[hijack]
My favorite Samurai Jack episode. I love the beggining of it. I was watching an episdoe the other night that began the same way, only the other character was a big black strong pimp looking guy. Awesome episdoe, but I missed the ending. You wouldn’t happen to know how it ended would you?[hijack/]
After Jack beats the guy seven ways to Sunday, a bunch of evil robots show up to kill Jack. One of them shoots the wannabe Samurai with a neck-cuff ray (green beam of energy hits him, turns into a giant metal cuff around his neck.) Jack pounds the robots into scrap, then breaks the cuff on the guy’s neck. He’s all ashamed for being such a punk, then notices that the robot remains have rebuilt themselves into a new, giant robot, and pushes Jack out of the way of an energy beam. Jack kills the giant robot, and tells the wannabe guy that, having learned humility, he has learned the first step on the path to being a true samurai. As Jack walks into the sunset, the wannabe guy chases after him, asking what the second step is.
Right, so far, IMO, Hammer, HPL and don’t ask have posted items that best fit the OP’s premise.
I’ll suggest a few. Marlon Brando seems to have a masochistic tendency to get himself beaten to a pulp in some of his films, particularly his Terry Malloy (roundly thumped by Lee J. Cobb) in On the Waterfront and as Sheriff Calder (by an entire town, IIRC) in The Chase. His Stanley Kowalski also gets himself roughed up pretty good in Streetcar Named Desire though it seems to take place mainly off screen.
For sheer psychological as well as physical torture, it’s hard to top what Robert de Niro and John Savage go through during the first ‘Russian Roulette’ scene (while captives of the Viet Cong) in The Deer Hunter.
Bruce Willis has his moments, most notably the various gauntlets he has to run, in his blood-soaked wife-beater T-shirt, in the first two Die Hard films.
Then there’s our man Clint (Eastwood) whose bare-knuckles brawler gets pounded nine ways from Sunday about every five minutes in the two Every Which Way* movies.
And of course, although maybe it doesn’t count because the character isn’t exactly human, the apocalyptic hammering taken by Arnold Schwarzenegger in all three Terminator films probably deserves mention.
Lastly, and possibly the hands-down winner, Jesus of Nazareth in a recent film directed by the aformentioned Mr. Gibson.
How about the scene in “Unforgiven” where the sheriff (Gene Hackman) gives English Bob (Richard Harris) a public ass kicking.
I was gonna mention that! And it even fits the “masochistic” part of the OP title because English Bob knows just how dangerous Little BIll is; and he takes his beating like a dog because he knows that if he offers one shred of resistance, Bill will beat him to death.
I liked the “Hulk Smash” move where she hits the floor with her fists so hard that the shockwave knocks opponents off their feet and the cracks in the ground swallow them up! 
Cletus Snow getting is ass kicked by the bikers in Smokey and the Bandit.
Otter getting ambushed by Greggy and Dougie and the rest of the Hitler youth in Animal House.
Leonard Smalls playing with H.I. like he was a rag-doll in Raising Arizona.
The beautiful part to all of these is that it’s the protagonist getting the severe beat down … followed by sweet revenge.
How about Ash in the first two **Evil Dead ** Films? He got pretty beaten up in both…and the 2nd one had that nice fight againest his hand.
I’m so glad I wasn’t the only person to do that.
Taking the title literally, I’m not sure there’s a better answer than Ichi vs. Kakihara in Ichi the Killer.
How is Tyler Durden, the alter-ego of the Narrator of Fight Club, beating the Narrator to a bloody pulp and then having the fight end in a gunshot to the jaw not masochistic?
Because they’re two different characters, even if they’re technically the same person. Although Jack is only beating himself up, he’s doing so in an attempt to destroy another “person” who just happens to be a splintered part of his own psyche, not in an attempt to destroy himself.
Or, possibly, because I overlooked the earlier mention of Fight Club
Although Jack in his boss’s office was even better, masochistically-wise.
In the original Cape Fear, Gregory Peck’s character, against his better judgment, gets talked into sending a bunch of hoods after Robert Mitchum, a psychopath ex-con who has been terrorising Peck’s family.
The hoods catch Mitchum on a beach at twilight and chase him under a pier; in the audience, you’re rooting for the hoods, but…Mitchum is a tough guy, and he gets the better of them and beats them up (I think he grabs a chain from one of them at one point?) and at the end of the scene, he knows who’s done it and you know that he’s going to go after Peck’s family without remorse or pity. Shiver-down-the-spine stuff, IMHO.
To clarify - I mean masochistic in the sense of scenes that are painful to watch, but still put a grin on your face. Hence, masochism on the part of the viewer.
You youngsters need to rent more older videos, (does not apply to jinty) in 1942’s The Glass Key William Bendix, as a mob-muscleman beats the crap out of the hero, Alan Ladd, all the while calling him “baby” in a little boy voice. This scene is so eerie I cringe just thinking about it.
Read about it here.
Kurasawa openly admitted to being inspired enough by this scene to have Toshiro Mifune beaten the same way by a huge brute in Yojimbo.