Jake Gyllenhaal's best movie roles

We take a look back over the career of the NIGHTCRAWLER star…

NIGHTCRAWLER is released in Irish cinemas this week, and stars Jake Gyllenhaal as a young man determined to become a broadcast video journalist, no matter the cost. Gyllenhaal gives a stellar performance in NIGHTCRAWLER, making the film one of 2014’s strongest, so we decided to take a look back over the career of the film’s star…


Although he had made appearances in films in the 1990s – including a small part in CITY SLICKERS – Gyllenhaal truly caught audiences’ attention with the 2001 film DONNIE DARKO. Playing a disturbed young man who is convinced that the world will end at a predetermined time, and whose best friend is an imaginary rabbit named Frank, Gyllenhaal quickly proved himself a capable and engaging actor.
DONNIE DARKO twists and turns, often taking unexpected narrative paths, but it is Gyllenhaal’s performance as the disturbed but curious, romantic and ungrounded Donnie that holds the film together, and proved the Gyllenhaal was a name to watch out for.


A film not often mentioned when it comes to Gyllenhaal is his follow up to DONNIE DARKO, the odd, quirky and offbeat comedy BUBBLE BOY. Gyllenhaal plays Jimmy Livingston, a boy born without an immune system who has lived his entire life in a specially designed plastic bubble, to keep him from illness and infection. When the love of his life Chloe (Marley Shelton) announces she is going to Niagara Falls to marry her boyfriend, Jimmy decides to take matters – and his health – into his own hands, and sets out on a journey to stop the wedding.
OK, so BUBBLE BOY is not actually a great film, and yes, there are times when the film stumbles into offensive territory, but Jake Gyllenhaal’s performance – all wide eyes and innocence – is the heart and soul of the film, and the proof that there is more to this actor than dark and brooding roles. BUBBLE BOY was a box office flop, but Gyllenhaal’s performance is endearing and sweet, and shows his range.


Returning to the world of drama, Gyllenhaal starred opposite Heath Ledger in 2006’s BROKEBACK MOUNTAIN. Gyllenhaal plays Jack Twist, a man hired to herd sheep through the Wyoming mountains with Ennis Del Mar (Heath Ledger). In the time they spend on the isolated mountain, the two men form a deep emotional bind, which gives way to an intense sexual relationship.
Both Gyllenhaal and Ledger were Oscar nominated for their performances, with Gyllenhaal’s work being praised by critics and fans a like, for the deep reserves of emotion and recklessness that he brought to the role, and the on-screen chemistry he created with Heath Ledger.


Starring Jennifer Aniston as a small town woman disillusioned with her life, and written by Mike White, THE GOOD GIRL is the story of two people in a small town who are drawn together due to mutual boredom and borderline despair.
Gyllenhaal has the smaller of the two lead roles in THE GOOD GIRL, but once again plays a role that is emotionally engaging, and slightly manic. Holden is a young man who believes the lies he tells about himself, and dreams of being like his hero, Holden Caulfield from Catcher in the Rye.
THE GOOD GIRL is a dark, satirical and tragic look at the world of a small town, and people whose lives haven’t amounted to much. Gyllenhaal shows off his creepy, manic and oddly touching sides, as a young man whose life is entangled in the myths of his mind.


When Keller Dover’s (Hugh Jackman) daughter and her friend go missing, he takes matters into his own hands, even as Detective Loki (Gyllenhaal) chases down every lead to find the girls before it’s too late.
On the surface, it seems as though PRISONERS is yet another police procedural, and another film in which all characters are as dark as they are painted. Not so Jake Gyllenhaal’s Detective Loki, a good man, good cop and tenacious investigator who is drawn into a seemingly simple case of missing people. Gyllenhaal’s performance threatens to steal the show in PRISONERS, as he makes Loki a vulnerable yet commanding presence at the heart of the story, and the one who grounds the chaos of the investigation.

Honourable mentions to: JARHEAD, END OF WATCH and BROTHERS.

Do you have a favourite Jake Gyllenhaal movie? Let us know in the comments below.

NIGHTCRAWLER is released in Irish cinemas on October 31st 2014

Words: Brogen Hayes