13Scott Coffey - Ray
Scott Coffey already had a connection to John Hughes when he was hired to play Ray, the edgy kid who tries to put the moves on Watts after she uses him in an effort to make Keith jealous. The actor had a small role in Hughes' Ferris Bueller's Day Off.
Coffey didn't get a lot of screen time in SKOW, but he made the most of it, getting laughs with one of the movie's best punchlines. Watts tells Ray that it's 1987 and "a girl can be whatever she wants to be." His straight-faced reply: "I know. My mom's a plumber."
Coffey did a lot more supporting parts after his time as Ray. You may have caught him in stuff as diverse as Wayne's World 2, Tank Girl, and David Lynch's Mulholland Dr. He still acts occasionally -- he'll be in the upcoming Twin Peaks revival -- but these days, you're more likely to find Coffey behind the camera. His first effort as a writer/director was the 2005 indie comedy Ellie Parker, starring Naomi Watts and Chevy Chase. His second was 2013's Adult World, with John Cusack, Emma Roberts, and Evan Peters.