45. Bob Harris 

As Seen In: Lost In Translation
Notable Sneaker:
Nike Air Woven 

Bill Murray has played so many great roles but his move as a struggling actor in Sofia Coppola's (yup, that Coppola) 2003 Lost In Translation with little purpose had us feeling sorry for homie until we caught a glimpse of his footwear. Sorry Bob, getting paid to travel first class in Wovens and whining about it kind of makes you a lame