Joe Kelly's Deadpool (Reading Order)
IF YOU ONLY CARE ABOUT THE READING ORDER, JUST FOLLOW THE BOLD TEXT.
The first long-term run that Deadpool had began in 1997 and was written by Joe Kelly. This is generally considered one of the better runs on the character, and introduced or developed many of the character traits and supporting cast we associate with Deadpool today (e.g. 4th Wall breaks, Blind Al & Weasel, etc). With that said, here's the order:
Deadpool (1994 Limited Series) #1-4
Deadpool (1997 Series) #1-5
Deadpool (1997 Series) #-1
The '94 Limited Series wasn't written by Joe Kelly (it's actually written by Mark Waid and features some of my favourite Deadpool writing), but Kelly's run begins right off the back of it. It's Deadpool's second ever limited series, and unlike the first one, doesn't really tie much into any other plotlines. It's just a Deadpool book. This also sets up Deadpool's first meeting with Siryn, and a couple other moments and plot elements that come up during Kelly's run.
#1-5 is the first story arc of Kelly's run, and more or less deals directly with the events of the previous series. As for #-1, this was part of a series of issues in a pseudo-event called "Flashback". While the issue, I believe came out after issue #6, narratively it fits a bit better here, since 6 is the beginning of the second arc. While there may be narratively an even better place for this issue, placing it here at least means you'll have read it any time the issue is referenced going forward.
Deadpool (1997 Series) #6-7
Daredevil/Deadpool Annual 1997
Deadpool (1997 Series) #8
Deadpool (1997 Series) #9
Deadpool (1997 Series) #10-11
Deadpool (1997 Series) #0
Issues 6-8 + the 1997 annual make up one story arc, while 9-11 make up another. Issue #0 is basically entirely disconnected from everything and is only worth reading if you're a completionist. It IS at least written by Joe Kelly, which is why it's here at all.
X-Force issue is essentially a cameo. It's referenced in Deadpool #10 but not required reading by any stretch of the imagination.
Side note, I also struggled to figure out quite when it was released. The Marvel Unlimited app says December '96, but the wiki says Jan '98. The issue also makes reference to the events of Deadpool #6 and says that they happened a year ago, so I'm inclined to believe the wiki.
Deadpool (1997 Series) #12-14
Deadpool (1997 Series) #15-17
Deadpool & Death Annual 1998
Deadpool (1997 Series) #18-19
Deadpool (1997 Series) #20
Deadpool (1997 Series) #21-22
Here are some more arcs. Deadpool makes significant guest appearances in Heroes for Hire, and I believe issue 10 indicates that the story takes place sometime after DP17, but since that's the middle of a story arc that has no space to be interrupted, I looked for the next most appropriate place for it. The story ends kind of abruptly though, particularly for Deadpool's involvement.
Deadpool (1997 Series) #23-25
Deadpool (1997 Series) #26-27
Deadpool (1997 Series) #28-30
Deadpool (1997 Series) #31-33
Here's the last stretch of the run! once again broken up into story arcs (although given their lengths, it may be more appropriate to call them segments of story, especially since everything after Issue 25 feels almost like an epilogue).
Wolverine Annual isn't written by Joe Kelly, or refer much to the actual plot of the run, but Deadpool makes a significant guest appearance in it, and there is explicit reference made to the events of Deadpool #27
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