30 greatest Deadpool moments in Marvel Comics

A fan cosplays as Deadpool during 2017 New York Comic Con - Day 1 on October 5, 2017 in New York City. (Photo by Roy Rochlin/Getty Images)
A fan cosplays as Deadpool during 2017 New York Comic Con - Day 1 on October 5, 2017 in New York City. (Photo by Roy Rochlin/Getty Images) /
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A Comic Con attendee poses as DeadPool (Photo by Daniel Zuchnik/Getty Images)
A Comic Con attendee poses as DeadPool (Photo by Daniel Zuchnik/Getty Images) /

11. Pirate Deadpool

Norman Osborn’s final attempt at defeating Deadpool was throwing Bullseye at him. The two fought hard and almost killed each other. The problem was, they were having fun. It stopped being fun for Bullseye when Deadpool parked a monster truck on his leg and came after him with a chainsaw.

When Bullseye realized he couldn’t win this fight, he switched tactics from fighting Wade to bribing him. We don’t know how much money he used to bribe Deadpool, but it was enough for Deadpool to do one of the silliest things ever. He became a pirate.

Deadpool bought a ship, a bunch of pirate gear, made his friend Bob dress up like a parrot, and sailed the seven seas. Well, he sailed one sea. Wade was so rich he had a gold gun that shot diamond bullets (he called it The Compensator). Deadpool, Bob, and a blind tour guide Deadpool hired went on to actually do some good. They stopped a group of real pirates that were terrorizing cruise ships.

After one mission Deadpool gave up his pirate life, not before leaving Bob with the attractive tour guide and a treasure chest full of gold coins shaped like Deadpool’s logo. They should’ve never given him money.

As funny as this series was, it led Wade into a journey of self-reflection. He started to hate his immortality. Even worse, he started to realize how alone he really was. None of his friends really like him. He used to act like he didn’t care, but Deadpool started to realize that he wanted to be loved. After some self-reflection and a few hallucinations, Deadpool decided to become an X-Man.

Comics to check out: Deadpool: Wave of Mutilation