Jake Gyllenhaal turns 40: Here’s his best looks, performances, screen partners, nude scenes (!!!) and more

I don’t know if you guys know this — perhaps you don’t have this written in your calendars four times like I do, in which case I just feel sorry for you — but today marked a very important week for us terminal case Gyllenhaalics. Today, Saturday, December 19th, is Jake Gyllenhaal’s 40th birthday! Huzzah indeed! For those of us who’ve been following his career real close (over 1100 posts close, haha) for the past nineteen years, since Donnie Darko hit in 2001 basically, this feels momentous. That sweet little nutter’s become a grown ass man!

Note: text is largely as originally written on My New Plaid Pants, including the daily timeline.

Anyway I felt like I had to mark the occasion properly, so I’m going to do a Top 5 Jake list every single day this week. It only seems right after all he’s given us. Starting us off today’s topic will dive into one of Jake’s favorite sports — mental illness! I think you could classify a full 50% of Jake’s roles as at the very least obsessive, whether he’s losing years of his life trying to solve a serial killer’s cryptic riddles, or dancing on stage with an adorable super-pig. Forthwith my faves!

My 5 Favorite “Jake’s Nuts!” Performances

Mr. Music, John Mulaney & the Sack Lunch Bunch

Louis Bloom, Nightcrawler

Morf, Velvet Buzzsaw

Adam / Anthony, Enemy

Johnny Wilcox, Okja

Runners-up: I am classifying Donnie Darko, Bubble Boy, andZodiac as runners-up only on the technicality that they aren’t actually as messed up as these other five — Donnie & Robert Graysmith are both basically right on about their respective obsessions, while Jimmy from Bubble Boy is just too dang harmless. 

Happy Day 2 of Jake Week, where we’re celebrating Jake Gyllenhaal‘s 40th birthday this upcoming Saturday with a different Top 5 list every single day. Yesterday I shared with you a list of my favorite crazy-pants performances from Mr. G that had him flailing his psycho-stick around for our enjoyment — well today I am going a little simpler on the one hand, in that this is an ode to the outfits his personhood has slipped into and made iconic, and a little less simpler on the other because I couldn’t pick just five. I had to double it. There are too many to choose from! (Sidenote: I tried to talk about actual memorable clothes here — the time will come for a list of Jake being naked, don’t worry.)

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My 10 Favorite Jake Gyllenhaal Costumes

His “Elliot from E.T.” costume in Donnie Darko

The Santa hat & thong combo from Jarhead

His blue-shirted Brokeback ensemble

His white boxing shorts in Southpaw

His blue polo in Lovely & Amazing

The Mysterio Cape! (Spider-twink included)

The tight-buttoned dress shirts in Prisoners

The buffalo-plaid in Nocturnal Animals (Aaron Johnson included)

The business-to-casual red suspenders in Demolition

That open cream shawl he wore to showcase his Persia bosoms

Runners-up: Jake in uniform in End of Watch, the Bubble in Bubble Boy, the art snobbery in Velvet Buzzsaw, the jean shorts in Okja

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Well today is Wednesday, the middle of the week, also occasionally known by some as Hump Day. And so it only seems right that today I list something I hinted at during yesterday’s post about clothing, which is… the exact opposite of clothing. This should lift everybody’s “spirits.”

My 5 Favorite Jake Gyllenhaal Nude Scenes

Group shower, Jarhead

Googling whilst gay, Velvet Buzzsaw

Forgot the camera in Love & Other Drugs

Sad suds in Southpaw

Washing by the river, Brokeback Mountain

Runners-up: Listen I could have listed half of Love and Other Drugs, as Edward Zwick was proper decent to us in that respect (if only the movie had been better). Bless that film.

And I did a compilation post once about Jake’s many many many “naked in the bathroom” scenes — see here — so there are several more exciting choices as far as those are concerned. I mean he literally seems to spend half of the movie Demolition in the bathroom — see here.

And he spends a lot of time showing off his manscaping in Enemy. And then, for historical sake, there’s this shot in Jarhead, which beat Brokeback to the punch giving us our first glimpse of Jake’s butt:

A true milestone, if you ask me! There are also the coulda-been scenes that we have been entirely denied — I can’t even post the caps of Jake papped naked-on-the-set of Everest because the studio freaked out about them and will send letters if one posts them, but if you google that shit it’s out there. In the end the scene got inexplicably, hatefully cut from the final film, which went on to deservedly flop for that alone. Fuck you, Everest!

And then there is the most upsetting absence of all — Jake chickening out and turning down Michael Pitt’s role in Bernardo Bertolucci’s 2003 hornt-up The Dreamers, opposite Louis Garrel & Eva Green. Can you imagine? I still weep myself to sleep at night over that loss…

Anyway I could go on and on and on. And on. And on! This is probably the lone topic in all of the world which I am the foremost expert on. My Film Studies degree put to excellent use! Ain’t ya proud, Mom???

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Well today we’re talking chemistry. Or better yet, as the noted physicist Dr. Paula Abdul coined it, Vibeology. What is Vibeology? Why, it’s the study of the chemistry between you and me. Or in this case, it’s the study of the chemistry between Jake Gyllenhaal and his co-stars. No man is an island, even one so oft brooding as Jake, and Jake has sparked off more than most. So today I’m going to give you his greatest screen partnerships, according to me. (At least until Jake and me make our movie together, in which case I will become numbers one through five, natch.)

My 5 Favorite Jake Screen Partners

Tom Holland, Spider-Man: Far From Home

Tatiana Maslany, Stronger

Riz Ahmed, Nightcrawler & The Sisters Brothers

Carey Mulligan, Wildlife

Heath Ledger, Brokeback Mountain

Runners-up: Jennifer Aniston, The Good Girl; Jena Malone, Donnie Darko; Anne Hathaway, Brokeback & Love and Other Drugs; Rene Russo, Nightcrawler & Velvet Buzzsaw; Michelle Monaghan, Source Code; Sarah Gadon, Enemy; Catherine Keener, Lovely & Amazing

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If you haven’t been here all week… what, you have something better to do? You know we are in the middle of a pandemic, right? We’re in the middle of a pandemic, it’s literally life or death out there, and you still can’t come to MNPP before Friday? I mean, I am trying to not be offended here. Trying, but failing. It’s fine. It’s fine. Whatever. I’ll carry on. So like I was saying, if you haven’t been here all week to see it, because you’ve been, I don’t know, preferring to stare at the wall then read all my hard work or whatever, then you’ve missed that I’ve spent all week celebrating the 40th birthday of the actor Jake Gyllenhaal, which is today!

I’ve been celebrating with lists! Ridiculous lists! Monday I did his best nutbag roles, Tuesday I did his greatest costumes, Wednesday I went lascivious and stared at his bum a bunch, and yesterday I picked his best screen partners. For today, our final day, I figured I’d better go big or go home. I mean I’d love to go home. Did I mention the pandemic? We should all be home. But I digress. Here on our last day of list-making I challenged myself to a most painful proposition. I have decided to not just pick my ten favorite Jake movies… BUT TO RANK THEM. Oh my god this one hurt, you guys. I am bloody, my brains are battered, and all for your entertainment. Enjoy!

My 10 Favorite Jake Gyllenhaal Movies… Ranked!!!

10. Jarhead (dir. Sam Mendes)

9. Okja (dir. Bong Joon-ho)

8. Source Code (dir. Duncan Jones)

7. The Sisters Brothers (dir. Jacques Audiard)

6. Zodiac (dir. David Fincher)

5. Wildlife (dir. Paul Dano)

4. Donnie Darko (dir. Richard Kelly)

3. Nightcrawler (dir. Dan Gilroy)

2. Enemy (dir. Denis Villenueve)

1. Brokeback Mountain (dir. Ang Lee)

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That number one was obvious from outer space, I’m sure. Now tell me yours in the comments…

I also included some bonus content in the Twitter thread I kept up all week for this series, so make sure you click over and check that out. There are very important pieces of the puzzle to be seen therein. Very important! 

Anyway I live in abject terror every day of my life that my fanboying over Jake will ever be seen by his own big beautiful eyeballs so god forbid he read this message himself, but we here at MNPP and AW truly do wish him the best 40th birthday. He’s been my favorite actor for 19 years and counting, and I don’t foresee that changing any time soon. He continues to challenge himself and do strong, interesting work, and the projects he’s got lined up on IMDb (all of which we’ve covered in minute detail already, of course) all sound like shit I wanna watch. Good work, and Happy Birthday, You.

And now a bonus! Because I am incapable of ever stopping. And also y’all deserve a treat after all this rambling. I noticed when I worked on the nudity list on Wednesday that Jake has a nude scene I’ve somehow never posted here on the site, which… well, that is a truly, wildly inexplicable thing. It’s from Velvet Buzzsaw, he does the cutest little “hey here’s my butt” waddle, and I’ve got the whole thing giffed right on after the jump…