Jake Gyllenhaal Talks Freezing Up on Spider-Man, Love Scenes With Jennifer Aniston, and Starting a Family of His Own

Jake Gyllenhaal has embodied a diverse range of characters throughout his storied Hollywood career, from cursed art critic and sexually conflicted cowboy to boxing champion and time-traveling prince. But during his Stern Show return on Monday morning, the 40-year-old actor seemed ready if not eager to embrace an altogether different kind of role—that of a husband and father.

He and French model Jeanne Cadieu have reportedly been dating since 2018, but the two took a major step last week when she appeared by his side on a red carpet for the very first time. They attended the New York Film Festival in support of Jake’s sister, actress and filmmaker Maggie Gyllenhaal, and her new movie “The Lost Daughter.” Howard suspected their red carpet debut was an omen of good things to come, quite possibly marriage.

Jake didn’t rule it out.

“I love her so much and she’s just such a good person,” he told Howard, explaining how well Jeanne fits in with Maggie and the rest of his kin. “My sister grabbed her and pulled her on that red carpet … and I was like ‘Oh yeah, it’s family.'”

Acting is time consuming work, of course, so Howard wondered if Jake feared his busy schedule might make it hard for him to settle down. “Do you think you could be a successful husband and father?” he asked.

“That’s all I want is to be a good husband and a father,” Jake responded. “That really is what I want and now that I have fulfilled a lot of things in my career that I feel comfortable with I can safely say that. I don’t know if I could’ve said that before.”

If anything, Jake felt having a family could make him an even better actor. As he sees it, that’s exactly what happened with his sister Maggie, who married actor Peter Sarsgaard in 2009 and now has two daughters. “Her life, her family, and her marriage has just deepened her work,” he explained, adding, “I think there comes a point where you either start getting more shallow or you start getting more deep in your work, and I think you have to incorporate those things into your life in order for that to happen.”

The Greatest Gift an Actor Ever Gave Him

Jake never went to acting school but looking back on the early days of his career there was plenty of on-the-job training. He told Howard his big break came as a senior in high school. He was all set to play Tevye in his class’s production of “Fiddler on the Roof” when he was called up to the big leagues to star opposite Chris Cooper in “October Sky.”

“It was one of the biggest regrets of my career, I gotta say. Tevye is the role,” Jake laughed before he and Howard sang a few lines from the “Fiddler” song “Do You Love Me?”

While Jake enjoyed making “October Sky,” he admitted being on a shoot for long stretches at a time wasn’t as thrilling as he’d always imagined. It was difficult work and Jake still had a lot to learn. Cooper played his father in the coming-of-age drama. As Jake explained it, the two shared several tense scenes and the eventual Oscar-winning “American Beauty” star taught him a few valuable lessons.

“[Actors] love screaming and yelling, you know? … I was doing it. I thought, take after take, I’m killing this. I’m just screaming and yelling,” Jake said. “Chris is a very quiet, composed man, very measured, very thoughtful … he comes up to me and goes, ‘I don’t know what you’re doing. You’re just yelling at me. Just listen to what I’m saying to you.’”

Jake said he was devastated, but thankfully that was an emotion his character needed to access within the scene. “My heart just went, ‘Oh god, I feel so embarrassed. Oh geez, what am I doing?’ And then … I just listened,” he recalled. “Then, as we talked, it really started to piss me off. What he was saying started pissing me off. And then … I was riding a real wave.”

“That was the biggest gift an actor’s ever given me, honestly,” Jake added.

How ‘Brokeback Mountain’ Went From Ahead of Its Time to Behind the Curve

Cooper’s advice was apparently well received because it wasn’t long before Gyllenhaal was winning accolades of his own. In 2005, Jake earned an Oscar nomination for starring opposite Heath Ledger in Ang Lee’s critically adored romantic drama “Brokeback Mountain.”

“Do you actually become good friends after a movie like that?” Howard asked.

“Yeah,” Jake responded. “With Heath we were friends before that and through it. It like fortified all of us, somehow, in a way. That was just a crazy experience. That was just unlikely for all of us.”

Jake played closeted gay cowboy Jack Twist in “Brokeback Mountain,” which was praised not only for its quality but also for the barriers it attempted to break down in Hollywood. Over 15 years later, Howard wondered if the world would be as receptive.

“Do you think that movie now could be made with two straight actors or would it be under fire?” he asked.

“I think about that. I do. I think probably the answer is no, but then when I look at it now as a way in which it paved an opportunity in a time when there was no real chance that, you know, two straight actors are going to play roles like that,” Jake responded, adding, “The amount of flak we got for that, it was crazy. For a year after that, the amount of conversations about what my sexuality was, I was like … ‘Everybody, just chill out.’”

Howard wondered if anyone in his camp had advised him against taking the role.

“Early on, there were people going, ‘What are you doing?’ I was like, ‘What am I doing? This is the most beautiful story I’ve ever read. With Ang Lee? … He’s one of the best filmmakers,’” Jake said. “They were stupid, frankly.”

Pillow Talk With Jennifer Aniston

Heath wasn’t the only on-screen love interest Jake spoke about on Monday. He also opened up about starring in the 2002 film “The Good Girl” alongside Jennifer Aniston, whom he had a crush on from watching “Friends.”

“It was torture … but it was also not torture. I mean, come on. It was like a mix of both,” he said of the steamy on-camera moments they shared.

As erotic as they may look to moviegoers, Jake said love scenes are generally anything but while on set. “There are maybe 30, 50 people watching it … that doesn’t turn me on,” he said. “Most of the time, it’s oddly mechanical. Also, it’s a dance … you’re choreographing for a camera.”

For his “dance” with Aniston, Jake revealed something called “the pillow technique” was used for a little added separation and discretion. “That was just preemptive and used generally always when actually in a horizontal place in that movie,” he recalled. “I think that was actually a Jennifer suggestion. She was like, ‘I’m putting a pillow here.’ That was it, that was all she said.”

Freezing Up on ‘Spider-Man’

Jake has scores of blockbusters under his belt now and has received dozens of acting accolades, but even he isn’t immune to the pressures of appearing in the multi-billion-dollar Marvel Cinematic Universe. He told Howard he struggled while shooting his first scenes of 2017’s “Spider-Man: Homecoming.”

“That acting is hard,” Jake said, explaining he’s usually involved with projects from the very beginning but in this instance joined the superhero franchise after it was well established. “It was like, you gotta deliver in that space. And it was a whole different craft.”

Luckily, his co-stars Tom Holland and Samuel L. Jackson helped guide him through the process. “The first day of shooting … I went up to Tom Holland and I was like, ‘Dude, help me out.’ He was like, ‘It’s all good, man,’” Jake recalled. “I think I just put a lot of pressure on [myself because] I love Spider-Man, I love this world, I wanna kill it here.”

Jake’s portrayal of the villain Mysterio involved a suit of armor, a cape, and even a beard. While facial hair may be left to the actor’s discretion on some projects, Howard wondered if on one of Marvel’s juggernauts those kinds of decisions were made by studio bigwigs.

“Beard length was definitely an issue,” Jake admitted. “The beard was already something they desired … There’s that first day before you start and everyone’s like, “Longer? Shorter?’ … They’re like, ‘Alright, beard’s not as nice as Chris Evans’s, but, you know, it’ll do.’”

Losing a Tony to a Familiar Face

Though he is primarily known as a film star, Gyllenhaal is at least equally as passionate about his theater work which goes back nearly 20 years. “My agent knows how joyful I am when I’m on a stage,” he explained to Howard. “I need it as food … the animal that I am, I need the stage. Like, I need it as a playing ground, as a way of saying like, ‘You’re still alive, you can get up in front of these people and you still have that energetic exchange.’”

For his role in “Sea Wall/A Life,” the actor received his first Tony nomination though he ultimately lost to former scene partner Andrew Burnap. “I want to win, I put a lot of hard work into that thing,” he admitted before revealing he felt nothing but joy for Burnap, who he ran lines with when the latter was fresh out of Yale. “It was amazing. I mean, when he went up I threw my arms around him. I was so excited for him.”

“Everyone has their time,” Jake concluded. “I’m so pissed about so many other things, there’s no reason to be pissed about that.”

Hello Operator

Jake is both the star and a producer of his latest film, “The Guilty,” an Antoine Fuqua-directed thriller about an embattled 911 operator having a very difficult day. The movie was made during the second wave of COVID, so he and Fuqua did their best to keep the shoot short—they wrapped in just 11 days—and the cast small.

“This movie, when you see it, it’s all Jake,” Howard said.

“Sorry about that, by the way,” his guest laughed.

In all seriousness, Jake hoped his film might help audiences better understand what emergency operators go through on a daily basis. “[We are] shouting out to the 911 dispatchers across the country and across the world. That job is incredible,” he said. “You’re dealing with people on the worst day of their lives and you don’t get to know what happens [after you hang up]. Often times they’re the unsung heroes in that space.”

“Also, the movie is about mental health. Yeah, the person on the other end of the line … but also the mental health of the person who is answering that call,” Gyllenhaal continued. “That’s why Antoine and I wanted to make that movie … This is a movie about all of us and how broken our systems are and how much we project on other people and the mistakes we make as a result of that.”

“The Guilty” starring Jake Gyllenhaal is now streaming on Netflix.