Conan

Most easily done on the Squid Boss level. Hit the tentacles of the squid until the squid starts to change the crew into oilmen. Then just grapple as many oilmen until you get this achievement.

i agree with the above solution HOWEVER PLEASE TAKE NOTE that there is no checkpoint between the three boss stages before it pulls itself up onto the boat so MAKE SURE YOU KNOW WHAT UR DOING before spending an hour and a half getting a crapton of grapple/dismemberments only to fail to cut the squid tentacle in time on the third stage and go ALLLLLLLLL the way back to the beginning......not that i did that or nething...

To earn this achievement, you must earn at least two-hundred and fifty grapple kills.

In order to make this easier, you must first reach Act Eight, which is a boss fight between Conan and The Squid. It doesn't matter what difficulty you use for this achievement as long as you arrive at that fight. Once that's done, the real work begins.

In the first phase, you just need to cut down the tentacles that The Squid slams on the ship. When that's done, The Squid will try to capsize the boat by wrapping one of its tentacles around the mast of the ship. Quickly destroy it with a quick swipe or two from your chosen weapon. It will then go away, allowing the next phase to happen, which is phase two.

The Squid will now resort to capturing men on the ship and changing them into oilmen, which happens for a few seconds. When that's done, they will be oilmen for good.

Since you have to rely on grapple kills here, I found it best to use either the backbreaker or piledriver grapple.

For the backbreaker, it's BY. For the piledriver, it's BX. You just need to hit one button, then the next one a short second later for the desired move to be executed. It may take a few tries, but you'll eventually get the hang of it! Once you mastered both moves, just keep on grinding with those kills on the oilmen!

One piece of advice though; make sure you are NOT hitting the Squid tentacles at all. By doing so, you will be forced to move on to the next phase of the fight, thus costing you any chance of this achievement, forcing you to reload your game and trying again at the beginning.

This took me an hour and a half to complete this achievement and then going for the Fatal Touch achievement afterwards. Both can be earned here or if you haven't done it yet, you can earn the first of fifty kills and earn the Man Handle achievement as well, making it three achievements you earned all at once. If that's the case, it may take you a little longer than an hour and a half to earn all three, but it's worth the effort and you'll never have to worry about it again!

Also, to make it easier for yourself, to be on the safe side, make sure you completed the game on King difficulty and turn on the Invulnerability cheat before making it to this boss fight. That way, you won't have to worry about dying by any of the oilmen's attacks or the tentacle assault from The Squid.

Have fun and good luck!

Easily done on the squid boss level (Act 8). After slashing the tentacles that land on the ship and saving it from being capsized the fist time. The squid will transform your crew into oilmen. This is where you grind them out. The squid will keep generating oilmen until you hit the tentacles enough times.

You need to grapple and kill the enemy with a grapple. BX and BY are best, BB usually take a few tries. Should take about half an hour.

The achievement pops in game, so if you do die it isn't a big deal, at least after you have the achievement. Otherwise you'd have to start all over