The Punisher’s entire existence as an antihero has been filled with tragedy and bloodshed. Frank Castle is never afraid to get his hands dirty in order to take down his targets. However, in a promotional comic from 2009, The Punisher faced off against an unexpected foe: rapper Eminem.

Eminem has a surprising history with comic books. When he isn’t performing, the rapper is reported to be a pretty big comic nerd. Not only has he made references to comics in his songs, but Eminem apparently has an otherworldy comic collection with a copy of Amazing Fantasy #15. So, with a passion for comics, Eminem was actually featured in a special promotional comic from Marvel back in 2009.

As Eminem’s album Relapse was coming out, Marvel teamed up with XXL Magazine to publish a promotional comic titled Eminem/The Punisher. The book was written by Fred Van Lente, with art from Salvador Larroca and colors by Frank D’rmata and released in June 2009. The one-shot paired Eminem with one of his favorite comic heroes and remains one of the most insane, bizarre crossovers Marvel Comics has ever done.

In the book, Eminem performs a show and leaves after with bodyguards. The Punisher opens fire on his guards as the rapper hides before meeting up with the villainous Barracuda. Castle tracks them down, but Eminem pistol whips him and shoots him in the chest. Yes, Em takes down The Punisher that easily. Barracuda double-crosses Eminem, shoots him, and brings him and The Punisher on a small boat across icy shores.

On the ship, The Punisher reveals he was trying to protect Eminem, who Barracuda was hired to kill. Eminem wonders how Barracuda could “Judas me like this man? We grew up together.” Barracuda throws Eminem off the ship and says he’ll get the fast track on selling his stuff on eBay, once it goes up in value following his disappearance. Tied up, Eminem doesn’t fall into the water, as thick ice stops him from going under.

The story takes a strange turn. Eminem gets up and walks on the ice (in the middle of the ocean) and finds a man ice fishing. It turns out, the stranger tells him he’s his biggest fan (parodying Stan) while listening to Relapse on his phone. Got to include that album promo. Meanwhile, Barracuda is about to take down The Punisher, when Eminem shows up with a chainsaw and slices through him. The Punisher doesn’t forgive Eminem for trying to kill him and tells him to go out on the ice. Castle shoots the ice surrounding him leaving Eminem stranded. He flips the rapper a satellite phone before leaving him by saying he was going “to pay a visit to the parent’s music council.”

Eminem/Punisher is particularly funny because it clearly tries to make Eminem come across as one of the toughest people ever. In the book, he pulls a gun on The Punisher, managing to shoot the antihero, murders a villain with a chainsaw, and has a tough guy persona throughout the issue. Obviously, they weren’t going to do this crossover without making Eminem look like a badass, but it’s so overdone. Eminem matching wits with The Punisher doesn’t make any sense.

The promotional comic will be remembered as one of the strangest, insane things Marvel ever did - and definitely won’t be remembered as one of the best comic crossovers ever. At least Eminem is a genuine fan of The Punisher, going so far as tweeting his anger when the Netflix adaptation was canceled. Still, the spotlight was highly off and pandered heavily to the rapper’s image. Eminem being on the same level as The Punisher is just incredibly ridiculous - even if it’s just a comic.

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