ESQ&A: Jake Gyllenhaal
Esquire Singapore|August 2019

The Cartier Santos-Dumont ambassador talks failure, action heroes, theatre and what it means to be a man.

Norman Tan
ESQ&A: Jake Gyllenhaal

ESQ: The Cartier Santos timepiece is named after Brazilian aviator Alberto Santos-Dumont, who famously said: “Even in the worst of times, you must never give in to discouragement, but instead use your failure to start again.” How do you relate to this quote as an actor?

JAKE GYLLENHAAL: There is this wonderful quote that basically says: “We learn from our failures more than we learn from our achievements or triumphs. And, if that’s so, why don’t we learn about the people who failed?” I sort of love that idea on why don’t we hold up to people who came in second place. I believe that deeply. Failures are some of the most beautiful times to look back on because they inform the changes and decisions you make to move forward. That sense of birth comes right out of that time. So I think you have to be hopeful, have a vision, see where you want to go and believe in it. Trust your instinct. You can’t constantly be trying to look for failure. That’s not a good thing. But when you don’t succeed, that’s when the lesson comes.

ESQ: You have a knack for playing extreme characters, but presenting them in an honest way. Why are you drawn to characters like Lou Bloom in Nightcrawler, Morf Vandewalt in Velvet Buzzsaw and Mysterio in Spider-Man: Far From Home?

JAKE GYLLENHAAL: I have a desire to understand why people are the way they are. So often, my own judgement of someone in the past has led me away from discovery. More and more, I discover that if I begin with judgement, I become curious about it. And every time I move into that idea, it makes me realise something about myself.

This story is from the August 2019 edition of Esquire Singapore.

Start your 7-day Magzter GOLD free trial to access thousands of curated premium stories, and 8,500+ magazines and newspapers.

This story is from the August 2019 edition of Esquire Singapore.

Start your 7-day Magzter GOLD free trial to access thousands of curated premium stories, and 8,500+ magazines and newspapers.

MORE STORIES FROM ESQUIRE SINGAPOREView All
THE MILD HANGOVER
Esquire Singapore

THE MILD HANGOVER

Hangovers get a bad rap. We know. If you’ve gotten this far in the magazine, you’ve surely divined that we’re mildly hungover most of the time.

time-read
2 mins  |
November 2022
AN ELECTRIC FUTURE
Esquire Singapore

AN ELECTRIC FUTURE

Polestar, the minimalist electric Swedish car brand, turns the voltage up on its competition.

time-read
3 mins  |
November 2022
LET'S GET REAL (ESTATE): LUXURIOUS LONDON
Esquire Singapore

LET'S GET REAL (ESTATE): LUXURIOUS LONDON

Royalty, shopping, the best tea and scones the world has to offer, and a lifestyle worthy of what you're working for. Here's why London is ripe for your next investment

time-read
4 mins  |
November 2022
NEXT UP....ZARAN VACHHA
Esquire Singapore

NEXT UP....ZARAN VACHHA

As Co-founder of the events and talent agency Collective Minds and Managing Director of the Mandala Masters, Zaran Vachha is definitely not new to the culture scene, but he's certainly shaping what comes next.

time-read
6 mins  |
November 2022
WHAT I'VE LEARNED...
Esquire Singapore

WHAT I'VE LEARNED...

I DON’T WEAR SOCKS except in January.

time-read
3 mins  |
November 2022
The Body Is a Language
Esquire Singapore

The Body Is a Language

A bad handshake is such a turnoff; we feel irked when someone rolls their eyes at us; we can't stop pacing when we're nervous-ever wondered how certain body language has the power to change how we feel instantly? We explore why.

time-read
4 mins  |
November 2022
EYE OF THE TIGER
Esquire Singapore

EYE OF THE TIGER

Hailing from Singapore, Japan and Brazil respectively, Evolve Mixed Martial Arts (MMA) athletes Darren Goh, Hiroki Akimoto and Alex Silva are proof that the ring demands as much from mind as it does from matter.

time-read
10+ mins  |
November 2022
THE ADONIS COMPLEX
Esquire Singapore

THE ADONIS COMPLEX

With the rise of superhero culture making a return and bringing with it the celebration of the classically ‘masculine’ body type, can men really overcome the pressure to conform when culture keeps getting in the way?

time-read
8 mins  |
November 2022
FUNNY BUT TRUE
Esquire Singapore

FUNNY BUT TRUE

A comedian, an iconic Singaporean, and now a man much evolved. After overcoming two years of pandemic limbo, unlocking career milestones one after another and undergoing a life-defining physical transformation, Rishi Budhrani is ready to emerge into the world renewed-and anew.

time-read
10+ mins  |
November 2022
LIKE NO OTHER
Esquire Singapore

LIKE NO OTHER

With its horological triumphs, Hermès has truly come into its own as a watchmaking maison. In this exclusive interview with Esquire Singapore, CEO of Hermès Horloger, Laurent Dordet sheds some light on his timepieces' rising stardom and the importance of being different.

time-read
4 mins  |
November 2022