18. JOHN CUSACK AS U.S. MARSHALL VINCE LARKIN IN CON AIR (1997)
In this case, we’re calling out the wrongful casting simply because we like John Cusack so much. Since his iconic coming-of-age ’80s movies, the eclectic actor has bettered damn near every project he’s taken on, including the ridiculous 2009 CGI-orgy 2012. Back in 1997, Cusack was respected but not quite a mega-star, so perhaps he joined director Simon West’s moronic yet shamefully enjoyable Con Air in hopes of gaining a whole new popcorn-flick-loving audience. Unfortunately, seeing Cusack actually trying to act out an idiotic script and distract viewers from Nicolas Cage’s long hair and bad Southern accent turned out to be a painful experience.