Smiley Face (2007)

Smiley Face (2007) features a few important names: Anna Faris, John Krasinksi, Danny Trejo, Brian Posehn, and more, all probably before they reached their prime. The premise is pretty simple: Jane (Faris) finds a plateful of her roommates pot cupcakes and not knowing their pot cupcakes, eats every single one. This makes life hard, obviously, but Jane sets out to get her shit done anyway. She needs a lot of money—her dealer and her power bill won't pay themselves—and she needs to audition for another gig. Needless to say, Jane is pretty out of it the entire movie, but that doesn't deter John from jerking off to thinking about her in the shower. Somewhere along the way, Danny Masterson also fucks a skull.