Deadpool’s Birthday Surprise Moment: Deadpool decides to throw a surprise birthday party for Wolverine, complete with balloons and cake. The catch? He doesn't actually know Wolverine's real birthday. Deadpool’s antics involve him jumping out of a cake and yelling, “Surprise!” only for Wolverine to just roll his eyes and walk away. The absurdity of Deadpool’s over-the-top party planning is classic. Issue: Deadpool #8 (1997)
"The One Where Deadpool and Wolverine Swap Bodies" Moment: Deadpool and Wolverine accidentally swap bodies through a series of chaotic events. Deadpool, in Wolverine’s body, is hilariously ineffective at being the “best there is at what he does,” while Wolverine, in Deadpool’s body, struggles to deal with the constant babbling and erratic behavior. Issue: Deadpool & Wolverine #2 (2009)
Deadpool Attempts to Use Wolverine’s Claws as a Toothpick Moment: Deadpool finds himself in a sticky situation and uses Wolverine’s claws as a toothpick to clean his teeth, much to Wolverine’s dismay. Wolverine’s look of exasperation is priceless. Issue: Deadpool #16 (1998)
Deadpool Tries to "Help" Wolverine with His Rage Issues Moment: Deadpool tries to help Wolverine manage his rage issues by putting him through a series of bizarre and unhelpful “anger management” exercises, such as yoga and meditation. The exercises naturally end in chaos and destruction. Issue: Deadpool #9 (2009)
"Deadpool and Wolverine vs. Santa Claus" Moment: Deadpool and Wolverine find themselves fighting against a Santa Claus who turns out to be a villainous robot. The resulting battle includes ridiculous moments like Deadpool trying to negotiate for better presents. Issue: Wolverine: The Best There Is #6 (2011)
Deadpool’s "Wolverine’s Wardrobe Malfunction" Moment: During a fight, Deadpool comments on how Wolverine’s costume looks like it’s falling apart, jokingly calling it “worn out” and “raggedy.” He even suggests that Wolverine should try shopping at a new store. Issue: Deadpool #50 (2009)
Deadpool’s "Superhero Training Program" Moment: Deadpool creates a “Superhero Training Program” for Wolverine, which includes ridiculous exercises like pretending to be a superhero in public and absurdly exaggerated training regimens. Issue: Deadpool & Wolverine #1 (2009)
"Deadpool’s Awkwardly Bad Assumptions" Moment: In a mission with Wolverine, Deadpool misinterprets Wolverine’s gruff demeanor and makes awkwardly incorrect assumptions about what Wolverine is feeling or thinking. For example, Deadpool might mistake Wolverine’s silence for brooding sadness or philosophical introspection. Issue: X-Force #11 (2009)