
Oscars flashback: Clint Eastwood leads the way
In any given year, what makes for a best picture? Are there clues as to what might win, strewn throughout any given Oscars broadcast? As a matter of fact, there usually are — at least if you know what to look for: a sweep, a director win or even a chance to make history. Still, at the 77th Academy Awards ceremony, held Feb. 27, 2005, at the Kodak Theatre in Los Angeles, 'Million Dollar Baby' was not a lock on the prize — until all at once, it was.
Over the last 20 years, guessing how voters will choose the best picture frequently comes down to a few factors — the most obvious being if the director wins ahead of the best picture prize. Since the 2005 awards, 13 best picture winners also had directors who won that night. Still, that's no guarantee a best picture contender will even have a director nominee.
For a time, there was a run of director-best picture parallels — between the 2005 and 2011 awards — that made the two biggest prizes of the night seem intertwined. Clint Eastwood kicked that stretch off by earning his second directing award and second best picture win for 'Million.'
The presentation was a fantastic bit of Oscar history. First, Eastwood, along with fellow producers Albert S. Ruddy and Tom Rosenberg, accepted the award from presenters Barbra Streisand and Dustin Hoffman. 'I'm so happy to give this to you again, Clint,' she said after opening the envelope — telling the world that not only had he won tonight, she'd been the one to present him with his first directing Oscar in 1993, for 'Unforgiven.'
Then Eastwood had his own flashback to recall: This was Ruddy's second (and final) Oscar, his first being for 'The Godfather,' which he accepted at the 1973 awards from … Clint Eastwood.
'[E]very time I started going to this [awards ceremony], I'd say, 'I'm going to enjoy myself whether I win or lose,'' Ruddy (who died in 2024) told the audience. 'But believe me … it's better to win! I love it.'
Ruddy gave thanks to his family, the cast of 'Million' — Eastwood, Morgan Freeman and Hilary Swank — then also thanked Anjelica Huston, who'd introduced him to the works of F.X. Toole, the author of the short story that inspired 'Million' screenwriter Paul Haggis. He added, 'I'm going to sit down and get a piece of lemon pie with the real filling, I'm going to look at this, and then I'm going to die and go to heaven.'
Along with his directing Oscar in 1993, Eastwood also won best picture for 'Unforgiven' that year too. He has one other Oscar, for the Irving G. Thalberg Memorial Award from 1995. This was Rosenberg's first nomination and only win thus far. 'Million' also took home the lead actress award (Swank) and supporting actor (Freeman).
The remaining films on the nomination slate included five-Oscar winner 'The Aviator,' whose director Martin Scorsese was not included as one of the nominated producers. Those were Michael Mann, who has four nominations and no wins; and Graham King, who would take home his first Oscar in 2007 when Scorsese's 'The Departed' won best picture.
One-time Oscar winner 'Finding Neverland' had two producers: Richard N. Gladstein and Nellie Bellflower. This was Bellflower's only nomination thus far; and Gladstein's second. 'Ray' (which won two Oscars) director Taylor Hackford has one win for live-action short film; and his co-producers, Stuart Benjamin and Howard Baldwin, received their first nominations with 'Ray.' Michael London, who produced 'Sideways,' also received his first and so far only nomination on this evening.

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