Deadpool and Spider-Man are a fan-favorite comic pairing, a perfect match of smart-aleck wise guys who fight crime. As soon as they were allowed to team up together, fans jumped all over it, producing memes and videos and jokes all their own. The two costumed characters also have a rich history within the comics themselves, helped by their recent and ongoing team-up series. Their relationship may have started out antagonistic, but it eventually turned into one of respect, affection, and friendship. Granted, they've had some rough spots here and there, but nowadays they're very good chums.

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With a character as wacky as Deadpool - the Merc with a Mouth who knows he's in a comic book and breaks the fourth wall - teaming up with Spider-Man - the Wall-Crawler with much more integrity and morals who is just as quick with the witty retorts - it should come as no surprise. From their own personal dynamic to the villains they've fought to the times they've fought each other, it's one strange moment after another with Spider-Man and Deadpool.

Updated on December 21st, 2021 by George Chrysostomou: Deadpool and Spider-Man could be very well be crossing over in the Marvel Cinematic Universe very soon and the comics could hugely influence how their relationship plays out on screen. These facts are surely vital in understanding how Marvel Studios will approach the friendship, with Ryan Reynolds and Tom Holland in the two titular roles. 

They Weren't Very Friendly When They First Met

Spider-Man fights Deadpool in Marvel Comics

While various versions of Spider-Man and Deadpool had met in other issues - usually in storylines where Deadpool went into the past, or an alternate universe, or met an alternate version of Peter Parker - the two characters didn't cross paths in the prime Marvel continuity until 2006, with Cable/Deadpool #24. In that issue, Deadpool wasn't even trying to meet Spider-Man, but instead was trying to find another Daily Bugle reporter. That reporter was driving with Peter Parker over a bridge when Deadpool finally caught up with them, and the scene didn't play out in the friendliest of ways.

Deadpool throws Peter Parker off the bridge. That's the first interaction the two heroes ever had. A fight breaks out, as Spider-Man appears (who would have guessed?) and takes issue with the Merc with a Mouth. Spidey keeps trying to fight Deadpool and protect the reporter, while Deadpool seems to be more focused on making jokes about Tobey Maguire. This issue set the tone for a lot of Spider-Man's early run-ins with Deadpool, as instead of being smart-alecky like normal, the Wall-Crawler acted as a straight man for Deadpool's wacky attitude. It wouldn't be until later that the two found a rhythm where they could both be funny in the same conversation.

Spider-Man and Deadpool in Marvel Comics

It doesn't take much brainpower to realize that Deadpool's look was based on Spider-Man's when comparing the two side by side. The color scheme, the skintight design, and especially the cowl are all very similar. Heck, one look at Deadpool's eyes should make it clear that Spidey's eyes inspired them. Deadpool's creator, Rob Liefeld, has itted as much, saying that he didn't have access to Wolverine or Spider-Man, so he had to make his own. Liefeld's other famous creation Cable resembles Wolverine in spirit, and Deadpool's look is undeniably based on Spider-Man and the DC assassin Deathstroke.

The look is so similar that pretty much every story that has both characters brings it up. When Deadpool makes an appearance in the Deadpool film actually took it further. In an early draft, Deadpool supposedly couldn't figure out his costume, so he found Spider-Man's cowl lying around on the street, turned it inside out, and that was his costume for the movie.

They Watched Batman V. Superman Together

Batman vs Superman Marvel Comics parody with Deadpool and Spider-Man

Deadpool has always been one to break the fourth wall, and since he resides in the world of superheroes and villains that means that he tends to comment on the tropes and trends of that genre. So in the comics, the Merc with a Mouth goes to see superhero movies in his spare time - and who better to bring along on a movie date than his friendly neighborhood Spider-Man? One of the early sources of conflict in Spider-Man and Deadpool's ongoing team-up series was that Spider-Man didn't want to hang out with Deadpool when they weren't fighting crime. They tried to solve that by seeing movies.

Obviously, the two characters seeing a superhero movie gave the Marvel writers a chance to rag on the DCEU, and they weren't going to waste a chance like that. Specifically targeting Batman v Superman: Dawn of Justice with a poster that reads "Nighthawk v. Hyperion: Yawn of Boredom," the writers didn't stop there. Spider-Man and Deadpool continue to levy thinly-veiled criticisms of the DC film for several s. While some DC fans may take umbrage at this gag, many more open-minded fans likely thought it was a cute way for Spider-Man and Deadpool to deepen their friendship.

They Trade Yo Mama Jokes

Spider-Man and Deadpool faces teenagers in Marvel Comics

Honestly, it would be more surprising if this wasn't a key component of Deadpool and Spider-Man's relationship. The two costumed characters are each known for their smart-alecky ways, so naturally, their banter would be even better together. In Amazing Spider-Man #611, Deadpool picks a fight with Spider-Man both physically and verbally. He starts by asking for Spidey's autograph with a pen that turns out to be an explosive, and the situation soon devolves into name-calling and yo mama jokes, on both sides. It's slightly jarring to see Spider-Man roll with jokes about his deceased mother.

This absurd scenario wouldn't be complete without an audience of excitable teenagers playing basketball, of course. The whole thing builds up to Deadpool teasing some kind of perfect, atomic yo mama joke (censored, naturally, for the readers' innocent eyes). Eventually, Deadpool leaves, since his contract was only to distract the Wall-Crawler, not end his life. The whole encounter, first revealed in late 2009, feels now like a preview for their eventual team-up series, which is still going on today. The insult exchange is indicative of the two characters' whole dynamic, at once antagonistic and friendly, insulting and profane at the same time. More importantly: it's funny!

Deadpool Has Pretended To Be Both Peter Parker And Spider-Man

Spider-Man loves Deadpool in Marvel Comics

Deadpool and Spider-Man may have very similar costumes, but that doesn't mean they haven't done a swap every once in a while. What's odd is that Deadpool's pretended to be both the Wall-Crawler and his mild-mannered alter ego Peter Parker-- without knowing the connection between them. The first time the two characters ever shared a (outside of the main continuity) found Deadpool traveling to the past and ending up in one of Spider-Man's classic issues. He faked a phone call to Peter Parker to get him out of the way, then pretended to be Parker to aid his own agenda.

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Deadpool also pretended to Spider-Man much later in the comics, but this time, it was for a more altruistic reason. Spider-Man was under attack from a villain called the Chameleon. A master of disguise, the villain kept popping out and stabbing Spidey, which turned the normally calm hero into a nervous wreck. Deadpool, ever an ally, dons Spidey's costume to beat the Chameleon at his own game. The story by Christopher Hastings is a fun one, as Deadpool proceeds to get really excited about running wild in Spider-Man's rogues gallery. The best part? Deadpool saves the day, looks good doing it, and even gives Spidey's public image a boost, much to Peter Parker's bewilderment.

Deadpool Has Tried To "Un-Alive" Spider-Man Many Times

Spider-Man and Deadpool in Marvel Comics

Deadpool makes his living as a mercenary and assassin, so it shouldn't be a surprise that he has a fairly long list of people he has eliminated. For a long time, his basic storylines mostly involved him meeting up with some superhero/villain and doing something to annoy them, causing a fight to break out. Thus, Deadpool fights almost everybody he meets at some point or another, and Spider-Man is no exception. Deadpool has earnestly attempted to take out Spider-Man and Peter Parker on more than a few occasions.

While Deadpool usually doesn't succeed in that goal (or changes his mind because his conscience gets the better of him), there are a few disturbing incidents where he actually did. There are a couple of memorably titled Deadpool series that see the Merc with a Mouth terminate every single Marvel character, and that includes Spidey. The first time is less interesting, as Deadpool's motivations are just that he realizes he's in a comic book, so none of it matters. He shoots Spider-Man at close range there. The second is weirder: Deadpool is deceived into thinking he's actually having wacky hijinks with the other characters, nothing lethal involved. While Deadpool thinks he's having an eating contest with Spider-Man, the Wall-Crawler is actually the one getting eaten by none other than Venom.

Deadpool Appeared In Spidey's TV Show

Deadpool vs Spider-Man in Ultimate Spider-Man

Deadpool appeared as an antagonist in Ultimate Spider-Man, and he showed up to teach Spidey some tricks of the trade. Of course, he's eventually revealed to be actively betraying S.H.I.E.L.D., so he and the Wall-Crawler have to fight over important data.

The episode ended up showcasing why fans love the two characters and their relationship so much, throwing Spider-Man into Deadpool's zany world and allowing both of them to get plenty of jokes in. It all culminates in a "fantasy fight" where they each try to mentally manipulate each other in increasingly silly scenarios. Perhaps the biggest surprise of the whole episode? Deadpool is funny and fun even though he's on a kid-friendly TV show. Even without cuss words or gore, he's able to bring the laughs and the same manic energy he's famous for.

They Had A Very Different Relationship In The Ultimate Universe

Ultimate Deadpool in Marvel Comics

The Deadpool that appeared in the Marvel Ultimates universe was considerably different from the Wade Wilson fans know and love in the main continuity. Instead of the cancerous flesh found on normal Deadpool, Ultimate Deadpool (who went by "Wadey" Wilson) had barely any flesh on his face at all, and it was encased by a glass mask. Instead of a sometimes-friends, sometimes-rivals dynamic, Ultimate Deadpool and Spider-Man had a much more straightforward relationship: Villain and hero. Ultimate Deadpool wasn't an antihero or even morally gray like his mainstream counterpart: he was just evil.

Wadey Wilson didn't even have the same sense of humor that normal Deadpool had. He wasn't without jokes, but they tended to be of the sadistic, evil kind. The character's design was clearly based on Sin-Eater, another Marvel villain, rather than the original Deadpool. The Peter Parker from the Ultimate universe was mostly the same as his Earth-616 counterpart, and since he's a quintessential hero type, there's no way he'd get along with Wadey. Funnily enough, while Ultimate Deadpool's claim to fame came through his run-in with Spider-Man, it was actually Earth-616's Deadpool (i.e. the mainstream continuity Deadpool) who finally put Wadey down for good.

“What If Venom Possessed Deadpool?”

Deadpool - Venom variant cover

That's not just a question from a speculative fan. Marvel has done several issues of comics in their "What If?" universe that allow writers to explore strange alternate universes in the comics. One of these alternate universes had a fairly straightforward idea: what if the alien symbiote had attached itself to Wade Wilson? Unfortunately for Peter Parker, that set-up involves him and the Beyonder. The Beyonder, a nearly all-powerful being, ends up manifesting as a pretty normal-looking dude who goes around in a flying limousine.

Deadpool initially finds the Beyonder in the flying limo to satisfy a contract, which he promptly reneges on because he ends up liking the Beyonder. The two hang out but are found by Spider-Man with the alien symbiote suit. Spider-Man blames the Beyonder for his current suit situation, but that doesn't help him much in the ensuing fight, as he gets blasted out of the sky and the symbiote jumps off him and onto Deadpool, where Venom winds up taking just as wild a ride as Deadpool. What follows is an adventure worthy of the Merc with a Mouth, and an outright strange one, given that it starts with Deadpool, Spider-Man, and the Beyonder in a flying limo.

Spider-Man Is Deadpool's "Heartmate"

Deadpool about to kiss Spider-Man in Marvel Comics

Poor Deadpool. The man is a raging ball of libido, yet his off-putting, decaying appearance makes him a less-than-desirable partner for most. Then there's the whole thing that he's a hardened assassin who hears multiple voices in his head. It's hard for the Merc with a Mouth to get a date, but that doesn't mean he won't try. One of the targets of Deadpool's affections is none other than Spider-Man, though unfortunately for Wade, the attraction isn't reciprocated. While Deadpool has said that he isn't attracted to Spider-Man, some recent events made it clear that he wasn't being entirely truthful. First, there was a magic spell performed on Deadpool meant to summon his wife (yes, Deadpool had a wife, she's a succubus called Queen Shiklah, don't worry about it).

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The spell summoned Deadpool's "heartmate," who turned out to be none other than Spider-Man, rather than his wife. On top of that, in Spider-Man/Deadpool #4, it's revealed Deadpool has a top-five free list that allows him some very specific infidelities. Number five on that list is Spider-Man, which is confirmation that Deadpool wouldn't mind if their relationship was a little more physical and a little less platonic. Spider-Man, on the other hand, has never indicated any romantic interest in the Merc with a Mouth, so fans may have to wait a while for that ship to come in.