Grand Theft Auto III - The Definitive Edition

Best done early on in the game. Save your game beforehand in case you go too far, then start a fight with someone and let them beat you up until you're either below or nearly at 10hp. Once there make sure you kill them then go somewhere safe and just stand there for 1 minute until the achievement unlocks. You can even jump down the stairs near your safehouse in Portland to do minor damage to yourself (1 or 2hp a time) to get yourself just below 10hp.