5. Zodiac (David Fincher, 2007)
The much acclaimed thriller from renowned director David Fincher features fine performances not only from Gyllenhaal but also from Robert Downey Jr. and Mark Ruffalo.
In this fact based film centering on an infamous serial killer, the actor plays a nerdy San Francisco cartoonist who becomes obsessed with the activities and identity of a mysterious serial-killer named Zodiac. Robert Graysmith (Gyllenhaal) becomes involved in the massive investigation concerning the killer, becoming a wannabe detective in the pursuit of Zodiac.
This excellent film adapted from a book written by the real Graysmith allows the actor to develop his character in excellent detail.
4. Prisoners (Denis Villeneuve, 2013)
Denis Villeneuve, the director of Enemy, which also starred Gyllenhaal, similarly cast him in a major role in this film. Despite a running time of almost two and a half hours,the performances of the actor and co-star Hugh Jackman make this time well spent.
Keller Dover (Jackman) is the father of one of a pair of missing girls (Maria Bello plays the mother and wife of the family). Viola Davis and Terrence Howard play the parents of the other girl.
Both couples invest their hopes for finding their daughters in detective Loki (Gyllenhaal), an eccentric cop who has never failed in any of his previous cases. Paul Dano plays a man who seems to be the kidnapper of the children and, after he is released from custody, Keller tries to find out the truth by his own methods.
3. Donnie Darko (Richard Kelly, 2001)
This unusual film directed by Richard Kelly exerts a haunting quality. This was an overlooked movie in 2001 but has developed into a cult movie in recent years.
This is still one of the actor’s signature roles. Gyllenhaal plays Donnie, a high-school eccentric student who communicates with a giant rabbit named Frank who dispenses apocalypse prophesies. He also co-stars with his sister Maggie playing a brother and sister.
2. Brokeback Mountain (Ang Lee, 2005)
Brokeback Mountain is a magnum opus in the career of this actor. This Ang Lee’s adaptation of E. Annie Proulx’s story resulted in 8 Oscar nominations (winning three of them) including the one for Best Supporting Actor for Gyllenhaal.
This “unorthodox” western movie isn’t really about cowboys, or about a gay relationship as it tells the story Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal). The film relates a story about two human beings falling in love with each other, who happen to be two men who develop something far deeper than simple friendship.
Both leads give mesmerizing performances playing male lovers who also have families and children they love, causing them keep their relationship a secret with one another. Brokeback Mountain remains one of the actor’s best efforts.
1. Nightcrawler (Dan Gilroy, 2014)
Largely overlooked, Nightcrawler was a pleasant surprise and one of the notable films of 2014, not only due to Gyllenhaal’s performance but also the work of Riz Ahmed and Rene Russo.
Nightcrawler draws from the dichotomy of richly delineating a character as that character disintegrates as a human being thanks to limitless ambition. Lou Bloom (Gyllenhaal’s character) is a detached and empty freelance videographer who starts to find the line between illusion and reality blurring, an effect which extends to the audience.
Nightcrawler takes a critical look at the media and is also a satire of journalists’ ethics. Gyllenhaal assumes the mantle of Lou Bloom masterfully by transmitting a palpable lack of empathy and emotional connection with the others highlighted late in the film as Lou films his dying partner Rick instead of trying to help him, rendering only a blank, empty person as Lou continues his ascension in order to keep “winning” (the only thing that matters to him) with no clue as to what he will do next.
Author Bio: João Vieira is a cinema aficionado since he can recall. His favorite director is Woody Allen and he likes to watch movies from all genres, years and countries. In his spare time you’ll probably see him reading a book or talking with his friends about a movie or series he just saw.