Dear Gossips,

Every year, Peggy Siegel, publicist, event planner, award season strategist, publishes her Oscar week diary. In 2016, when Leonardo DiCaprio won Best Actor she revealed that a year earlier, he’d asked her,  “When am I going to win? I’ve had four nominations.”

It was a delicious little anecdote – because, of course, Leo probably doesn’t want you knowing that he goes around asking people those kinds of questions. Leo never wanted it that bad, OK?

Come on. They all want it that bad.

It’s been a month since the Oscars, a month since The Accountant that wasn’t Ben Affleck f-cked up the envelope. Peggy Siegel has shared her Oscar diary with Avenue. This time both Damien Chazelle and Barry Jenkins ask her if they’re winning Oscars. And all week people kept asking her who and what would win the Oscar. Not that we didn’t know how much Hollywood cares about the Oscars. But I always appreciate the reminder since they spend so much time pretending that they don’t.

Peggy doesn’t pretend though. She cares so much. And she still cares that she didn’t see it, didn’t see that Moonlight would upset La La Land for Best Picture. She talks about how she missed all the signs. And then, as soon as she arrived at the Dolby that night, she ran into another publicist who basically told her, point blank, that it would be Moonlight. Which she hilariously shared with one of the producers of La La Land who promptly “turned white”. Which pissed off Lisa Taback, one of the top Oscar campaign strategists in the business. Lisa Taback handled the Oscar-winning campaigns for Spotlight and Room in 2015/2016. Before that she worked on The King’s Speech and The Artist. And she was in charge of La La Land’s Oscar campaign. You’ll recall, Jennifer Aniston also hired her when she was pushing for an Oscar nomination for Cake. Still, this is Hollywood inside baseball. By and large, most people don’t know that that’s how Oscar season works. Or they don’t want to believe that that’s how Oscar season works.

I know you don’t want to talk about Oscars for another six months, at least. But… in Hollywood, conversations about Oscar 2018 have already started. Like did you know that Daniel Day-Lewis and Paul Thomas Anderson are currently shooting a new film in London about the world of couture in the 1950s? Whenever DDL does anything it ends up being Oscar-related. The last time DDL did something with PTA, it resulted in There Will Be Blood. The film doesn’t yet have a title but they’re saying it could be ready this year. 

Also… Justin Timberlake might be back at the Oscars in 2018, God help us. Footage from Woody Allen’s Wonder Wheel will be presented at CinemaCon tomorrow. JT is in the movie with Kate Winslet. Kate Winslet’s on the early list of Oscar Best Actress potentials. So prepare yourself emotionally for JT’s enormous ego once again attempting to dominate that event.

Click here to read Peggy Siegel’s 2017 Oscar diary.

Yours in gossip,

Lainey