Dying 100 times is way too much to ask in this game. You'll likely die a few times along the way but this is going to be a grind. The best thing to do is start a new game and complete the first two missions until the other missions appear on your minimap, then go straight to work on the Yuri Khovansky missions (marked by an X). His last one, Release, is special because when you fail, you don't have to drive back to a mission marker to try again. Just throw on a movie and keep letting Khovansky kill you, hit restart, skip cutscene, get killed, repeat. This can take an hour or so, depending how many deaths you still need after you beat the game.
There is no way to replay missions so just pick if you've already beat the game, just play up to Release and grind it for this achievement, unless you want to play more of this masterpiece.