10. Monster (2003, Jenkins)
It may seem a little off to start this list with a film about a serial killer, as that may not be considered an especially positive portrayal of a lesbian. But I think the film handles that particular aspect of Aileen Wuornos very well, as merely incidental and not directly related to her mental instability, and just in general, the film actually paints a fairly sympathetic portrait of her character (almost to a fault, honestly). The most important thing about the entire movie, though, as far as I’m concerned, is that it boasts an incredible scene of Wuornos and Christina Ricci’s character discovering their lust for one another in a roller rink, set to Journey’s epic Don’t Stop Believin’, which is easily one of the most romantic love scenes ever put to film. Click here to watch the scene on youtube.