RANKED: The Past 28 Oscar ‘Best Picture’ Winners From Worst To Best

28. 2002: Chicago

Chicago is one of the few Academy Award-winning films relying heavily upon song and dance. The duality of nostalgia and aesthetics makes for a truly captivating piece of art. Of course, this adaptation from a 1975 Broadway hit cannot be complete without some heavy hitters within the industry.

Director Rob Marshall/writer Bill Condon opted to go for a star-studded cast — which included the likes of John C. Reilly, Richard Gere, Queen Latifah, Renee Zellweger, and Catherine Zeta-Jones. It isn’t the typical Best Picture film — though it certainly is entertaining.

27. 1998: Shakespeare In Love

The weaving of fictional events with a non-fictional base makes for compelling art. Utilizing the famed life of playwright William Shakespeare, Shakespeare in Love is a fictional story in which Shakespeare himself (Joseph Fiennes) is experiencing many of the storylines from plays he himself has crafted. The cast is a who’s who of acting brilliance.

This in all likelihood was Gwyneth Paltrow’s best performance to date (she won the award for Best Actress). Dame Judi Dench won Best Supporting Actress in a complementary role.

Image Sources: Miramax/Movie Room Reviews, Variety