhere, the Bobs deliver "stims" to The Rose 2099, who is a woman with either a holographic or actual crystalline rose around her head. On their way home, the Bobs are jumped by a mysterious woman wearing a mask and a red cape with weird white lines on its inner lining. She wants to know how to find Deadpool (meaning Warda), and wants her to know it.
This would run through at least three more of these before being resolved in a larger-than-normal 25th issue. I liked them better than most of the arcs in the present day Duggan did during that stretch. Probably because watching Wade have to deal with a century worth of accumulated family shit was kind of funny.
[3rd longbox, 195th comic. Deadpool (vol. 4) #6, by Gerry Duggan (writer), Scott Koblish (artist), Nick Filardi (colorist), Joe Sabino (letterer)]
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