We’re taking a trip back this week to some of the darkest days in the “Get Leo an Oscar” saga: Clint Eastwood’s J. Edgar. The film starred Leonardo DiCaprio and detailed the many political exploits of J. Edgar Hoover and his efforts to stomp out communism. The actor would get close to a nomination (after showing up for the precursor triple crown of Globes, SAG, and Critics’ Choice) but this prestigious biopic was not meant to be for Leo and his eventual Oscar. What didn’t help the film’s case were many unfortunate elements aside its anemic box office: a wishy-washy take on Hoover’s tyranny, DiCaprio sobbing in a muumuu, and most notoriously, its laughable old age makeup. This episode, we discuss Eastwood’s overly expeditious tendencies, screenwriter Dustin Lance Black, and the film as a turning point for supporting costar Armie Hammer. And to spread some goodwill, this week we also discuss favorite performances from J. Edgar’s most cast-aside ensemble member: the one and only Naomi Watts. Follow Us on Twitter! @Had_Oscar_Buzz Joe: @joereid Chris: @chrisvfeil