8 Terrible Films That Somehow Won The Best Picture Oscar

4. Chicago

Year: 2002 Fellow Nominees: Gangs of New York, The Hours, The Pianist, The Lord of the Rings: The Two Towers Another year, another spectacular oversight from Oscar, who somehow gifted Rob Marshall's anodyne Chicago with a Best Picture award in the same year that Roman Polanski released an absolute masterwork in The Pianist. Also sitting at joint-second all-time with thirteen (sigh) Oscar nods, the film, based on Cabaret director Bob Fosse's book, was the first musical to win Hollywood's top honour since Oliver! in 1968. How exactly it managed to do so in a year when Roman Polanski and Martin Scorsese both had huge movies nominated, and when the second instalment of The Lord of the Rings was nominated, and when the critical darling that was The Hours was nominated, is a different matter entirely. Marshall thankfully lost out on Best Director to Polanski, but that didn't stop Chicago from winning six Oscars on the night, mostly technically ones bar Catherine Zeta-Jones' pretty surprising win for Best Supporting Actress. A well designed film (you can't really argue with its wins for set-design or art-direction), Chicago is otherwise a bit of an embarrassment as a Best Picture winner; good in its musical moments, yes, but ultimately a piece of pop fluff in comparison to some of the major concertos it was nominated with.