Behind the Bets: Oscar Night

They can spice up the Oscar telecast all they want this year. Hugh Jackman can bust through the Kodak Theater ceiling wearing nothing but Wolverine blades on his hands and the pre-Botox version of Nicole Kidman on his back. It won't make any more people watch. Because for so many viewers these days this show is no different than a Sunday afternoon Bengals-Browns tilt. The only reason they're tuning in is to see if they win their Oscar pool.

And, I'm here to help you do just that. Along with two people who actually know something about the awards.

One is David Carr a columnist at the New York Times whose Carpetbagger blog covers Oscar season with a these-people-are-full-of-it 'tude while still taking it seriously. He also wrote a frightening (good and just plain scary) memoir (The Night of the Gun) about his largely forgotten years addicted to drugs, reporting on his past life with as cold an eye as he does the moguls he covers.

Then there's Julie Jacobs. She's an Oscar obsessive who masquerades as a completely sane mother of three boys five-and-under. She works for Watson Adventures, a company that plans adventures and scavenger hunts for corporate outings, and has an Oscar party every year that rivals Vanity Fair's (pre-downturn). She's also been the muse for her husband A.J.'s two bestselling memoirs. (I'm hoping her mojo rubs off on me.)

I chose the two of them for a couple of reasons. First, to do what the column is supposed to do: dole out some practical advice for the biggest gambling event on this weekend's calendar. And, second, to flesh out a theory I've batted around in past BTB's: In a 3G connected world, does the wiseguy provide better analysis than the square on something as heavily covered as the Oscars?

"I think expertise is widely distributed in a digital age," says Carr. "I don't think the fact that this has been my day job for four months really puts me that far head of Julie."

But even if the world is at your fingertips, you still need to tap tap tap your way to brilliance. So go ahead, fire up your iPhones at an Oscar party on Sunday and scan this conversation between the expert and the obsessive. Hopefully you can pull enough wisdom from the two of them to make a few nickels.


Mickey Rourke, Sean Penn, Richard Jenkins, Frank Langella, Brad Pitt

David Carr: When I do my final picks for all categories, I call anywhere from six to 10 Academy folks, spread out among the guilds and demographically so I'm getting some kind of very rough indication of what the other 5,800 voters think. Hopefully they tell me who they voted for, who their friends voted for and why. The why part is important, because you can sometimes pick up on some indication, some momentum or change.

Julie Jacobs: I read what people are talking about and where the early season awards are going. And then there's obviously factors like death, age, backstory. But I think the biggest thing that I consider is the history of those people, whether they have won awards or have not won awards in the past.

Carr: Sean Penn won Best Actor not long ago, right?

Jacobs: I think that's a bad thing for him because Mickey Rourke has not won, and has a great backstory. In that race it could play a factor.

Carr: I would totally agree and I think voters try and program the show a little bit, the show that they'd want to see. And they want to see Mickey up there. Those of us who cover the race constantly initially thought Mickey was going to come out of the gate and face plant.

Jacobs: Mickey Rourke's performance is great but do the voters think about the fact that going from A to B like Penn is so much more impressive than whatever feelings are evoked by watching Mickey Rourke?

Carr: I think it's much more important that Sean won recently than the fact Mickey is essentially acting out his life story. Sean's performance is great, but winning in the past hurts him.

Jacobs: After those two, I would go Brad Pitt, Frank Langella, Richard Jenkins most likely to least likely. I think Jenkins is great, honored to be nominated, great performance, but couldn't imagine him winning.

Carr: I really don't agree with your analytics. I think there is a scenario where Mickey and Sean split and Langella comes up the middle. He has done a good job out on the circuit and is an actor's actor. He comes on the screen and you go, "That's Richard Nixon." And I know there's a lot of Academy members that are thinking about that. One of the things I think about is what is going to get me ahead of my peers, the Oscar ninnies that I sort of write with and against. And this is the vote that's going to separate.

Jacobs: I'm going to go crazy and pick Mickey Rourke.

Carr: I think that's a smart choice today. But from a betting perspective, to triumph in the pool you have to predict the anomalous event, not the common event.


Taraji Henson, Viola Davis, Penelope Cruz, Amy Adams, Marisa Tomei

Jacobs: With the exception of Taraji Henson in Benjamin Button, I would not be shocked if any one of the others got picked. But that's always the case with Supporting Actress. I always feel like with this category and Supporting Actor the movies get rewarded. It's the throwaway category.

Carr: Movies or broader social concepts. I think race plays more of a role in Supporting Actor. People who want a message sent, they'll often do it in the Supporting category. And I think you're absolutely correct: Agendas can come into play in these categories.

Jacobs: I loved Marisa Tomei in The Wrestler. I really did; she really moved me. But, Viola Davis did too. It's just hard when a part is that small.

Carr: My pick is Viola and I think it's because she's got this strong single, indelible scene that sticks in people's mind. Marisa didn't knock me out. She's been that person before and I've seen it. One place where you have an advantage that I don't is I'm working the circuit and develop little crushes as I go. And I think it's one place where somebody who's not in the mix but standing back like you has an advantage. Viola's got this wonderful backstory that nobody knows, being from South Carolina, coming up through Juilliard, hacking her way in the world. Nobody knows it, nobody's going to vote on that, but I know it and I think it has an emotional impact on my picking.

Jacobs: What about Penelope Cruz?

Carr: Every time she gets near a microphone she's lovely and decent and kind and people adore her. And she is freaking adorable; let's face it.

Jacobs: It goes back to the fact that Viola has not only a great backstory and great performance, but they're going to want to reward Doubt and I think this is the place to do it.

Carr: I actually have not heard better, more solid analytics out of any person, Academy member or professional. Penelope is the leading contender. But some people, including me and you, think Viola will sneak through.


Josh Brolin, Heath Ledger, Michael Shannon, Philip Seymour Hoffman, Robert Downey, Jr.

Jacobs: If there's any lock, it's Heath Ledger. But the person who comes in second is Robert Downey, Jr.

Carr: There's only been one posthumous Oscar ever awarded; it's the guy who played Howard Beale in Network. But I think Ledger is the lock above all locks because you've got a pressing need on the part of the Academy to finish off this sort of long-running Kaddish that we've had on his behalf. Plus, regardless of whether the guy died or not, we will remember his performance for a long, long time.


Angelina Jolie, Kate Winslet, Meryl Streep, Melissa Leo, Anne Hathaway

Carr: I think that there is a clock where voters say, "No, no, no, no, yes."

Jacobs: Scorsese, The Aviator

Carr: Yes. Now it's Winslet. The Reader is a movie with a significant following on a serious topic that had some problems and didn't gain wide traction. But I think people are finding it somewhat refreshing that she's not been coy and demure. She has totally gone for it from day one. She's been quoted saying, "Yes, I want a f--king Oscar."

Jacobs: Yeah. I'm just bummed, though. I felt she was a little Hogan's Heroes in The Reader.

Carr: Ha! That is so mean. That is, like, the meanest thing anybody has said all season. Maybe the only thing meaner was someone calling Defiance something like Home for Purim with guns.

Jacobs: I loved her in Revolutionary Road. I was stunned by that.

Carr: Well, I wouldn't say this is her best role ever. I'm just … Hogan's Heroes? Come on.

Jacobs: It was the accent. There was something about that accent. And I usually buy all kinds of accents. I would love, love for Anne Hathaway to win.

Carr: It's the turn thing. It's not her turn. I did a story on her and she more or less indicated that she knew that. I fell for that role because I've been that person that shows up at a wedding and ruins everything, so I had some personal identification with it. But we're not talking about Meryl Streep, and Meryl is a threat because of her long-running relationships. She's spread the love wherever she went. People adore her and also are thrilled that she took a woman's movie, Mamma Mia, and brought it to global dominance.

Jacobs: Plus she hasn't won since like 1982, it would be like her first again.

Carr: And you've got to get this pick right, too. You got to. And if you're going with momentum, if you're going with past performance in the award season, it's Kate all the way. But you got to watch out for Streep.


Slumdog Millionaire, The Curious Case of Benjamin Button, The Reader, Frost/Nixon, Milk

Jacobs: If there's anyone who's going to beat Slumdog, it's Milk, not Benjamin Button.

Carr: Benjamin Button I don't think is going to win best picture. In spite of the 13 nominations there doesn't seem to be a lot of passionate supporters and for you to trump a favorite you've got to split votes.

Jacobs: And what's weird about Slumdog is that I don't know what it would split votes with. It really is its own world.

Carr: Yeah, it's not like last year when you had No Country and There Will Be Blood and ferocious partisans on either side. There's been none of that and, boy, it's been a little dreary as a result.

Jacobs: I'm so sure of Slumdog that I'm ordering Indian for my Oscar party.

Carr: Good plan. Meanwhile, let's get some side bets going.

Chad Millman is a Senior Deputy Editor at ESPN The Magazine, and once wrote a book called The Odds. His column takes a close look at the culture surrounding the bet.