Jake Gyllenhaal and Sister Maggie Were “Traumatized” By Their Homemade Halloween Costumes Growing Up

Theirs were... special.

Jake Gyllenhaal is an actor who puts a lot of meaning into his physical transformations. Think of his most memorable roles and you’ll remember how he looked: his Marines torso in Jarhead; his rippled boxer in Southpaw; his reedy desperation in Nightcrawler. In Stronger, his latest demanding role, Gyllenhaal plays another character whose bodily challenges once again give shape to his mental and emotional ones—the real life Jeff Bauman, who lost both of his legs during the Boston Marathon bombings in 2013. Here, Gyllenhaal recalls to W editor at large Lynn Hirschberg both the inspirational lessons he learned spending time with Bauman, and the terror of letting his artsy father make his Halloween costumes growing up.

Tell me about Stronger. How did the part come to you? Stronger is the story of Jeff Bowman, this really incredible man who happened to be at the wrong place at the wrong time in a lot of ways—he was there waiting at the finish line for his girlfriend, who was running the race, during the Boston Marathon bombings. And I came across this piece of material in a very early stage, in a very early draft, and I just fell in love with the character of Jeff, ’cause he has this incredible sense of humor. Through all of it, the inexplicable and impossible pain, comes this sense of triumph because of his sense of humor, and, you know, I think he even surprises himself. His life is just a huge inspiration.

What was the hardest thing about making the movie. Was it the physical challenge? No, in a lot of ways, I feel like the hardest thing was trying with every bit of myself to get anywhere near understanding the sort of emotional, mental journey that Jeff went through, which I knew I would never really be able to do. I was going into this journey knowing I was probably going to fail. And it was sort of interesting, you know, knowing nothing I was gonna do was gonna touch what he went through. So, the hardest thing was sort of knowing that about myself, doubting myself constantly, and playing a character where you are pretty much unsure all the time, which I then discovered was really sort of a similar way to the way that Jeff felt.

That’s beautiful. It is. You know, I think people use words like light and dark, you know, you need to know pain to know joy. He is the personification of that. If he were here with me now, his light would overwhelm. I’d have to wear these [sunglasses].

[Laughs] Well, that’s the ultimate compliment, really. I mean, he deserves it. He’s the kind of guy who will stay up with you till 3:00 or 4:00 a.m. talking. Actually, I was texting with him last night around midnight, Los Angeles time, and he was still up, talking with Kevin, his boss at Costco, who’s been one of his best friends. They were talking for, like, four hours, just about life and stuff.

It’s nice that you get to be friends, and that you learn so many things from each movie. I mean, you started boxing for Southpaw, you drove around with cops for End of Watch. It’s always good to be friends with the cops.

When you play a cop, are cops nicer to you when anything happens? Um, I don’t know anything about that… I get the kind of, you know, unspoken nod. I actually recently, unfortunately got a speeding ticket, which I was like, “Watch this, it’s cool. I got this.” The [officer] was like, “License, registration, please.” And I was like, “But I mean, buddy.” He was like, “License, registration.” I was like, “I played a cop.” He’s like, “Go f— yourself.” [Laughter.] So that didn’t help. But yeah, at least I get the nod. At least I get the nod. I still got the f—ing ticket, but I got the nod.

Some fun questions now: What was your favorite Halloween costume? Well, it’s a toss-up. My favorite one I ever wore was no Halloween costume, because essentially that’s my job—to just dress up like almost every day is Halloween. Which I’m always surprised by, when actors are excited about Halloween. They live it every day.

Jake Gyllenhaal in “Stronger

My dad always told me, “The job of an artist is to disturb the comfortable and comfort the disturbed.” That’s always in my mind. It’s why I’m attracted to projects that are maybe going to illuminate something to you about yourself. It’s always a little frightening because you don’t know what you’re going to discover.

Pringle of Scotland jacket; Frame T-shirt.

Photographs by Juergen Teller; Styled by Edward Enninful

You’d be surprised. Maybe I was just traumatized by my costumes that my dad helped me create when I was a kid. I was like an Ocean Spray cranberry juice box that was made out of… my dad apprenticed with Red Grooms, the artist. He designed all these really outlandish things made out of cardboard for Halloween that I wore, and were torturous. He made a house, and the house had rooms in it. They were all lit up by Christmas lights, and each one had a different scene, like one scene where people, like, fighting, and the other one was someone was reading to a child, and there’s all these people eating dinner downstairs. And the house fit on top of my head, and I could look out one of the windows. And then the chimney was where you put the candy, right? So, I wore it on my head, and then I had a backpack with a battery pack, no joke, that lit up all the lights in the house. But I couldn’t move my knees farther than maybe three or four inches, so very time I would walk, my knees would hit the front of this thing. On my way upstairs to get candy, I would fall flat over; I wouldn’t really know where I was going.

And no one could really hear me very well, so when I would ask people for candy, they’d be like, “Sorry, excuse me, trick-or-treat.” I’d be like, “Treat.” And it’d be like [muffled noise]. And they’d be like, “What?” They’d be like, “Where do we put the candy?” And my dad would be sitting there like, “Let’s see if they know.” Occasionally they’d just give up, and I’d be left there with the door closed. The chimney thing didn’t work out. I was freed like 30 or 45 minutes into it. My dad was like, “I can’t do that to you.”

How old were you? I think I was, like, 10 or 11.

Oh my god. So they never let you be, I don’t know, a superhero or a ghost? No, no. Like, my sister was like an Oreo cookie one year, made out of foam. My dad cut out all the pieces; it was beautiful. She wore white spandex, and they draped the thing over her shoulders.

That seems more mobile. Well, I think I was, like, Elvis Presley one year. That was fine. My sister dyed my hair with Manic Panic. It was awesome.

How long did that last? Forever. Like, someone asked me the other day why am I an actor, and the answer was because Manic Panic had its way with my brain probably. I don’t know.

I used Manic Panic. It lasted way too long, though. Way too long, and it just stays forever. It looks like chlorine in your hair after too much time. When are you gonna ask the fun questions?

[Laughs.] These are the fun questions. Where was your first kiss? Um, it’s debatable. In the stairwell in elementary school. Yeah, the door closed and we, like, we kissed.

During school? Yeah. Her name was Kyla. Yeah.

Good name. I know. It was a peck. The first real one was outside a bowling alley. It was a birthday party of a friend of mine. I didn’t even know it was gonna happen. We were talking outside, and she sort of made the first move. I remember that. I was, like, “This is the beginning of the end.”That was, “Wow.” It was wonderful, yeah. I remember asking my grandfather about when he first kissed my grandmother. He closed his eyes, he said, “Glorious.” Like that.

Have you gotten great advice from your dad? Yeah, my dad said something to me, I’ve said it a lot, but in terms of work, he’s always said that the job of an artist is to disturb the comfortable, and to comfort the disturbed. That’s always in my mind.

That’s great. Do you try to do things that scare you? I don’t know if I try, but I’m attracted to those things creatively. You know, you move towards those things that ask something of you that are gonna maybe illuminate something to you about yourself, and I think that’s the reason why I do what I do. So, that’s always a little frightening, ’cause you don’t know what you’re gonna discover. That’s what I about my job. It’s not scary. That’s exciting to me.

Do you have a secret skill? I mean, I do other things. I mean, but um, I mean, there are probably a lot of secret skills.

You know what you’re good at? You’re good at training dogs. I am good at training dogs. My dog is very well-behaved, and, but also very well-loved, which I guess is a part of having them behave well, too. I love dogs. I just love them. I don’t know what to say about that, except like meeting your dog, they are so playful. The first interaction everybody always has with a dog is, like, “Oh, hi. Well, hello. Oh, you know, like, so nice.” And pet. But then, all they wanna do really is play. They bring that out in us if we allow it. That’s what I like about dogs, because I don’t think I’m that playful, generally. I need to be reminded, so they remind me.

Gal Gadot, Emma Stone, Margot Robbie, and More Are the Best Performances of the Year

Jennifer Lawrence wears Dior dress; Dior Fine Jewelry earrings, and ring. Beauty: Dior. Emma Stone wears Louis Vuitton dress. Beauty: L’Oréal Paris.

Photographs by Juergen Teller. Styled by Edward Enninful. Set design by Peter Klein at Frank Reps. Hair for Lawrence by Jenny Cho at Starworks Artists. Hair for Stone by Mara Roszak at Starworks Artists. Makeup for Lawrence by Genevieve Herr. Makeup for Stone by Rachel Goodwin at Streeters. Manicures by Michelle Saunders for Essie at Forward Artists.

Gal Gadot wears Giorgio Gadot wears Giorgio Armani jacket; Fabergé necklace; her own earring. Beauty: Revlon. James Franco wears Giorgio Armani jacket, shirt, and bow tie.

Photographs by Juergen Teller. Styled by Edward Enninful. Set design by Peter Klein at Frank Reps. Hair for Gadot and Franco by Yusef for Rich Hair Care at Factory Downtown; Makeup for Gadot and Franco by Fulvia Farolfi for Chanel; Manicures by Michelle Saunders for Essie at Forward Artists.

Daniela Vega wears Salvatore Ferragamo dress; Tiffany & Co. earrings; Gianvito Rossi shoes. Beauty: Covergirl. Robert Pattinson wears Dior Homme tuxedo, shirt, and bow tie.

Photographs by Juergen Teller. Styled by Edward Enninful. Set design by Peter Klein at Frank Reps. Hair for Vega and Pattinson by Yusef for Rich Hair Care at Factory Downtown; Makeup for Vega, Pattinson by Fulvia Farolfi for Chanel; Manicures by Michelle Saunders for Essie at Forward Artists.

Marbot Robbie wears Louis Vuitton dress; Wing & Weft Gloves gloves. Beauty: Lancôme. Nicole Kidman wears Dior dress; Wing & Weft Gloves gloves. Beauty: Neutrogena.

Photographs by Juergen Teller. Styled by Edward Enninful. Set design by Peter Klein at Frank Reps. Hair for Robbie by Yusef for Rich Hair Care at Factory Downtown. Hair for Kidman by Mara Roszak at Starworks Artists; Makeup for Robbie by Pati Dubroff at Forward Artists; Makeup for Kidman by Fulvia Farolfi for Chanel; Manicures by Michelle Saunders for Essie at Forward Artists.

Tom Hanks wears Tom Ford suit; Emma Willis shirt; Hanks’s own jewelry. Mary J. Blige wears Versace dress; Chopard earrings; De Beers ring. Beauty: MAC Cosmetics.

Photographs by Juergen Teller. Styled by Edward Enninful. Set design by Peter Klein at Frank Reps. Hair for Blige by Randy Stodghill at Opus Beauty; Makeup for Blige by D’Andre Michael; Grooming for Hanks by Barbara Guillaume at Forward Artists; Manicures by Michelle Saunders for Essie at Forward Artists.

Saoirse Ronan wears Chanel dress; Tiffany & Co. earrings; Jimmy Choo pumps. Beauty: Chanel. Andrew Garfield wears Prada suit and top; Converse sneakers.

Photographs by Juergen Teller. Styled by Edward Enninful. Set design by Peter Klein at Frank Reps. Hair for Ronan and Garfield by Yusef for Rich Hair Care at Factory Downtown; Makeup for Ronan and Garfield by Fulvia Farolfi for Chanel; Manicures by Michelle Saunders for Essie at Forward Artists.
Photographs by Juergen Teller; Styled by Edward Enninful

“This year on Halloween, my daughter and I went trick-or-treating, and I had on this huge mask so I could see everyone but they couldn’t see me. Whenever I saw a Wonder Woman costume on a girl or a boy, it was so exciting. My daughter, who was dressed as a unicorn zombie, would run up to me and say, “Did you see that Wonder Woman?” They were everywhere!”

Gal Gadot wears Moschino Couture dress; Fabergé ring; Off-White c/o Jimmy Choo shoes.

Photographs by Juergen Teller; Styled by Edward Enninful

“[Jennifer Lawrence] came to see Cabaret and both of my contacts popped out of my eyes at the same time and my prescription is -900, which, if you know what that means, is like…I cannot see. So, they had to drag me off the stage in the dark and she came backstage afterwards and I was like, ‘I couldn’t see anything! It was garbage! It was a disaster!’ And she was like, ‘Enough, enough. I’m your dance mom. You need to calm down.’”

Emma Stone wears a Louis Vuitton dress; Cartier earrings.

Photographs by Juergen Teller; Styled by Edward Enninful

“I am Vietnamese, and we don’t celebrate birthdays. My parents don’t actually know their birth dates—they just go by their signs. When somebody asks you how old you are, you say, ‘I’m born this month in the Year of the…’ I was born in the Year of the Sheep. Sheep don’t like to be the center of attention, and they don’t like being told what to do. That pretty much sums me up.”

Hong Chau wears an Etro dress; Chanel Fine Jewelry earrings; Tiffany & Co. ring.

Photographs by Juergen Teller; Styled by Edward Enninful

“I’ve had a flirtation with Winston Churchill for years; there’s been a book of famous Churchill quotes on my bookshelf since childhood. To me, he was the man who won the war. And yet, when I was first asked to play the part, I thought, Don’t be ridiculous, and turned it down. But they came back, and it felt right. My wife said, ‘Look, you get to stand in Parliament and say these great words. What have you got to lose?’”

Gary Oldman wears a Canali suit; Boss shirt and tie.

Photographs by Juergen Teller; Styled by Edward Enninful

“I always joke that Jason Dixon, the character I play in Three Billboards, is Barney Fife meets Travis Bickle. I spent a lot of time trying to perfect his southern Missouri accent. I did ride-alongs with a cop down there—he had a great twang. Accents should be practiced as if you’re drunk. Actors get a little tense when they have to do an accent. Drunkenness relaxes everything.”

Sam Rockwell wears a Marni trench; Editions M.R shirt; Simon Miller T-shirt; Huntsman pants; Rolex watch; Church’s shoes.

“My character in The Meyerowitz Stories is a sweet family girl, but when she sends films she makes in school to her family, you see her wild side. I’m naked in most of those films. I sat next to my dad at the premiere, and that was probably the most uncomfortable thing in my life. To see myself 75 feet tall and naked was not easy. I sank into my chair and heard my dad kind of laugh nervously. We pretended those scenes never happened.”

Grace Van Patten wears an Alberta Ferretti dress; her own jewelry.

Photographs by Juergen Teller; Styled by Edward Enninful

“Being an actress, for me, is about my own transition. It’s about looking for answers. It’s about trying to survive in my life and also for the lives of others who face similar challenges. Life is scary, but art is not scary.”

Daniela Vega wears a Max Mara dress; David Webb earrings; Piaget necklace; Chanel Fine Jewelry ring (right hand); Tiffany & Co. bracelet and ring (left hand); Gianvito Rossi shoes.

Photographs by Juergen Teller; Styled by Edward Enninful

“My husband is an artist, but he still has a hard time watching me sometimes. During The Killing of a Sacred Deer at the Cannes Film Festival, he was both hypnotized and shattered. When he hears me scream or cry from a certain place in my soul, it’s almost like it goes straight into him. His brain and heart don’t discern between acting and real life.”

Nicole Kidman wears a Prada top and skirt; Chanel Fine Jewelry ring; Jimmy Choo pumps.

Photographs by Juergen Teller; Styled by Edward Enninful

Where was your first kiss? This is going to sound like a murder story, but it was in the woods, outside of a baseball park. I had lost my turtle. Curtis, the guy I kissed, found it.

Was that your first pet? No, it was a schnauzer named Ozzie. He hated us so much. He never wanted to be in the same room with us.

So what’s your porno name—first pet plus first street name? Ozzie Ormond.

What was your favorite Halloween costume? A picnic table. My mom wouldn’t let me be a witch or a ghost or anything demonic, so I cut a hole in a plastic cloth and went as a picnic table. The problem was I had a crush on this guy named John, and I was so pumped for Halloween because it was our chance to interact. And then I put my face in the tablecloth and was like, “Hi, John. Are you my boyfriend?”

Jennifer Lawrence wears a Dior dress; Dior Fine Jewelry earrings and ring.

Photographs by Juergen Teller; Styled by Edward Enninful

“When I first read the script for Get Out, I thought, Are you allowed to do this? Are they really going to let this black guy kill all these white people? I think the most fascinating art pieces come at a price to the person making them. And this movie took a risk. On opening night, I went to see it in a theater in the hood in Atlanta. The crowd clapped, they cheered, they yelled, ‘Get out, man! Yo—get out!’ It was all the stuff that we hoped the audience would say.”

Daniel Kaluuya wears a Gosha Rubchinskiy x Adidas Football sweatshirt and sweatpants; ’47 hat; Gucci socks; Kaluuya’s own sneakers.

“I booked The Florida Project when I was 6. I’m 7 now. It was really fun because during shooting I got to eat ice cream! I want to start my own YouTube channel, and the name of it will be I Am Crazy for Ice Cream because I am crazy for ice cream. I’m also so into fashion. I wear shorts in the movie, and they were so short. It was a struggle getting them on. Now, I’m like, ‘Mom! Where are my skirts? No more shorts!’”

Brooklynn Prince wears a Baby Dior dress; La Coqueta shoes.

Photographs by Juergen Teller; Styled by Edward Enninful

“I’m naked quite a lot in Beach Rats, and it’s a little strange to act when you’re naked. When the boom operator is standing over you, and you’re not wearing anything, it’s awkward. But, in the end, I didn’t find it difficult. I’m pretty comfortable with my body. Not in an ‘I’m happy to flaunt it for £5’ kind of way, but it does go deep into the psychology of someone trying to figure out their own sexuality, and their identity.”

Harris Dickinson wears a Calvin Klein 205W39NYC shirt, pants, and boots.

Photographs by Juergen Teller; Styled by Edward Enninful

“As an actor, people put you in categories. It’s ‘Oh, she has an accent,’ or ‘She doesn’t have an accent,’ or ‘She can do this accent,’ or ‘No, she can’t.’ They’ll say, ‘She’s a pretty blonde, so I don’t know if we can see her in a comedy.’ So I know that for Fatih Akin to pick me was a big risk because he’s very well known in Germany as a director who casts unknowns or people he discovers who are not actors at all. In the beginning, he got a lot of backlash for it. And, in truth, I don’t think I could have played this character five years ago. Now I’m ready to shed any beauty look. I want to be stripped of any pretense, of any glamour.”

Diane Kruger wears a Rosamosario romper; Christian Louboutin shoes.

Photographs by Juergen Teller; Styled by Edward Enninful

“When I was 14, I auditioned for an Off Broadway play. The scene was about a bris, the Jewish tradition of a child having the tip of his penis snipped off. 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 monologue, and, at the end, the director said, ‘Thank you very much, and it’s pronounced bris.’ I did not get the part.”

Ben Stiller wears a Gucci coat; Olatz pajamas.

Photograph by Juergen Teller; styled by Edward Enninful

“When I was 6, my favorite film was Robin Hood: Men in Tights. It’s got a lot of adult jokes, and it was really inappropriate for a child to see. In school, they asked us, ‘If you were to make a potion, what would you put in it?’ Even then, I could recall lines of movies, and I said, ‘The testicles of a newt!’ I got called up to the front of the class and was asked why I put testicles in my potion. I had no idea what testicles were—I just loved the film.”

Margot Robbie wears a Dolce & Gabbana top, shorts, and shoes.

Photographs by Juergen Teller; Styled by Edward Enninful

“I was late to the game on The Room, which is considered by many to be the worst movie of all time. For years, I would see this billboard in L.A. that Tommy Wiseau, the actor and star of the movie, had paid to have up on Highland Avenue. It was a picture of him, sort of glaring down at you, with the words THE ROOM and a phone number. I was like, ‘What is this? Do you call the number and this crazy, weird, vampirelike guy can be in your movie?’ But then I started reading The Disaster Artist, which was written by one of the other actors in the movie, and before I was halfway through, I just knew it was such an incredible, bizarre story, unlike any other in Hollywood, about outsider artists trying to achieve their dreams. I was instantly drawn to Tommy. It’s almost like we were made for each other.”

James Franco wears a Balenciaga shirt; his own pants.

Photographs by Juergen Teller; Styled by Edward Enninful

“To play Molly Bloom, I thought about what women have to become in order to find power in a society where men are making all of the rules. I was like, ‘Oh, my gosh—the Kardashians are an incredible example of women who have their own sense of entrepreneurial power.’ And in real life, Molly looked a lot like them. For research, I actually watched Kim’s tutorial on face shading and contouring. As the movie goes on, Molly transforms into this idea of what a woman has to be in order to be heard: The heels get higher, the necklines are lower, the hair is longer. It was quite a departure for me, physically. And the strange thing is, I don’t look like myself at all in this film, and so many people have said to me that I’ve never looked better.”

Jessica Chastain wears an Oscar de la Renta dress; Sophie Buhai earrings.

Photographs by Juergen Teller; Styled by Edward Enninful

“Until I read the script for Lady Bird, I had never encountered a female heroine who very much sees herself as a female heroine. In films, you rarely see young girls who love themselves. Lady Bird takes the self-confidence thing to a new level. She knows she’s going to be someone. And she has something to say, even if she doesn’t quite know what it is yet.”

Saoirse Ronan wears a Chanel dress.

Photographs by Juergen Teller; Styled by Edward Enninful

Did you have an audition outfit back when you were starting out? I had multiple outfits. Much like a costume box. I would change between auditions. I remember changing in the car on the freeway. I’m still a fast changer. And discreet. I have a talent for taking my clothes off quickly.

What was your first favorite film? The Sound of Music. It was very influential. And I got to meet Captain von Trapp while filming All the Money in the World [Christopher Plummer replaced Kevin Spacey after Spacey was pulled from the project]. We were about to be in this movie together, and I thought, How soon is too soon to ask Christopher Plummer to sing “Edelweiss” into my phone for my daughter?

Michelle Williams wears a Louis Vuitton dress.

Photographs by Juergen Teller; Styled by Edward Enninful

“I play real people a lot. And it is a huge responsibility. Anytime you are playing somebody who was alive, for good or for bad, that performance becomes a version of an official record of what happened: what motivated them, what obstacles they faced, and how they got through their particular struggle. There’s a degree of leeway that you can allow yourself as long as you’re not turning good guys into bad guys, or knowledge into ignorance. Having said that, it’s a little easier playing someone who’s no longer living. Because then you don’t have to meet them.”

Tom Hanks wears a Tom Ford suit, vest, and shoes; Boss shirt; Rolex watch.

Photographs by Juergen Teller; Styled by Edward Enninful

“I had a successful soap opera career in Mexico, but I left my fame and my comfort and I moved to Los Angeles because I wanted to make films. I was very, very famous in Mexico, and in the States I was working as an extra. People thought maybe I was running from the police. Why else would I leave everything I had to play a maid? I told them, ‘This industry is going to change. We are too strong of an economic force to be ignored forever.’”

Salma Hayek wears a Saint Laurent by Anthony Vaccarello dress; Cartier earrings.

Photographs by Juergen Teller; Styled by Edward Enninful

“I was loosely attached to Call Me by Your Name for four years. It never seemed like it was coming together, and then it did. Now I’ve spent nearly two years promoting it. So, in many ways, it will be the project of my youth. When I’m older, I’ll look at this film and remember what it was like to not be jaded, old, and washed up. I’ll look back and say, ‘Oh, when I was young…’”

Timothée Chalamet wears a Sandro jacket and pants; Schiesser tank top; Sermoneta Gloves gloves; Calvin Klein 205W39NYC boots.

“My first kiss was at a party, when I was 12 or 13, during my first term at a coed school, so, you know, hormones were raging. A girl named Dora had this party when her parents were out of town, and it was literally a bacchanalia for 13-year-olds. No one was having sex, but it was just like, ‘Oh, we all get to kiss each other.’ And there were around 200 people there. It was about five hours of everyone going, ‘Have we made out yet? No? Let’s go!’ To this day, my friends and I will be in a pub or at dinner and say, ‘Remember Dora’s party?’ and sigh. It was an awakening.”

Andrew Garfield wears a Shrimps coat; Michael Kors sweater; Sunspel sweatpants.

Photographs by Juergen Teller; Styled by Edward Enninful