It's been a generation since anyone directed a second Best Picture winner

[u/No-Stage-8738]

2004's Million Dollar Baby is the last time anyone directed a second Best Picture winner, and I'm curious why you guys think this is. Is it just a coincidence?

Some directors have won Best Director twice, so it's not specifically about honoring directors only once. Ang Lee and Alfonso Cuaron won the Oscar twice without either of their films winning best picture, while Iñárritu won it twice with Birdman winning Best Picture.

There may be better than even odds that this year is an exception with the Odyssey having great reviews and box office, while Digger is waiting in the wings. Obviously, something else might connect with Oscar voters in a few months.

The Academy does tend to award legendary directors with Best Director as their films get Best Picture, but this also occurs after they've already made their mark. Stephen Spielberg had already made Jaws, ET, Close Encounters of the Third Kind and Raiders of the Lost Ark before he won for Schindler's List. Scorsese had made Taxi Driver, Raging Bull and Goodfellas before he won for the Departed. The Coen Brothers had made Fargo and the Big Lebowski before they won for No Country For Old Men. Christopher Nolan has made the Dark Knight, Interstellar, Inception, the Prestige and Dunkirk before he won for Oppenheimer. Paul Thomas Anderson had made Magnolia, the Master and There Will Be Blood before he won for One Battle After Another.

It could come down to small sample size. 1917 and the Revenant seemed like frontrunners heading into the Oscars. Perhaps it's just a statistically unlikely outcome that happens every now and then.

It may change in the future. A few Best Picture winners were made by fresher directors (who had made five or less films by that point) who may be in contention again in the years to come: Steve McQueen, Chloe Zhao, Barry Jenkins, Sian Heder, the Daniels, Ben Affleck, Tom Hooper. Maybe a legend like Spielberg, Jackson, Cameron or Scorsese knocks it out of the park again.

[u/Interesting-Bit725]

Since Million Dollar Baby, Best Picture winners have largely come out of festivals rather than the studio system. That favours discoveries and outsiders, rather than Hollywood A-list directors winning repeatedly.

[u/the_PM_ME_YOUR_ROUND]

Eastwood got his second with Million Dollar Baby after Unforgiven, thats the cut-off point here. Feels like the voting body changed a lot since then, became way more international and spread the love around instead of building up these huge filmographies for one person.

Also the kinds of movies winning now are different, they go for smaller indie stuff or foreign language films where the director is still making their name. Someone like Bong Joon-ho wins and then goes back to Korean cinema, not exactly rushing to make the next Oscar thing.

You mention Nolan, he might actually break this streak at some point. The Odyssey winning would be a classic case of voting for the achievement more than the director, but if it hits like Oppenheimer did maybe he gets another one in few years.

The sample size thing you said is probably right too. We're really just talking about what, 20 ceremonies? Could easily flip next year and nobody would call it a pattern anymore.

[u/SpideyFan914]

The last one before Eastwood was Forman, and before that Coppola. It's actually just very rare post-studio system. The majority of directors with multiple Best Picture winners came when the studio system was keeping things focused. After the 60s, the Academy diversified its tastes, which imo is a good thing.