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Before his 70 issues long solo ongoing, Deadpool has:

Deadpool (vol.1.) #1-4
Deadpool (vol.2.) #1-4
Baby's First Deadpool Book

That is too little for one bound volume, so the first volume *must* incorporate at least a bit of his ongoing series.

Looking forward a little, towards the end of the second volume, good breakpoints are after #25 (the conclusion of the Landau, Luckman & Lake storyline) and after #33 (the departure of writer Joe Kelly from the book). By the time of #33, we will also have these extras to consider:

Daredevil/Deadpool '97 Annual
Encyclopaedia Deadpoolica
Deadpool/Death '98 Annual
Deadpool Team-Up #1

So by the end of #33, we have #1-33, plus 13 other issues to cover. That's a total of 46. Could be done in two thick 23 issue volumes. Or three thin 15 issue volumes.

Another option is ending a volume at #25, which would mean #1-25 plus 13 issues: 38 issues, which would be quite nice for two 19 issue volumes. But honestly I think it's good to have Kelly's entire run together, so I wouldn't end a volume at #25, only to leave 8 issues of Kelly dangling to the next volume.

So, a rough breakdown:

Volume 1:

Deadpool (vol.1.) #1-4
Deadpool (vol.2.) #1-4
Deadpool (vol.3.) #1-11

Volume 2:

Deadpool #12-33

Volume 3:

Deadpool #34-50

Volume 4:

Deadpool #51-69

There's also 14 volumes of Agent X, which could perhaps be bound together with the 4-issue Taskmaster LS.