Which Oscar looser wins first?

I've dug Brad Pitt in most everything I've seen him in, especially 12 Monkeys, and Johnny Depp is my favorite actor and Clooney is No. 2, so the pretty boy thing isn't an issue. Something about Leo just hasn't sat right with me since Titanic. I thought he was great in Basketball Diaries and What's Eating Gilbert Grape? I haven't seen The Departed yet, maybe when I do that'll change things for me.

 

Check out "Catch Me if You Can"....I think that was one of DiCaprio's best performances...he was certainly better in that than "Gangs of New York"

 

Christ, thank you. I knew I had recently seen him in something I liked but couldn't think of it. I actually really liked Gangs of New York but thought Catch Me was kind of meh. I enjoyed it the one time I saw it but haven't found it rewatchable.

 

O'Toole already has a lifetime Oscar to his credit.

As for Whitaker, knowing how much of a shoo-in he was to win, wouldn't it have been great to see how "Jefferson" would have reacted if he'd lost?

Jefferson ... tackle by Jefferson ... QB sack by Jefferson ... Jefferson ...

Spicoli, I mean Sean Penn could have defended his actions like he stood up for Jude Law!

 

Hey, he was outstanding in that recent McDonald's commercial!

 

Was Whitaker considered a sure thing?
Our critic didn't think he would win because he's not the actual lead actor in the movie.
I don't know. I haven't seen it.