Jake Gyllenhaal: Actor, Movie Star, Heart throb - WDW Guide Part I

One of the delights of Prince of Persia is that it's introduced a whole bunch of potential Gyllenhaalics-in-the-making to Jake Gyllenhaal. It's hard to see how anyone can resist but, nevertheless, it should be pointed out, that once one has dived into the cool nectar pool of Gyllenism, you won't want to pull the plug out. So, as a big welcome to all the new readers and commentors here at WDW, many of whom are now discovering Jake's earlier films for the first time, here is Part I of the WDW crib sheet to Jake Gyllenhaal's movies. Do feel free to disagree with my comments in the comment section )which may now actually be working...).


Title: City Slickers
Date: 1991
Role: Danny Robbins

Hotness: NA
Mascara-proof? Yes, unless you're really broody
Chemistry: NA
Hair: 5/10
Bonus features: Shoulder-popping

As a mere nipper, Jake Gyllenhaal semi-starred in the very successful film City Slickers as the attention-seeking, cute son of Billy Crystal, who left his father in no doubt that the only way he could ever be seen in public with him again is if he became a cowboy. As John Stewart once said, this was Jake's first cowboy movie, although, for me, this film will always be known to me as Blazing Saddles. I always get them muddled up. Billy Crystal has since said that Jake entertained the cast and crew with Show Tunes, heralding the beginning of Jake's side-career as set comic.



WDW rating: 8/10 (although that could be due to Blazing Saddles)

Title: October Sky
Date: 1999
Role: Homer Hickam

Hotness: Developing
Mascara-proof? Semi-waterproof mascara required
Chemistry: NA (although Laura Dern looked keen)
Sex scenes: NA (but Laura Dern looked keen)
Hair: 7/10
Bonus features: Good science and plenty of dirt

October Sky gave Jake his first lead role. Still at college and reading literary classics between scenes, Jake starred as a coal miner's lad who looked to the stars to avoid his fate beneath the ground. In this role, Jake made an astronaut who'd been to the moon cry. Without doubt, this is one of Jake's finest roles and I defy you to stay dry-eyed when the young Homer faces up to his fate and gets into that coal lift. This was the first effective use in a movie of Jake's blue eyes - a heart throb in the making and a fine actor to boot. One of my favourites.

WDW rating: 8/10


Title: Donnie Darko
Date: 2001
Role: Donnie Darko

Hotness: 5/10
Mascara-proof? No (although you may not understand why you're crying and it may be at the wrong bit)
Chemistry: 6/10 (Jenna Malone)
Hair: 7/10
Sex scenes: Donnie was too stressed
Bonus features: rabbits, smurfs, Halloween

The film that Jake is asked about more than any other, Donnie Darko is the most confusing film ever made and no one has a clue what it's about, including Richard Kelly, from whose mind it sprang, and Jake. It is quite possible that the only person who knows what's going on is an IT officer that I worked with in 2004. When prompted Jake can deliver some great transcendental background but the delight of Donnie Darko is that it doesn't really matter. The end is painful, heightened by Donnie's sister being played by Jake's sister, and Maggie has said that when filming the final scenes she and Jake kept apart to keep the emotion raw. The soundtrack is excellent - never has Duran Duran been used to such great effect. This film was not a 'commercial success' (it opened in the US just days after 9/11) but it continues to win over new fans and in the UK especially has been a big success. I can't think of any other film that can be argued over quite like this one or treasured quite like it. First of the great Jake commentaries.

WDW rating: 10/10


Title: Bubble Boy
Date: 2001
Role: Jimmy Livingston

Hotness: 2/10
Mascara-proof? No (father and son scenes are very moving)
Chemistry: 4/10 (Marley Shelton) Jake had a thing for Ever Carradine
Sex scenes: No sex before marriage
Hair: 0/10
Bonus features: underpants, Bubble Guinea Pig, dinosaurs

Nothing divides the modern world quite like Bubble Boy. At times Jake has defended it, at other times he's brushed over it. But, without doubt, no Jake film has the power to make my sides hurt with laughter like this one. The script is fantastic, Jake's delivery of those lines is spot on, the supporting actors - notably Swoosie Kurtz and John Carroll Fynch (who arguably appears in every Jake film ever made) - are fabulous. Other elements to relish include the Bright and Shiney people, Jimmy trying to buy a bus ticket and the stealing the beer scene. And the cow. 'And then Pinocchio came out of his plastic bubble and touched the filthy little whore next door and died. The End!' 'Supper time was the best! Nothing could beat Mom's homemade, vitamin-rich, soy-based, germ-free, fat-free fiber cookies.' Last but not least, Bubble Boy features my favourite Jake Gyllenhaal commentary: Jake and director Blair Hayes were made to be a double act. Some people think this film is rubbish - they are, of course, wrong.

WDW rating: 9/10


Title: Lovely & Amazing
Date: 2001
Role: Jordan

Hotness: 5/10
Mascara-proof? Yes
Chemistry: 5/10 (Catherine Keener)
Sex scenes: kiss in a car
Hair: 5/10
Bonus features: bad shirts, photography tips

Lovely & Amazing was the first in a stretch of films when Jake appeared as an older woman's lovetoy, plaything and sex object. The downside of this arrangement was that Jake did not appear in these films enough, with much of the attention focusing on the inner turmoil of the older woman in question. Meanwhile, Jake's character was left in the dark(room) quite a lot of the time. Catherine Keener was a great match for Jake here and, of course, they were later to team up again (although not romantically) in the film that may never be but one hopes it will be, Nailed. Not a bad film by any means, this film is, however, penalised as Jake wasn't in it very much.

WDW rating: 5/10


Title: The Good Girl
Date: 2002
Role: Possibly Holden

Hotness: 5/10
Mascara-proof? No
Chemistry: 9/10 (Jennifer Aniston)
Sex scenes: Yes (Jen's first)
Hair: 5/10
Bonus features: swimming, accents, car interiors

This is a film that grows on me whenever I see it, which, admittedly, isn't very much as I've only seen it twice. Again we have a film where Jake is taken under the wing of an older woman - although as the woman is Jen Aniston, this can hardly be seen as detrimental. This film isn't particularly light and should not be watched sober. It also had the peculiar side-effect of putting me off American shops for a while. Other people rave about this film. Other people also rave about Jake's hair in this film. This film does, though, have the potential of being a great tragedy (depending on how sober one is).

WDW rating: 6/10


Title: Highway
Date: 2002
Role: Pilot

Hotness: ?
Mascara-proof? ?
Chemistry: ?
Sex scenes: ?
Hair: ?
Bonus features: Goggles, alligators, glove puppets

How to describe Highway....? I can't, despite having seen it on a number of occasions, and therefore I called on the world's leading expert on Highway, Ruby, known throughout Jakedom for her 'Pilot thing'. And I quote: 'Jake's character is called Pilot! And he's the major old-school happener :D Pilot is adorable. John C McGinley plays a long-haired middle-aged stoner called Johnny the Fox. Piii-lot. He's adorable and sexually confused. Jake has a spider painted on his face. He's searching for the "once in a lifetime girl of my dreams and reason to believe" Pilot is adorable. It has an alligator boy. um.....Pilot is adorable.' And there you have it. I have to add that the eyes have it in Highway.

WDW rating: 6/10; Ruby rating: 10/10


Title: Moonlight Mile
Date: 2002
Role: Joe Nast

Hotness: 8/10
Mascara-proof: No. Don't wear it!
Chemistry: 10/10 (Ellen Pompeo)
Sex scenes: Hot
Hair: 5/10
Bonus features: New England scenery, post office, dog

Moonlight Mile marked a change in Jake's career. Still the young man, at the beck and call of his elders and betters, he nevertheless showed that he could hold a film tightly together and the camera loved him. Dustin Hoffman, Susan Sarandon and Holly Hunter - fine actors - and yet the camera loved Jake. This was Ellen Pompeo's break and the chemistry was bound to sizzle - her casting followed her encounter with Jake in an LA carpark when he told her that she was the most beautiful girl he'd ever seen. The power and emotion of Joe Nast's scenes are matched every step by the power and emotion of Bertie's. This film contains the most emotional of all Jake's lines for me - 'I lost my friend' - and I could wrap myself up in the big, comfy brown blanket that is Moonlight Mile and I would wallow in it. There's a strange mix here of suffocating brown earth and big blue sky - perfect.

Another great soundtrack (Rolling Stone's Moonlight Mile will tear your heart out) and another great commentary.

WDW Rating: 10+/10


End of Part 1: After Moonlight Mile, there could be little doubt that Jake Gyllenhaal was a name to watch (even if one couldn't spell it). No longer would he be the distraction in a story of women facing crises in their lives - Jake had a couple more steps to take and then he would be in the lead. I have no doubt that there are many who would disagree with some of my views above - so I would love to hear what you think.

Note: The films above are presented in IMDb order of release.

Includes pictures from IHJ. Thanks to Ruby for the Pilot input!