22. 'Poison Ivy' (1992)
Leo's literally only in this for a couple of seconds. (A reminder that we are ranking his movies, and not his performances per se.) Although it was very early in his career, the blink-and-you-miss-him brevity of his appearance is a little odd; he'd been a regular on TV for some years at this point, so one suspects his other scenes were cut. And this weird seduction thriller, which helped resurrect former hell-raising child star Drew Barrymore's career, hasn't aged as well as anticipated. Still, the actress' turn as an obsessive, murderous teenage sexpot who takes over Sara Gilbert's family, is wonderfully nasty, Skinemax-style clichés or not.