Almost There: Christopher Plummer in "The Insider"
Despite starring in two Best Picture winners and many other movies blessed by plentiful love from AMPAS, Christopher Plummer always struggled to be recognized by the Academy. While the actor earned a lot of golden accolades and nominations for his TV work, including two Emmys, his cinematic efforts rarely caught the attention of awards-giving bodies. It was only in the twilight of his career that such fate changed but that doesn't mean he wasn't deserving before. For example, in 1965, the year of The Sound of Music, I'd have happily nominated him both for his stern star turn as Captain von Trapp and for the malicious sensuality he brings to Inside Daisy Clover.
Still, the closest he ever came to an Oscar nomination pre-2009 was for Michael Mann's The Insider...