The Young Philadelphians (1959)

Ostensibly about the life and times of one Anthony J. Lawrence, played by Paul Newman, the supporting characters bolster a story of an entire generation of young Philadelphians and themes on history repeating itself and fighting against the expectations of others. Also featuring Robert Vaughn, an aged Brian Keith, and small roles by Billie Burke and Adam West, I really dig any film that ends with a trial featuring a wily defending lawyer.

Oscar Nominations: Best Actor in a Supporting Role; Best Cinematography, Black-and-White; Best Costume Design, Black-and-White