I really want to get into Taskmaster more but I'm not sure where to start. Some writers just don't write him well at all. I currently have his mini from 2002. Any other recommendations?
Best Taskmaster books?
There's a lot of good overlap between Deadpool and Taskmaster as well, especially some of Deadpool's older stuff. I think the Simone run had some of that as well, but I might just be thinking that because she liked to pair him up in non-heroic living situations with other villains (e.g., Constrictor, Titania, Rhino).
I'm specifically remembering a more recent scene, however, where Taskmaster is kidnapped by Wade and forced to fight him to prove how tough he is and get more mercenary contracts. Wade and Taskmaster have it out and nothing Taskmaster does to him sticks. In the end he thanks Taskmaster for throwing the fight in front of all the military big-wigs. Taskmaster explains—angrily at first but then more sympathetically—that he was not throwing anything, and that Wade really is that unkillable, but without professionalism nobody wants to hire him. It was a kind of a bittersweet moment for Taskmaster fans since he got his butt handed to him (Traditionally, Taskmaster is always defeated by Deadpool because his powers are of limited use against Wade, whose moves are too "unpredictable" or some such jobber garbage. This was a pure beatdown while Deadpool was handcuffed.), but it was also a heartwarming moment between two friends (Taskmaster describes him as "a friend I can't stand") that have a lot of history and have seen a lot of great development in the last decade.
Cannot for the life of me remember where that scene was from. To the google!
Oh, apparently someone posted scans of most of the fight here on a CV battle thread. Not seeing a source though. Or the dialogue immediately after the fight. Hmm. Reverse-image search, thou hast failed me for the last time.
@fodigg: I'll help you out dude, Cable & Deadpool #36 - Unfinished Business: Part 1 is the issue you are referring to.
@darthaznable: If you really enjoyed his Udon run from 2002, then I'd also recommend Deadpool #68 - Healing Factor - chapter 3: Headbanger's Ball, Deadpool #69 - Healing Factor - chapter 4: Finale, and the Agent X run (from Agent X #1 - Dead Man's Switch, Part 1 up to Agent X #15 - Deadpool Walkin', Part 3: A Means to an End), that followed and finished that particular story-line.
Aside from those, his time in Avengers Initiative is some good stuff, particularly the Siege of Asgard Avengers: The Initiative #32 - Seize The Day to Avengers: The Initiative #35 - The Hammer Falls, Conclusion.
I won't bother listing all of his Deadpool crossovers, but if you can track them down the majority are some entertaining stuff.
I'm not sure if you would consider his original appearance well-written or not, considering that on one hand it is his original, definitive self whilst also being very two-dimensional as a character. Either way, the story-line begins here: The Avengers #194 - Interlude, he first appears here: The Avengers #195 - Assault on a Mind Cage and first battles the Avengers here: The Avengers #196 - The Terrible Toll of the Taskmaster.
You may be interested in Secret Avengers Volume 2 as well, especially since it features his most recent appearances.
As honorable mentions, some of my personal favourites have also included: Daredevil #292 - In Battle With the Punisher-Daredevil #293 - A Bullet for the Punisher, his appearances throughout Deadpool Kills the Marvel Universe, his part in Secret Avengers Volume 1 (from Secret Avengers #29 - A Council of Masters to Secret Avengers #32 - To Hold a Black Hole), his chapter in Marvel Comics Presents #2 - Vanguard Chapter 2: No Earthly Means / Hellcat: The Girl Who Could Be You part 2 / Taskmaster: Best Offense / Weapon Omega Part 2 and the Siren miniseries from Siren: Infinity #∞ - Infinite Possibilites to Siren #3 - Choosing Sides (Siren Special #1 - Know Thyself although being the final conclusion of the story-line does not actually feature Taskmaster).
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