6. Sleepwalk With Me (2002)
Sleepwalk with Me is a bit different from the other ones on the list because it is about relationships and the nature of romance instead of boy chasing after girl (and vice versa). Sleepwalk with Me is written and directed by the star of the movie, comedian Mike Birbiglia. It is his real life account of him dealing with sleepwalking that was induced by stress. That stress stems from him struggling to be a comedian and the pressure he feels from his family to marry his long-term girlfriend Abby (Lauren Ambrose). While this movie doesn't follow the traditional romantic comedy story, it does have some interesting perspectives on relationships. What it is like to go from a single person to a couple. Seeing the relationships of those around you and the disasters that they are; do you really want to get to be that way with someone you love? Sleepwalk with Me gives more questions than it answers, but it's still one of the funniest movies on the list.