I Wonder What Olivia Wilde Was Thinking All Summer

The Friday Post.

Free me from the tyranny of Netflix trying to shove The Big Short down my throat!! New chats in the Substack app about Love Is Blind After the Altar, The Ultimatum, and RHONY.

Olivia Wilde on August 28, 2023 in Los Angeles, California. (Photo: Hollywood To You/Star Max/GC Images)

I fall into a severe melancholy every Labor Day weekend — even if summer is not technically over, this is the weekend it announces its end. This week I did not have therapy but I made do with a $7 hibiscus lemonade, just because it’s still summer. I wrote a little about this last year: “It’s still warm in September, temperate in October, reasonable (barely) in November … but there’s still so many more months until we get more summer.”

There’s one recurring thought I’ve had this summer, and I need to reach some sort of closure now that it’s summer’s season finale: What was Olivia Wilde thinking all summer? This summer’s biggest movie was about a beautiful woman breaking out of her utopia that was actually something of a gilded cage (and the men who wanted to run that utopia); this summer’s most internetty movie is the story of two unpopular best friends who try to make high school just a little more bearable, and cleverly usurp the raunchy Judd Apatow comedies in the process. I’m talking about Greta Gerwig’s Barbie and Emma Seligman’s Bottoms, of course, but do those descriptions not also apply to Wilde’s two directorial efforts Don’t Worry Darling and Booksmart?

This time last year we were in the throes of Worrying, Darling: Harry Styles was on tour, but was about to go to Venice for the movie’s premiere. The fallout between Wilde and her star Florence Pugh was public, and Pugh would memorably skip the DWD press conference to wear Versace and drink and Aperol spritz. Chris Pine would look bored through all of this, of course, and let us not forget spitgate. This year, by contrast, Wilde has laid low, mostly getting papped leaving the gym and posting about the WGA/SAG-AFTRA strikes.

Just indulge me: I have to know what she is thinking! I liked Booksmart more than a lot of people did, but the alt-comedy strain of Bottoms out-weirds it. Don’t Worry Darling wanted to say everything Barbie said, but in Harry Styles’s not quite British but also definitely not American accent. Is it like the Saturday Night Live Sarah Palin-Hillary Clinton sketch, where Hillary Clinton is indignant, watching someone else live out her dream? (“I didn’t want a woman to be president, I wanted to be president!”) Or is Olivia Wilde very blase about it all, simply charging forth into the next project, on which we can assume she will have a no asshole policy? Privately, in a whisper, is she like Don’t Worry Darling ran so Barbie could soar? Or, at the very least, she cast Florence Pugh as “dream girl,” to which Christopher Nolan added the “manic pixie?” Devoted Hung Up readers will recall that I, improbably perhaps, love this bitch. I simply must know what’s going through her head.

Speaking of summer being over: and now his watch is over. Leonardo DiCaprio’s brief foray into elder outreach — dating a woman over the age of 25-and-a-half — appears to finally be done. He has served his time with the living dead, the geriatric late-20s crowd. Gigi Hadid went to a house party with a music producer named Cole Bennett, according to Elle. The Daily Mail spotted Leo at LAX, once again with the Italian model Vittoria Ceretti.

Gwynterogation
I know that everyone is tickled by Gywneth Paltrow’s uncanny ability to be approachably out of touch — no one is doing it like her! — but I have not seen enough attention paid to this random person’s query. “I’m asking this everytime answer the question” … what a way to talk to someone! Whatever happened to class… etc.

Paltrow’s answer was divinely blunt: “Oh my god stop yelling at me! I didn’t, I just, it just — we just stopped doing it because Iron Man died, and why do you need Pepper Potts without Iron Man? I don’t know!” Mind you, she barely remembers she’s in these movies, which is really the way it should be. “Call Marvel and yell at them, not me,” Paltrow concluded. “I’m just sitting here.” How dare you interrogate her!

That’s all this week! Thank you for reading. Despite the Weeknd’s best efforts, HBO canceled The Idol. Guess it wasn’t “Popular.” Have a good weekend!