Can easily be done with 2 controllers. I chose Act 1-Curtain 2-Screen 1, right after your cutscene with the Witch and Calibrus. Simply move Player 1 down to the far left of the screen and use Player 2 to remove your head (
3x), drop it on the angled vine and it should roll right back to your main character. Wash, rinse and repeat 99 more times and the trophy will pop.