It is quite possible for this achievement to come naturally while attempting to get all of Spelunky's achievements. Don't think you're a bad player if you get this without trying because a lot of people will. To speed up the process, if you lose a heart within the first couple seconds of starting a new adventure, or you're finding yourself in a tough situation in the first couple stages, just press , go to End Adventure, then try again. Otherwise, enjoy pressing , ending your adventure, and restarting over and over until you reach 1,000 deaths. You could also just kill yourself in various ways.