Actor Ben Stiller and director Noah Baumbach have collaborated several times. The duo first met when in 2010 filming Greenberg, which cast Stiller as the titular character, an anxious New Yorker visiting Los Angeles who finds companionship (and more) with his brother's house sitter Florence (played by Greta Gerwig). Then the duo teamed up in 2014 for While We're Young, where Stiller plays Josh, an anxious New Yorker in a difficult marriage. Most recently, Baumbach and Stiller collaborated on The Meyerowitz Stories (New and Selected), in which Stiller plays an anxious New Yorker with a complicated family (Dustin Hoffman plays his father, while Adam Sandler plays his half-brother).

Here, Stiller explains how he first met Baumbach and Sandler, what it was like to shoot the film, and why he has always had a crush on Brooke Shields.

How you ended up in The Meyerowitz Stories?

Noah Baumbach and I became friends from doing Greenberg together. It was really interesting when we were making Greenberg. I actually lived right up the hill from where we were shooting, which was his mother-in-law at the time’s house. So, I would walk to work every day down Outpost in L.A., which nobody walks down Outpost. You almost get killed every day going to work. But Greenberg didn’t drive so it was my method way of getting into the part. But it was also kind of a goodbye to L.A. for me because I had lived in LA for 20 years and I moved to New York right after we did Greenberg. We stayed in touch, because we had a lot in common and our friends lived in New York. After that, [Noah] wrote While We Were Young, and I think he had me in mind for the part.

The Meyerowitz Stories came out of us talking about wanting to do something with Adam Sandler. Adam and I had known each other for probably 20-something years. I think I met him probably in like 1988 or 1989. Adam would make appearances on this MTV game show called Remote Control that Ken Ober hosted and Colin Quinn was on as a sidekick. It was a very popular gameshow at the time and Adam would come on and do characters. He was just starting out, and he was a really cute, popular, young standup. I was starting to try to be a director and also do sketch comedy.

Then when he did Happy Gilmore I came in and did a small part as Hal, who ran the nursing home that Happy’s grandmother stayed in. We had a great time and had talked about doing stuff over the years, but never really spent time together. Actually, doing this movie was the first time we got a chance to spend a good amount of time together. And it was just a really great experience to be able to work with him and hang out with him. I feel like we got to know each other. In a way, I feel it was sort of mirroring the relationship in the movie between Danny and Matthew who lived together for a while when they were teenagers and then they split off. And, so we kind of had the same thing where we’ve known each other but not really been together a lot.

So Adam and Noah and I got together and had lunch one day before he wrote the script and just talked about some general thoughts and ideas of what the movie could be about. I know that Noah had this idea that we’d get into a fight at one point. That was sort of like the one thing that he knew he wanted to get to before he wrote it.

And we talked about things that we’ve been going through in our lives and parents and being at a certain age where you have to deal with parents getting older and also just where you’re at in your life. And then Noah just sort of went off and wrote this very specific story that somehow we both felt very connected to, even though we only had that one conversation before.

Best Performances - 2018 - Ben Stiller
Ben Stiller wears a Gucci coat; Olatz pajamas.

Photograph by Juergen Teller; styled by Edward Enninful

What was your first audition as an actor?

I’ll tell you the cringe-y audition story I have. I had to do a monologue--it was some off-Broadway play and I was probably about 14--and it’s a kid talking about something about his bris, which is when you have the Jewish tradition of a child having his tip snipped off, right? And I went into this audition, and being the nice Jewish kid that I was, I did not know what a bris was. And I decided to pronounce it brie. BRIS as brie. So, I did the whole monologue about my bris, or like talking about this bris. It was like a drama and then at the end the guy said, “Thank you very much and it’s pronounced bris.” I did not get the part. But it stuck with me, that feeling.

And now you know the correct word.

Yeah, I thought about that all during my son’s bris. It was like, what a beautiful brie he’s having.

What was the moment you knew you made it in Hollywood?

Gosh, I would have to say mine came later in life. 10 years ago when Tropic Thunder came out, I ran into Clint Eastwood at something. And Clint Eastwood came up to me and he said he liked Tropic Thunder. That was like, for me, probably the coolest like thing ever.

Who was your first celebrity crush?

Brooke Shields. I was convinced we were gonna get married.

Had you met?

I was in New York, she was in New York. We were around the same age and we knew people who knew each other then. Eventually I did meet her. I had a friend who knew her. Like my friend’s mother knew her mother, and we did not get married. But we’re friends and friendly.

It wasn’t awkward?

Well, I never told her. Unless she sees this, she will not be aware of it. Yeah, so I had a big crush on Brooke.

Where was your first kiss?

At Hidden Valley Camp in Freedom, Maine when I was 12. It was great. It was under a tree. I remember thinking it was very romantic and cool and just like charged, which most first kisses I would imagine are.

I was at camp and I was kind of homesick. And I actually remember my father had come up to the camp because I was saying I wanted to go. And then I met the girl and then I was like, “Dad, get out of here. Get out of here.”

What was your favorite birthday?

I remember I had a surprise party when I was 30 that my girlfriend at the time threw. It was in L.A.. it was at the house that I was living in at the time, yeah. That was fun because I was truly surprised and I never had a surprise party.

How did they coordinate it? You just walked in?

My god, I don’t remember. It was so long ago. But it was like a big surprise. And there was a magician at the party. He did tricks. He did close-up magic for people. You know, like little groups of people where you come and take sponge balls out and pull things out of people’s ear.

Do you have any secret skills?

I can juggle a little bit.

Wow. Can you do magic?

I took magic lessons when I was a kid. I was really into magic. I was not very good. I didn’t practice enough. I don’t think I had the natural ability either. But there was a place called Lou Tannen’s Magic Shop in New York, which was where all the magicians went. And it was the magic shop and all the magicians would demonstrate the tricks for you there. And then you’d take them home and not be able to do them because they were magicians. But then I took lessons with this guy named the Great Slydini, who is a very famous closeup magician. He lived somewhere in Hell’s Kitchen and I would go to his apartment. I was like 10 years old, and he had this very famous routine where he would take an audience member up on stage, sit them down and he would take a box of Kleenex and crumple the Kleenex up and make them disappear in front of them. But if you were watching from the stage, what you saw was that he was flipping the Kleenex over their head, but they couldn’t see it because of their vision. It was a great routine. The audience would be laughing, the person sitting there. And, so I would be practicing this flipping the Kleenex on my sister all the time and she would just get mad and say, "why are you doing that stupid thing where you throw Kleenex at me?" She didn’t encourage my magic career. I still kind of try to do it and every once in a while I can do it.

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