Punisher have had some bloody brawls throughout the years, but one fight took things to a whole other level. Frank Castle has his armory and Logan has his claws and a healing factor, so the two find themselves more or less evenly matched in any fight. Their brutal encounter in the early 2000s pushed things even further, as Castle pushed Wolverine's healing factor to the brink.

Wolverine and the Punisher’s most brutal encounter came in The Punisher #16-17 by Garth Ennis and Darick Robertson. Ennis had just recently rebooted the Punisher as a part of the Marvel Knights imprint, which brought Frank Castle back to his gritty, street-level roots.

The two heroes run into each other while on the trial of mobster Tony Casino, who has been kidnapping gangsters all over New York and chopping their legs off at the shins. The Punisher wastes no time upon running into Wolverine, giving him a face-full of twelve-gauge buckshot as a greeting.

The Punisher and Wolverine Have Their Most Violent Fight - Ever

The Punisher #16 by Garth Ennis, Darick Robertson, Matt Milla, Wes Abbott, and Richard Starkings

Wolverine survives the blast thanks to his healing factor, although he spends the rest of their “team-up” missing his face, leaving just his Adamantium skull on display. While they don’t necessarily work together, both Wolverine and the Punisher wind up taking on Tony Casino’s forces. They ultimately prevail over Casino, although the Punisher turns on Logan at the end, knowing the X-Man will attempt to bring the gun-toting vigilante to justice. The Punisher slows Logan down by shooting him in the crotch before crushing him underfoot by literally flattening Wolverine with a steam-roller.

The whole encounter is pure Looney Tunes – little more than an ultra-violent showdown between the Road Runner and Wile E. Coyote, as the Punisher and Wolverine keep trying to one-up each other in increasingly brutal ways. Wolverine’s healing factor means that he can take all the punishment that Castle can deal out, and Frank doesn’t hold back anything when taking the X-Man on. Given that this is Frank’s title and writer Ennis doesn’t care for superheroes like Wolverine, the Punisher winds up coming out on top of this particular fight, but the truth is that a battle between the two could go either way.

The Punisher Pushes Wolverine’s Healing Factor to the Limit

An Unforgettable Wolverine Moment

Fans would think that Wolverine and the Punisher would get along better thanks to both heroes’ willingness to exercise lethal force. But like many other heroes in the Marvel Universe, Logan sees Frank Castle as being just as bad as the villains he puts down. The two have teamed up on more than one occasion, however, and it hasn’t always led to them fighting tooth-and-nail. The Punisher may have gotten the upper hand over Wolverine in this one particular instance, but there’s always the next round to even the odds.

The Punisher #16 is available now from Marvel Comics.