Missed Oscartunities – Gyllenchella

While one of the biggest Missed Oscartunities for some Oscars and film lovers in recent history would be Jake Gyllenhaal’s incredible performance in Nightcrawler, for me his snubs at the Academy Awards go a bit further. Not only his loss for his supporting performance in Brokeback Mountain, but the fact that his performance in the Ang Lee drama is his only nomination in a career filled with stunning, powerful performances.

Instead of giving you my personal opinion, I wanted to take it to the polls and see where everyone landed on Gyllenhaal’s performances…what is his best performance in a career that took off after his leading role in October Sky in 1999? We did four rounds via polls on our Twitter for Gyllenchella. Each round delivered surprising results, but also some obvious winners. Here is how each round went down below.

Round One:

Prisoners vs The Guilty
Two extremely heavy films with powerful performances from Gyllenhaal in cop centric jobs, but extremely different performances and films.

Prisoners was released Thanksgiving weekend in 2013 (ya know a family film!) and co-stars Hugh Jackman, Paul Dano, Viola Davis, Maria Bello and Melissa Leo. Sadly, the Denis Villeneuve film only received one Oscar nomination, but is regarded by most as one of Gyllenhaal’s best films in his filmography.

The Guilty, one of the first pandemic productions, was released in 2021 by Netflix. The remake of the Danish film of the same name was directed by Antoine Fuqua. The film has a minimal on screen cast as it focuses on Gyllenhaal’s character as a 911 call center operator. Peter Sarsgaard, Gyllenhaal’s brother-in-law, voices one of the characters. Paul Dano, his co-star from Prisoners, voices another character.

Prisoners won out this round with 95% of the 199 votes.

The Sisters Brothers vs Spider-man: Far from Home
Editor’s Note: The results of this poll deeply upset me and I will be reporting everyone who voted against The Sisters Brothers to Detective Loki.

The Sisters Brothers is an adaptation of a novel by the same name. The film co-stars Joaquin Phoenix, John C. Reilly and Riz Ahmed. The Western is the first English-language film by director Jacques Audiard.

Spider-man: Far from Home is the second installment in the Spider-man trilogy starring Zendaya and Tom Holland. Gyllenhaal plays the villain in this film. Listen, personally, I know nothing about this film other than that.

Spider-man: Far from Home won this round with 53% of the 177 votes.

Velvet Buzzsaw vs Okja
Velvet Buzzsaw reteamed Gyllenhaal with writer/director Dan Gilroy and Rene Russo (we’ll get into their previous collaboration a bit later). The satire film set in the contemporary art world was released on Netflix in 2019. The film has a large ensemble including Toni Collette, Natalia Dyer, Daveed Diggs and John Malkovich.

Okja, also released on Netflix, was written and directed by Bong Joon Ho. The film stars Tilda Swinton, Paul Dano, Seo-hyun Ahn, Lily Collins and more. A heartbreaking film that shows Gyllenhaal in such a eccentric role, that many IMDb users think is his worst, but personally, I think it’s one of his best. Spoiler for the poll: apparently, majority of you agree with me!

Okja won with 71% of the 184 votes.

Stronger vs Wildlife
Stronger is a harrowing, inspiring real story of Jeff Bauman, who survived the Boston Marathon bombing. Based on Bauman’s memoir, the film follows Bauman after he loses his legs in the Boston Marathon bombing and adjusts to his new life.

Wildlife is based on a novel of the same name and directed by Paul Dano, a frequent Gyllenhaal co-star! The film co-stars Carey Mulligan, Ed Oxenbould and Bill Camp. The film follows Joe, a teenage boy, as he navigates his mother’s response to his father leaving their home for a job.

Stronger won with 60% of the 173 votes.

Nocturnal Animals vs Demolition
Nocturnal Animals is the second feature film directed by Tom Ford and was released in 2016. The film co-stars Amy Adams, Michael Shannon, Aaron Taylor-Johnson and Laura Linney. The film straddles between a novel and real-life with, bonus points, Gyllenhaal playing two characters.

Demolition pairs Gyllenhaal with Jean-Marc Vallée directing him alongside Naomi Watts and Chris Cooper. Gyllenhaal plays an investment banker struggling with losing someone close to him and follows him as he forms a friendship with a customer service rep and her son.

Nocturnal Animals won the poll with 82% of the 174 votes.

Enemy vs Southpaw
Enemy once again paired Gyllenhaal with Denis Villeneuve in a 2013 thriller film. The film follows Gyllenhaal as he seeks out his lookalike after spotting them in a movie. Bonus points again, Gyllenhaal plays two characters in this film!

Southpaw follows Gyllenhaal as a boxer in the aftermath of a fatal accident. The film directed by Antoine Fuqua co-stars Rachel McAdams, Forest Whitaker and Oona Laurence. The film was written by Kurt Sutter, who created Sons of Anarchy.

Enemy won the poll with 59% of the 170 votes.

Nightcrawler vs End of Watch
Nightcrawler is a crime thriller that, personally I believe is an all-timer for LA films. The film follows Gyllenhaal as Louis Bloom as he graduates from thief to crime journalist to well…a criminal. The film was written and directed by Dan Gilroy and co-stars Riz Ahmed, Bill Paxton and Rene Russo.

End of Watch is a documentary style shot film starring Gyllenhaal as an LAPD officer alongside Michael Peña. The film was directed and written by David Ayer and co-stars America Ferrera and Anna Kendrick.

Nightcrawler won the poll with 95% of the 200 votes.

Zodiac vs Brothers
Zodiac is an all timer for many of us. The film was released in one of the best years of modern cinema, 2007, and was directed by David Fincher. The film is based on the book about the Zodiac killer written by Robert Graysmith, who Gyllenhaal plays. The film co-stars Robert Downey Jr., Mark Ruffalo, Brian Cox and John Carroll Lynch.

Brothers was released in 2009 and directed by Jim Sheridan. The film follows Natalie Portman whose husband, played by Tobey Maguire, is believed to have died in Afghanistan and her brother-in-law, played by Gyllenhaal consoles her only to see her husband return home after all.

Zodiac won the poll with 87% of the 190 votes.

Jarhead vs The Good Girl
Jarhead, directed by Sam Mendes, was released in 2007 and co-stars Jamie Foxx, Lucas Black and Peter Sarsgaard, Gyllenhaal’s brother-in-law! Told through the eyes of a Marine sniper, the film follows his mindset during the Golf war.

The Good Girl, written by Mike White, co-stars Jennifer Aniston, John C. Reilly and Deborah Rush. Gyllenhaal’s character strikes up a relationship Aniston’s while working at a discount store. The film has an insane cast (John Carroll Lynch, Zooey Deschanel, Tim Blake Nelson and Mike White himself!)

Jarhead won the poll with 82% of the 155 votes.

Brokeback Mountain vs Love & Other Drugs
Brokeback Mountain was released in 2005 and co-stars Heath Ledger, Anne Hathaway and Michelle Williams. The film follows Gyllenhaal and Ledger as two shepherds who develop an emotional connection and begin an affair.

Love & Other Drugs also co-stars Anne Hathaway and was released in 2010. The film follows Gyllenhaal as a medicine rep as he starts a relationship with a young woman suffering from Parkinson’s disease.
Brokeback Mountain won the poll with 89% of the 200 votes.

Bubble Boy vs The Day After Tomorrow
Bubble Boy was actually released in the same year as another Gyllenhaal starring film, but has much different vibes. Bubble Boy follows Gyllenhaal as Jimmy, who was born with no immune system and literally lives in a bubble. Another Gyllenhaal film with John Carroll Lynch!

The Day After Tomorrow was released in 2004 and somehow does not star Gerard Butler in this weather “bad storm killing the earth” film. The film co-stars Dennis Quaid, Emmy Rossum and Dash Mihok.

The Day After Tomorrow won the poll with 69% of the 166 votes.

Donnie Darko vs October Sky
Donnie Darko is for what many put Gyllenhaal on their radar. For some, it was their first film with the actor. The film follows Gyllenhaal as a troubled teenager navigating his life after a bizarre accident. The film has an amazing cast including Jena Malone, Maggie Gyllenhaal, Patrick Swayze, Drew Barrymore and Ashley Tisdale.

October Sky is a staple for some people like me…I lost track, personally, of how many times I watched this film in school. Released in 1999 based on a true story, the film follows a coal miner’s son who was inspired by the first Sputnik launch to take up rocketry against his father’s wishes. The film co-stars Laura Dern and Chris Cooper.

Donnie Darko won the poll with 85% of the 185 votes.

Round Two:

Prisoners vs Spider-man: Far From Home
Prisoners won 85% of the vote.

Okja vs Stronger
Okja won 55% of the vote.

Nocturnal Animals vs Enemy
Nocturnal Animals won 56% of the vote.

Nightcrawler vs Zodiac
Nightcrawler won 89% of the vote.

Brokeback Mountain vs Jarhead
Brokeback Mountain won 95% of the vote.

Donnie Darko vs The Day After Tomorrow
Donnie Darko won 71% of the vote.

Round Three:

Prisoners vs Okja
Prisoners won 86% of the vote.

Nocturnal Animals vs Nightcrawler
Nightcrawler won 79% of the vote.

Brokeback Mountain vs Donnie Darko
Brokeback Mountain won 90% of the vote.

Bonus Round for the Social Media Intern who did their Math Wrong:

Stronger vs John Mulaney & the Sack Lunch Bunch
Stronger won the poll with 56% of the vote.

Round Four:

Prisoners vs Nightcrawler
Nightcrawler won with 63% of the vote.

Stronger vs Brokeback Mountain
Brokeback Mountain won with 86% of the vote.

To be honest, this was the showdown we all saw coming. These are two of Gyllenhaal’s best performances in a career filled with incredible performances.

Nightcrawler vs Brokeback Mountain
Nightcrawler won with 54% of the votes.

We had so much fun with Gyllenchella and hope you did as well! We have fun similar events planned in the future, but if there’s any actor, director, writer or anyone in the film industry you want us to focus on, let us know!

In case this list inspired you to watch more of Gyllenhaal’s films, click here for a list of all the films from Gyllenchella and where they are available to watch!

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