Here is an archive of all the past top five lists I've done over the years.
As Deadpool has become more and more of a popular character, he has made a number of guest appearances over the years. Let's check out his top five guest appearances!
NOTE: It doesn't count as a "guest appearance" if he is in the name of the comic (like Deadpool/Daredevil '98) or if it is a direct crossover with Deadpool (like Part 1 is in Deadpool's comic, Part 2 in the other comic, etc.) or if it is a Deadpool story in an anthology. Also, it doesn't count if he appears as a member of a team in that team's book (like when he appears in Uncanny X-Force, the Red Hulk Thunderbolts or Uncanny Avengers). In fact, I'm also going to go a step further and not count guest appearances where Deadpool appears AS a member of a team (like when the Uncanny Avengers recently guest-starred in Black Knight, for instance). Finally, and this is a tricky one, but I am going to also eliminate all appearances in the pages of New Mutants/X-Force preceding Deadpool's first mini-series. The theory being that until he appeared in his own title, he wasn't really a GUEST in X-Force, was he? He was just an X-Force character period (he even had a trading card in X-Force #1!). Appearances in OTHER books would count, but not X-Force. Once he got his own book, then sure, I'd count them then. Okay, with those rather complicated rules in play, let's see what we can see!
In one of his earliest guest appearances, Deadpool shows up in a back-up story in Avengers #366 by Glenn Herdling, Mike Gustovich and Ariana Lenshoek that continued the story of Bloodwraith, a character that Herdling had just introduced in that year's Avengers Annual. Deadpool and Bloodwraith are both looking for some weapon that is supposedly powerful. The MacGuffin leads to at least an awesome three-way sword duel between Deadpool, Bloodwraith and Black Knight...
Interestingly, the Bloodwraith almost kills Deadpool later in the issue, but the ebony sword had been sated by the sacrifice of Victoria Bentley earlier in the story and so the Bloodwraith doesn't kill Deadpool.
This was part of a crossover with the Punisher and Daredevil that involved a bunch of bad guys meeting in Las Vegas to discuss how to split up the Kingpin's criminal empire (after he was taken down in Daredevil #300). To set the scene, the villain Bushwhacker shows up trying to hunt down a criminal (there representing the villainous Lotus) who Bushwhacker believes has stolen the daughter of Bushwhacker's ex-wife. The guy is there with a prostitute friend of Nomad's. Nomad gives the baby he travels with (who he named Bucky) to the prostitute and then discovers that the criminal is ALSO being hunted down by Deadpool, due to a deal gone wrong between Lotus and Deadpool's then-employer, Tolliver...
Fabian Nicieza wrote this issue, which was the first time Deadpool appeared outside the pages of New Mutants/X-Force, and as the co-creator of Deadpool, he nails Deadpool's appearance here. Pat Olliffe and Mark McKenna drew the issue.
Heroes for Hire #10-11
John Ostrander did a good job capturing Deadpool's voice in this two-parter when Deadpool joined the Heroes for Hire for a mission (regular Heroes for Hire artist Pasqual Ferry penciled the first issue while fill-in artist Scott Kolins penciled the second issue).
Gerry Duggan was writing Deadpool's ongoing series when he took over writing Hulk, as well, from Mark Waid. Duggan began an epic storyline called The Omega Hulk, where the Hulk begins to eliminate other gamma-irradiated heroes. Deadpool plays a key role in the final part of the storyline (the whole thing is drawn by Mark Bagley and Drew Hennessey). First off, he is hired by the Hulk...
And then we learn his role...
Like Nicieza on Nomad, Duggan clearly knows how to write Deadpool, so it works well. And I liked that he played a major role in the storyline.