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2. Alan Ruck in "Ferris Bueller's Day Off"
Aww. Poor Cameron Frye. The long-suffering (from his allergies, his dad, his secret crush on Sloane Peterson ...) best friend of Matthew Broderick's iconic teen character always seemed like a grumpy old man at heart. Which makes sense, considering he was 29 years old playing a junior in high school. Ruck continues to kick it old-school, er, new -school, enjoying more age appropriate roles in TV's "Greek" as Dean Bowman and the recent high school flick "I Love You, Beth Cooper" as Mr. Cooverman.