He was created as a 1990s cliche with big guns, big muscles, and an overly-violent attitude, was remade into the fourth-wall-breaking Merc with a Mouth that readers better know today and ended up as Marvel's main channel in which to satirize itself and comics in general. These are every Deadpool run, phase, and series.
The essential reading order goes as follows:
Skip the early stuff and jump to
Joe Kelly's Run
Christopher Priest's Run
Gail Simone's Run
Agent X
Cable and Deadpool, if you must
Daniel Way's Run
David Lapham's MAX Run
Gerry Duggan & Brian Posehn's Run
Cullen Bunn's limited series
Spider-Man/Deadpool
Unbelievable Gwenpool
Skottie Young's Run
Kelly Thompson's Run
Top Ten ranks as follows:
10 - Gail Simone's Run
9 - Deadpool vs Carnage
8 - Night of the Living Deadpool
7 - Spider-man/Deadpool
6 - Hawkeye vs Deadpool
5 - Suicide Kings
4 - Deadpool Kills the Marvel Universe
3 - Deadpool MAX
2 - Gerry Duggan & Brian Posehn's Run
1 - Joe Kelly's Run
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