6) The Minus Man (1999)
Before Owen Wilson was typecast as the all-charming romantic comedy foil to Vince Vaughn, he was tackling riskier roles, like 1999’s The Minus Man. In this thoroughly oddball thriller, Wilson plays a drifter (Vann) with an appetite for murder who makes a habit of poisoning his victims and walking away scot-free.
Vann’s methods are simple: he doesn’t kill people he knows, and he doesn’t kill people near home. But when he violates the second important rule he implicates his neighbors in his web of destruction, one of whom is played by the inimitable Brian Cox.
With stellar writing and a great cast (Dwight Yoakam is one of many awesome actors), The Minus Man is an ensemble showing and a rare opportunity for Wilson to display a different set of skills. Granted, he’s the same laid-back guy we see in his romantic comedies, but with an added edge. Ironically, Wilson is perfect for the part, as his unassuming demeanor and softly-spoken character mark him out as a chilling sociopath.