Oscar History

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William Holden in Picnic

"I find Holden has a more earthy sex appeal in his early roles, you could kick your shoes off and put them on his lap and he wouldn't flinch." - Mark

"My mother's favorite actor. His dance with Kim Novak is an unforgettable movie moment." -Jaragon

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Posterized: Jake Gyllenhaal

Jake on the set of Everest (2015)With Enemy, Dennis Villeneuve's trippy new thriller starring Jake Gyllenhaal and Jake Gyllenhaal opening this weekend,  it's time to look back on this actor we've loved ever since he stared in a mirror and saw a demonic rabbit staring back at him. Jake's been picky in his career making less features than other stars who've been in the business for nearly a quarter century. (Since his parents are both in the industry, he started young.) Jake recently turned 33 --  the Jesus year (!) which we'll pretend explains the hair --  and he's already built an enviable filmography having starred in at least one bonafide classic (Brokeback Mountain) and two others that might also stand the test of time (Donnie Darko, Zodiac).

So the question is now, what kind of a second act is his career going to have now that he's in Hollywood's preferred age range for male movie stars (thirtysomething through the fortysomethings is when most of the iconic roles happen)? His last three pictures have all been very good and very different (End of Watch, Prisoners, Enemy) which is probably a good sign. 

Enemy is his 24th feature. How many have you seen? Let's take a trip back in time...

Child Actor (1991-1993)
City Slickers, A Dangerous Woman, Josh and S.A.M.

 Adolescence (1998-2001)
 Homegrown, October Sky, Donnie Darko

Dreamy Troubled Boyfriend Phase (2001-2002)
Bubble Boy, Lovely & Amazing, The Good Girl 

Flailing Around (2002-2004)
Highway, Moonlight Mile, The Day After Tomorrow 

Ascendance - "Gyllenhaalics" becomes a thing (2005)
Proof, Jarhead, Brokeback Mountain

Headliner in All Star Ensembles (2007-2009)
Zodiac, Rendition, Brothers 

Leading Man / Mixed Results (2010-2011) 
Prince of Persia, Love and Other Drugs, Source Code 

Right Now (2012-2014)
End of Watch, Prisoners, Enemy

How many have you seen? How many did you love? And what do you think Jake's future will hold? He's currently filming the mountain climbing drama Everest (for which he has returned to body-ody-ody) and has already wrapped Nightcrawler (2015), another thriller (which seems to be his genre of choice) for which he became skeletal a la McConaughey & Leto this past year.


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Reader Comments (37)

I've seen 8 and liked them all. loved Zodiac and End of Watch. I'm not worried about his future career. he's fine.

March 14, 2014 | Unregistered Commenterbrace


March 14, 2014 | Unregistered Commenterwill h

I **REALLY** want to see Nailed. I completely understand why David O. Russell has suppressed it because who wants to show the film that nearly destroyed your career and harmed your mental health? It is to the point it has completely changed how he directs films for a lot of people with this film marking the turn in the road. I am curious.

March 14, 2014 | Unregistered CommenterCMG

16, which is a surprise.

I think he's a terrific actor, able to go big and small, a talent I'm not sure he always had. For me it was 'Brothers' where I first thought he displayed his talents best, kind of a haunted every-man, which he's shown again in 'Enemy' and 'Prisoners' to equal levels.

March 14, 2014 | Unregistered CommenterBrianZ

I like the Highway and Moonlight Mile posters side by side. And the Brothers poster is surprisingly, um, sexual.

I've seen 8. Unsurprisingly, Brokeback and Zodiac are my favorites, as I'm sure they are for many. And it's been a while, but I'm still pretty fond of The Good Girl.

Jarhead, naturally, is the gift that keeps on giving for Gyllenhaalics

March 14, 2014 | Unregistered CommenterMike in Canada

I've seen 15, which surprised me. He had a really nice run from Proof to Brothers. I was really into what he was doing at the time. Didn't see End Of Watch, heard mixed things about it, but loved Prisoners, so I'm kinda excited to see where he goes next.

March 14, 2014 | Unregistered CommenterV

I love Jake but realised I've only seen 10. My favs are Brokeback and Donnie Darko. I just watched Prisoners the other day and thought he was brilliant ( as was Hugh). Thanks for this list. Might have to have a JG marathon.

March 14, 2014 | Unregistered CommenterJoanne

I've seen 14, I must be a Gyllenhaalic.

March 14, 2014 | Unregistered Commentermurtada

Seen an loved 8 of the last 9, 13 overall. I'm a fan of his "mixed results period." It was either Source Code or Love and Other Drugs that put me on the Gyllenhaalic train.

March 14, 2014 | Unregistered CommenterQueermyntcritic

13. As terrible as the movie is, I still say the poster for LOVE AND OTHER DRUGS is incredible. Actually makes it look romantic *and* comedic (and sexy).

March 14, 2014 | Unregistered CommenterGlenn

Surprisingly I've only seen 6 and I thought I was a pretty big fan (at least for a while). Loved Brokeback and Darko and really liked Jarhead and The GoodGirl. End of Watch has been sitting on my Netflix queue forever so I need to get around to that, and Enemy looks verrrry interesting although I hate it's pallid, jaundiced color palette.

I think he makes really interesting choices even if they don't all work. I know he's said in a few interviews that he chose movies based on what their message was, which is interesting and even noble but maybe not enough. I mean, c'mon, Jake, maybe also take the script, director, etc. into consideration as well? Although maybe he didn't mean the message was exclusively the only thing he considered (hopefully).

March 14, 2014 | Unregistered CommenterDJDeeJay


1. Brokeback Mountain
2. Donnie Darko
3. Zodiac
4. End of Watch
5. The Good Girl

Liked a Lot

6. Brothers
7. Jarhead
8. Source Code
9. Prisoners
10. Lovely & Amazing
11. The Moonlight Mile (yes I'm serious, but probably should revisit)


12. Love & Other Drugs
13. October Sky


14. City Slickers (but come on, it was barely a role)
15. The Day After Tomorrow

Can't wait for Enemy. Plus, this was a nice reminder that he has an incredible batting average, as far as I'm concerned.

March 14, 2014 | Unregistered Commentereurocheese

I suppose it should be obvious, but obviously I have seen every single one of these.

And what CMG said - I would KILL to see Nailed, and think part of what I'm holding against David O. Russell these days is the fact that I have not seen Nailed.

The posters for Enemy have been so great, I've loved them all.

March 14, 2014 | Unregistered CommenterJA

I've seen 15, which was strangely both higher and lower than I thought it'd be. I guess that means I really like and can be somewhat indifferent towards Gyllenhaal all at once.

CMG and JA, I'm also DYING to see Nailed. Mainly for selfish reasons, considering I was an extra in the scene where Jessica Biel's character gets shot with the nail gun (that never got finished). I mean, literally my entire face filled the camera at one point because of the opening tracking shot (I played a waiter in the restaurant). Gah! But it really is unfortunate about the release because based on what I heard/saw, it seemed like a good time. I'd definitely love to see a finished product.

Unfortunately, Jake wasn't on set that day so I couldn't gawk, BUT James Marsden was within reach and that was definitely okay with me. Two thumbs up for that guy.

March 14, 2014 | Unregistered CommenterKeelay!

I've seen 12- did not realize until now that Mr Gylenhaall had been around for so long and I'm sure Jake will give us "gyllenhaallics" a lot more movie pleasure for years to come.

March 14, 2014 | Unregistered CommenterJaragon

CMG-I was just going to point out that Nailed is probably number one on JA's movies-to-see, but he beat me to it by a post. I think we'd all like to have the ticket to that one, though. It could have Counselor level reviews and I'd still see it opening weekend.

March 14, 2014 | Unregistered CommenterJohn T

13 of 24... but haven't missed a non-Persia since Day After Tomorrow! Not bad, I say.

I <3 Jakie -- and I especially love that Jarhead poster. HOT

March 14, 2014 | Unregistered CommenterJake D

11. I have no words to describe my love for Brokeback Mountain. I also love The Good Girl and Donnie Darko. End of Watch was surprisingly good too.

I hated Love and Other Drugs. Thank God that was hist last attempt to become a teen heartthrob. I think he's a character actor with an amazing body, although I'm kind of worried because two months ago he was super slim and now he's muscled again. That can't be healthy.

March 14, 2014 | Unregistered CommenterPeggy Sue

yeah, love & other drugs was a major stinker but it's weird because both Jake & Annie were terrific in it but EVERYTHING else about it was just horrendous, from the script to direction to everything.

March 14, 2014 | Registered CommenterNATHANIEL R

Love and Other Drugs was the height of both their beauty (though maybe they'll surpass that?), so I highly recommend it for the eye candy alone.

I have seen nine of these movies. I watched October Sky when it came out and of course didn't know Jake G. Thank heavens I only thought he was a cute kid and didn't see the future hunkiness.

March 14, 2014 | Unregistered CommenterDave in Alamitos Beach

18 for me and I'm seeing Enemy this weekend. Most of what I have seen is his early stuff. I've seen everything since Moonlight Mile except Prisoners and that's in my Netflix queue.

Brokeback, October Sky, Source Code, The Day After Tomorrow (yes it's stupid but I love disaster movies)

Zodiac, Jarhead, Donnie Darko, Proof, Rendition, Brothers, Love and Other Drugs, Moonlight Mile

Bubble Boy, City Slickers, The Good Girl, Prince of Persia

End of Watch, Lovely and Amazing

March 14, 2014 | Unregistered Commenterjoel6

Oops, most of what I HAVEN'T seen is his early stuff. The one I'm most curious about is A Dangerous Woman but it's rarely shown.

March 14, 2014 | Unregistered Commenterjoel6

I've seen 13 and oh my, he has quite a few clunkers in there.

Although definitely not the most rangey actor out there and rarely the film's MVP, he's pretty dependable and I really enjoy some of his films/performances.

My favorite performances (in no order):
Brokeback Mountain
End of Watch (how great were Michael Pena and Jake in this? Unbelievable they didn't get more notices)

Film he most owes his career to:
Donnie Darko

Favorite Films:
Donnie Darko
Source Code

March 14, 2014 | Unregistered CommenterAnonny

What has jake got taped over his crotch in his butt photos????

March 14, 2014 | Unregistered CommenterMark

He took his acting to another level with Source Code. Nomination worthy performances in SC and Prisoners.

March 14, 2014 | Unregistered CommenterMB76

Eight. Grades.

A+: Donnie Darko
A: Brokeback Mountain
A-: Zodiac
B: October Sky, Bubble Boy
B-: Prisoners
C+: Prince of Persia: The Sands of Time
C: The Day After Tomorrow

March 14, 2014 | Unregistered CommenterVolvagia

I've seen 20 - City Slickers and everything since October Sky, which I saw in its original theatrical release. I had a major crush on him from OS on, so I've always considered myself a charter Gyllenhaalic. Favorites are Zodiac, Brokeback, Jarhead, and Lovely & Amazing. Really excited for Enemy.

March 14, 2014 | Unregistered CommenterRoark

Mark -- that's a "modesty pouch" that actors sometimes wear when they have nude scenes

March 14, 2014 | Registered CommenterNATHANIEL R

I've seen 7. Which is more than I usually have seen on these posterized things hahah.

Donnie Darko is definitely the best.

March 14, 2014 | Unregistered CommenterPhilip H.

I've seen 8, and loved only one (End of Watch). Jake doesn't really do it for me. I guess I've been to Gyllenholics Anonymous or something.

March 14, 2014 | Unregistered CommenterCarmen Sandiego

I've seen 8 and I'd say Zodiac is easily the best one. His best performance is probably in Brokeback Mountain though.

March 14, 2014 | Unregistered CommenterSean Troutman

Only seen five. I first became aware of him when Moonlight Mile was released. I could not get into Zodiac at all. He's very reliable but for me, nothing special. His nom for Brokeback Mountain is one of the worst category frauds ever.

March 14, 2014 | Unregistered Commenterbrookesboy

I've seen 20 of them, yeah ! Still have to watch : A Dangerous Woman, Josh and S.A.M., Homegrown and of course Enemy who isn't yet released in France. I'm a big fan since Donnie Darko, we have the same age Jake and me, and I follow his carrier since then, for his ups (Zodiac, Donnie Darko, Prisoners, Brokeback Mountain) and downs (Prince of Persia, Rendition) -less is better-. I've made my top on Mubi if you want to see, with a lot of pictures of him (https://mubi.com/lists/jake-gyllenhaal-top). I'm looking forward for his next movies, thrillers why not, but if he can made other movie styles, it's also good to me. I'm not very impatient to see the movie where he's very skinny, I'm not a big fan when the bodies are put to the test...

March 15, 2014 | Unregistered CommenterCaroline

I have seen 9.
Zodiac is a masterpiece
Brokeback Mountain is a masterpiece
Donnie Darko a very good movie
Source Code surprisingly good!
The Day After Tomorrow is pure disaster porn
Prince of Persia is his worst
Love and Other Drugs is ok
End of Watch was dizzying cause the camera moves made me green faced
Prisoners is such a hot mess and his character very 2D

March 15, 2014 | Unregistered CommenterManuel

I've seen about 3/4 of all of these (if you don't count anything before October Sky, which seems fair, I've seen nearly all) but it's mostly a mixed bag in terms of quality. I don't think he's ever turned in a horrid performance but some of those movies are definitely questionable.

I used to be a huge fan. The Dreamy Troubled Boyfriend Phase (2001-2002) phase is what did it. It was like a punch in the stomach. Those eyes! That smile! He was like every loner guy that I wish went to my high school so I could painfully lust after. Jarhead and Brokeback totally sealed the deal. His body in Jarhead is like WHAT. Incredible. Totally undervalued movie too. And Brokeback is Brokeback = dream bottom.

Also, Zodiac is cinematic perfection and he's plays such a good-natured Boy Scout type in that. Probably my fav of the three leads.

My love cooled somewhere around the Leading Man / Mixed Results (2010-2011) phase and has been on the decline since. Also, he dated Reese Pieces and ew, no. But good for him about working with Denis and taking more interesting roles. Still need to check out End of Watch.

BTW he's the sole reason I saw Highway, a total b-movie is ever there was but kinda fun ride, and The Day After Tomorrow, also kinda fun, where he played Dennis Quaid's son and shared a few scenes with him in that movie but many, many more in my dreams. Oh yes.

March 15, 2014 | Unregistered CommenterMark The First

I have seen 13, and hope to see all of them. There can never be enough Jake Gyllenhal.

March 16, 2014 | Unregistered CommenterBillinglsey

I've only seen 4 but Source Code is WAY underrated.

March 17, 2014 | Unregistered CommenterDeborah Lipp

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