Welcome to a new series on watch this: feel that called Spotlight.
In these posts, I’ll feature a collection of films and/or TV series that showcase the work of a particular actor, writer, or director. I’ll talk about why this person is so great, share some fun facts about them, and recommend what I think are the films and TV series in their filmography that you shouldn’t miss.
A little while ago, I polled @watchthisfeelthat Instagram followers to help me decide who to feature first. Phone screens were tapped and the choice was clear — so, the first spotlight will be on one of my favourite actors, Jake Gyllenhaal.
Part theatre nerd, part everyman, and part intense student of life, Jake Gyllenhaal is an actor whose body of work should not be missed. He has worked with unbelievably talented directors like the late Jean-Marc Vallée, Denis Villeneuve, David Fincher, and Ang Lee; is set to play the role of Iago across from Denzel Washington’s Othello on Broadway next spring; is currently starring in his first TV series, Presumed Innocent on AppleTV+; and has a role in The Bride, his sister Maggie’s next directorial feature based on The Bride of Frankenstein.
But wait — who is Jake Gyllenhaal, anyway? No one outside of his inner circle truly knows — and I like that. Even though I love to dive into the lives and work of actors, I enjoy when an actor like Jake can shapeshift and disappear into his characters, so I can immerse myself into the story without being distracted by the presence of a movie star. Pair this with his funny but surface-level interviews on Fallon, Kimmel, and the like, and you have an enigmatic film star who continues to surprise audiences with his choices.
This is not to say we don’t know some things about his personal life — he has dated a few A-list actresses in his past, and who can forget the brief relationship he had with a certain pop singer who immortalized his then-boyfriend behaviour in a song (followed by a 10-minute version of that song).
Nevertheless, Jake is an extremely versatile and intense actor who shows a deep commitment to his characters, and an enduring passion for storytelling. Now age 43, he has been acting for over 30 years and has extensive film credits that span multiple genres, including drama, romance, voice acting, action, biopics, psychological thrillers, and more. He even does theatre! (scroll down for a taste of his stage acting).
Read on for more about Jake, including what I deem to be the essential Jake movies that will leave you intrigued, entertained, and deeply affected.
THE ESSENTIAL JAKE
Just when I think I can categorize Jake as a serious, moody actor, he takes a left turn and does a Michael Bay movie, sings to children as a crazy music man in a comedy special, or plays an ex-MMA fighter turned bouncer in the remake of Road House. He’s like the handsome jock in high school who’s secretly smart and creative — he can do it all.
Lately more than ever, Jake seems to be following the “one for them, one for me” philosophy, oscillating between more commercial “popcorn” films where he can have fun and play to a broader audience and those he wants to do for personal or artistic reasons. In interviews, he has admitted to choosing roles largely due to which director he would get to work with, and I wouldn’t be surprised if he ends up directing someday himself.
Before we go any further, let’s start at the beginning — well, near the beginning of Jake’s career. 10 years after he debuted in 1991 as Danny Robbins, Billy Crystal’s character’s son in City Slickers, Jake made a name for himself as the titular character in the 2001 drama/sci-fi/mystery movie, Donnie Darko.
IMDB Summary:
After narrowly escaping a bizarre accident, a troubled teenager is plagued by visions of a man in a large rabbit suit who manipulates him to commit a series of crimes.
The film is mostly dark with comedic moments that share a similar energy to films like American Beauty and Heathers. I especially loved the little dinner table tiff he and his sister (played by his real-life sister Maggie) had — you have to believe there was some real emotion behind that scene. Also starring three icons of the 90s: Jena Malone, Drew Barrymore, and Patrick Swayze, this weird movie has become a cult classic, and it has a killer soundtrack.
![images of Jake Gyllenhaal acting in three movies: Zociac, Nightcrawler, and Brokeback Mountain.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd4b530f6-df88-4fc6-9ad1-7fe0e76c8ddf_748x1018.png)
![images of Jake Gyllenhaal acting in three movies: Zociac, Nightcrawler, and Brokeback Mountain.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd0df511-25ee-49a1-9f64-c83008ae3b1c_1494x761.png)
![images of Jake Gyllenhaal acting in three movies: Zociac, Nightcrawler, and Brokeback Mountain.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6de6b3b2-493e-4422-9e9f-3106696608e9_660x1009.png)
In 2005, Director Ang Lee gifted us with a nearly perfect casting choice of Jake as Jack Twist in the tragically romantic film, Brokeback Mountain. Amid breathtaking scenery and excellent, nuanced performances by Heath Ledger, Michelle Williams, and Anne Hathaway, Jake’s performance as Jack was heartfelt, genuine, and showed a maturity beyond his then-only 24 years. This film deserves a million newsletter posts written about it, so instead, I’ll leave it here by simply saying — watch it. Or if you’ve seen it already, watch it again.
After Brokeback Mountain established Jake’s star quality and acting talent, other esteemed directors came calling, including David Fincher. In 2007’s Zodiac, Jake portrayed Robert Graysmith, the real-life cartoonist turned investigator, codebreaker, and writer who penned the non-fiction book of the same name about the Zodiac Killer who was active in the 60s and 70s in California. I’m a fan of Fincher, as you may have guessed from my previous newsletter post that included The Game, so it didn’t surprise me that Fincher knocked it out of the park again with Zodiac, which featured excellent performances from not only Jake but also Mark Ruffalo and Robert Downey Jr. All three actors are so believable in their roles — but Jake especially shines as Graysmith, showing us a man who is pure and naive, but also driven by a quiet strength and a doggedness to discover the truth. Highly recommend.
In 2009’s Brothers, Jake showed us more of his ability to emote on screen, when he played the supporting role of Tommy Cahill, brother to Tobey Maguire’s Captain Sam Cahill. Mostly in scenes with Natalie Portman, Jake gives a sweet and subtle performance in contrast to Maguire’s dramatic, emotional portrayal of PTSD in this family melodrama.
![Photos of Jake Gyllenhaal in movies Love and Other Drugs, Donnie Darko, and Prisoners.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8a4b6ddb-b35d-4b33-8715-ef408b684c04_886x971.png)
![Photos of Jake Gyllenhaal in movies Love and Other Drugs, Donnie Darko, and Prisoners.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd1317f73-fc70-4671-8c06-b8a81c673bce_1478x854.png)
![Photos of Jake Gyllenhaal in movies Love and Other Drugs, Donnie Darko, and Prisoners.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdbed9dfb-ca1f-4de7-8917-24f8c5837f8a_1374x1030.png)
Jake needs to make more rom-coms! Although he has honed the craft of playing dark, complicated characters, he’s also great at playing the handsome, charming everyman. In this case, the handsome everyman is a pharmaceutical sales rep named Jamie Randall who meets a woman who changes his life. In Love and Other Drugs (2010), Jake reunites with Brokeback Mountain castmate Anne Hathaway and their chemistry is palpable. Love and Other Drugs is a funny, romantic film that aside from some cringy comedic moments and bad jokes, is a pretty perfect romantic comedy.
Prisoners was my first introduction to Canadian Director Denis Villeneuve. Now well-known for films like Dune, Dune 2, Arrival, and Sicario, by 2013 when this movie was made, Villeneuve had earned critical acclaim for his work but was only just breaking into Hollywood. This is a film that will keep you guessing until the end, and it features a staggeringly good, gut-wrenching performance by Hugh Jackman as a desperate father searching for his missing daughter. Jake plays the detective working the case, and to his character Detective Loki, he brings a set of very interesting physical choices and acting nuances. You must watch this film, and be sure to stay with it until the end.
In my opinion, one of Jake’s best performances to date was in 2014’s Nightcrawler. Here, in this psychological crime thriller, Jake is at his best — deeply committed to the character, dark, weird, and intense. For the film, Jake ran 15 miles each day to the set, lost 30 pounds, and took inspiration from coyotes to portray Louis Bloom’s starving, ruthless, feral-like energy. The film is more than a thriller, with a clever script and a subtext that makes commentary about capitalism and the media. Steel your stomach and give this a watch — you’ll see what Jake is capable of as an actor, which is, in a word, impressive.
JAKE’S HIDDEN GEMS:
Having grown up in Hollywood and been acting since he was young, Jake’s filmography is extensive, so I won’t be covering all of it here — I haven’t even seen all of his films — and I’m a fan!
What I will highlight here are a few films that are in my opinion, Jake’s hidden gems. In these films that may or may not be on your radar, you’ll enjoy more amazing performances from Jake:
Nocturnal Animals (Crave, Amazon Prime) - Turns out Tom Ford isn’t just a great fashion designer, he’s also a very interesting writer/director. This neo-noir film is visually and emotionally dramatic, and in it, Jake expertly plays two roles at once, sharing scenes with talented actors Amy Adams and Michael Shannon.
The Guilty (Netflix) - A real actor’s piece, this film relies heavily on one of the actor’s most important tools — the voice. Jake plays a demoted detective who is working in a 911 call centre and has to do what he can to save a distressed caller.
Everest (rent on Amazon Prime or Apple) - A stunning and emotional biographical adventure film with an excellent ensemble cast, Everest is an underrated movie that introduced me to the very talented actor Jason Clarke. Even in this supporting role, Jake makes an impact as he portrays real-life American mountaineer and mountain guide, Scott Fisher.
Enemy (Amazon Prime, Crave) - You may ask yourself, what was this movie about? And you may hate it. Regardless, what you will see in this surrealist psychological Denis Villeneuve thriller are Jake’s stunning acting chops yet again — this time, playing two characters at once. Canadian actor Sarah Gadon (also featured previously on watch this: feel that) also stars, and Torontonians will likely recognize some filming locations.
THEATRE JAKE:
As teased above, Jake also does theatre — and although I’ve never seen him live, based on this clip below — man, is he good! Also: how amazing would it be to see him in Othello with Denzel next Spring? A girl can dream.
In 2002, Jake made his theatrical debut in London, playing in Kenneth Lonergan’s This is Our Youth, joining a list of actors who have also played the role of Warren which includes Mark Ruffalo, Casey Affleck, Kieran Culkin, and Michael Cera.
In 2017, Jake sang his heart out as Georges Seurat in Sondheim’s Sunday in the Park with George, for which he was praised widely for his vocal ability.
Here’s an excerpt from his role in Nick Payne’s play, A Life, for which he was nominated for a Tony Award in 2019:
MORE JAKE:
A quick list of more of Jake’s film credits that are worth checking out:
Demolition
End of Watch
October Sky
Jarhead
The Good Girl
Stronger
Source Code
Life
Southpaw
![Pictures of Jake Gyllenhaal eating food or posing with food.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fee908132-4a91-4d11-8367-85d46ce1c443_1007x1152.png)
![Pictures of Jake Gyllenhaal eating food or posing with food.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fff5218c1-434c-4e84-87e4-d532fe8ebdc5_846x1073.png)
![Pictures of Jake Gyllenhaal eating food or posing with food.](https://substackcdn.com/image/fetch/w_474,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F82e7918e-4779-414e-9741-4a977eadc75a_1099x1290.png)
FUN FACTS:
Jake co-wrote a children’s book called The Secret Society of Aunts and Uncles.
He loves to run, cook, eat, and chew on his headphones — all activities that were widely reported and hilariously documented in the now dormant Twitter/X feed, @jakeactivities.
His godmother is Jamie Lee Curtis.
His mother Naomi Foner wrote the script for Sidney Lumet’s film, Running on Empty, which starred River Phoenix.
Jake is funny: he has hosted Saturday Night Live three times, had guest spots on Inside Amy Schumer and John Mulaney and the Sack Lunch Bunch, and has some pretty hilarious press junket interviews in the YouTube archives.
STILL ON MY WATCHLIST:
Films and TV series even I haven’t seen yet but am looking forward to:
Presumed Innocent
The Sisters Brothers
Wildlife
Okja
What’s your favourite Jake Gyllenhaal movie? Tell me in the comments, and follow me at @watchthisfeelthat on Instagram for my next poll to decide who the spotlight will shine on next in this series — or if you’re not on Instagram, send me a message and tell me who you’d like to see featured:
Update - I watched Presumed Innocent (Season 1). Jake was good but his real life brother in law Peter Sarsgaard stole the show with his performance as Tommy Molto.