List compiled by Eddie on 20/09/2024

One of the most diverse and consistent performers in the industry, Jake Gyllenhaal has been a Hollywood mainstay for multiple decades. 

While recently moving into more of a fun period where he’s been happy to take lead in the likes of Ambulance and Road House, there’s no denying that when Gyllenhaal wants to, he can match it with the best. 

Working with some of the modern era’s best filmmakers and collaborating with some of the world’s biggest and brightest stars, Gyllenhaal has always held his own and even at many times taken the spotlight with a series of turns that have often been awards worthy. 

With over 60 credits to his name, it’s not an easy task narrowing down Gyllenhaal’s top 10 but below is a list of some of his best work that should be proof enough of Gyllenhaal’s incredible talents and career. 

Happy reading, see you at the movies! 

10. Guy Ritchie’s The Covenant (2023) 

Gyllenhaal plays – Master Sergeant John Kinley

An unfortunate box office bomb, The Covenant saw Gyllenhaal lead a far better than expected Guy Ritchie film that is packed with thrilling action, supreme tension and likable characters. One of the best war films of recent memory, if you’ve previously passed on The Covenant it’s a film that’s well worth tracking down. 

Read my review here  

9. Jarhead (2005) 

Gyllenhaal plays – Anthony Swofford 

A divisive Sam Mendes film based of the experiences of real-life American soldier Anthony Swofford, Jarhead is a unique tale sent in the midst of the Gulf War and while not everything in Mendes film works, there’s a lot to like, including some stunning DOP by Roger Deakins and a typically solid Gyllenhaal lead. 

8. End of Watch (2012) 

Gyllenhaal plays – Brian Taylor 

Easily director David Ayer’s best film behind the camera, this gritty and intense police thriller that’s done doco-style is a pule-pounding affair that has become a huge audience favourite in the years since its initial release. A great pair up of Gyllenhaal and Michael Pena enhances a sometimes stereotypical genre film into something much more.   

7. Brokeback Mountain (2005) 

Gyllenhaal plays – Jack Twist

A film that needs no introduction and the film responsible for delivering Gyllenhaal’s only Oscar nomination at the time of writing, Brokeback Mountain broke new ground and launched its leads into the stratosphere with a tender drama that resonated with critics and audiences across the globe. 

6. Nocturnal Animals (2016)

Gyllenhaal plays – Tony Hastings/Edward Sheffield 

Sadly one of director Tom Ford’s two feature films, Nocturnal Animals is the type of film that may not make the biggest impact on first viewing but is one that sticks long in the mind as time wears on. Featuring a stellar cast and a moody atmosphere that includes a famous opening credits and a stunningly confronting abduction scene, Nocturnal Animals is a unique beast that is deserving of its cult status. 

Read my review here.  

5. Nightcrawler (2014)

Gyllenhaal plays – Louis Bloom 

Harbouring what is debatably Gyllenhaal’s best performance, Nightcrawler is an unforgettable unnerving experience that takes us on a wild and unpredictable ride into a seedy industry underbelly many would rather ignore. Delivering a creepy turn for the ages, Nightcrawler remains too this day a decade on a must-watch. 

Read my review here. 

4. Prisoners (2013) 

Gyllenhaal plays – Detective Loki

One of the modern eras most successful and unique thrillers that further established director Denis Villeneuve as a new age master, Prisoners is a fantastic example of Hollywood filmmaking and one that has grown in stature since its initially slept on release. 

Read my review here.  

3. Enemy (2013) 

Gyllenhaal plays – Adam and Anthony 

Perhaps a controversial pick near this section of such a list, Enemy remains one of the great undervalued works of both Gyllenhaal and his Prisoners director Denis Villeneuve. A twisting and turning psychological thriller with an unforgettable ending, one suspects that as time continues to move on, Enemy’s greatness will be better appreciated. 

Read my review here.  

2. Donnie Darko (2001) 

Gyllenhaal plays – Donnie Darko

A film that needs no introduction, Donnie Darko is the box office bomb that defied expectation to become one of the most indie films of all time that also saw many herald in director Richard Kelly as a once in a generational talent that has sadly come to be. A career making turn from Gyllenhaal is front and centre to a wild and totally unique deep dive into the unknown, ensuring Donnie Darko is a film unlike any other.  

1. Zodiac (2007) 

Gyllenhaal plays – Robert Graysmith 

A David Fincher masterpiece that is aging like a fine wine, Zodiac is an incredibly in-depth and stunningly realised investigational epic that stands heads and shoulders above most of its peers. Slept on when it first arrived in a crowded 2007 marketplace, Zodiac is arguably the most fully realised film of Fincher’s incredible C.V.   

Read my review here. 

What are your favourite Gyllenhaal movies? Let me know in the comments below!