At only 34 years old but with a substantial body of work behind him it feels like Jake Gyllenhaal is a seasoned pro who is somehow only just getting started. From his breakout role in cult classic Donnie Darko to his Oscar nomination in Brokeback Mountain, Gyllenhaal has established himself as one of the most soulful and talented actors working today, and now he’s stepping in another direction with a punishing lead role in boxing drama Southpaw.

It’s a long way from where he started. His first film role was as Billy Crystal’s son in City Slickers (1991) and it was followed by a few more in his teenage years, including an appearance on Homicide: Life on the Streets, David Simon’s precursor to The Wire (the greatest TV show ever made? Discuss). Despite these early successes, it wasn’t until 2001 that he found the first defining film of his career with his lead role in Donnie Darko. Starring alongside his sister Maggie, he is the perfect lead for Richard Kelly’s enigmatic, disquieting teen drama. The film’s lo-fi sci-fi stylings rely on a gathering sense of dread and an understanding of what it feels like to be an outsider that chimed with teen audiences in particular.

Donnie Darko established him as a face to remember for a generation, and Gyllenhaal was almost cast in a role that would have risked pigeonholing him for years to come. His close friend Tobey Maguire had starred in the first Spider-Man film, but later sustained a back injury which threatened his participation in the sequel. The producers were keen to cash in and start shooting quickly after Spider-Man’s success, but in the end Maguire recovered enough to resume arguably his most famous role.

Gyllenhaal would have made a great Spider-Man, but looking back at his career with the benefit of hindsight, the more commercial world of superhero blockbusters doesn’t seem to fit with his strengths. Indeed, his only foray towards that style of film – Prince of Persia: The Sands of Time – was also his biggest failure. The sooner it’s lost to the – ahem – sands of time, the better.

Instead, he earned his first – and so far only – Oscar nomination as a gay cowboy opposite Heath Ledger in Ang Lee’s Brokeback Mountain (2005). This tender and heart-breaking performance was followed by another in Jarhead that focused more on the physical than the emotional. Directed by Sam Mendes, Gyllenhaal played a sniper in the US Marines dealing with the chaos and sometimes the boredom of war. It was another strong performance in a very promising career, and he followed it two years later with an appearance for one of the best directors of recent times: David Fincher.

Zodiac was the result. It often gets overlooked alongside Fincher’s early hits, Se7en and Fight Club, or his later classics, The Social Network and Gone Girl, but Zodiac deserves to stand proudly beside them. The film is slow and methodical, just like the serial killer investigation it focuses on, so a lot rested on the shoulders of the cast, led by Gyllenhaal and supported by Robert Downey Jr. and Mark Ruffalo. It’s safe to say he knocks it out the park, with a performance that captures the desperate compulsion to unpick a mystery as well as the growing fear of a man who begins as a political cartoonist and soon finds himself at risk from a violent and deadly serial killer.

Further roles in thought-provoking sci-fi Source Code (2011) and the frenetic End of Watch (2012) continued Gyllenhaal’s run of form, though it’s hard to think of many occasions where he’s given a ‘bad’ performance. His recent collaborations with Denis Villeneuve – Prisoners and Enemy – have also proved fruitful and challenging, full of the dark material on which Gyllenhaal has made his name. His biggest success and disappointment though, surely has to be his sickening turn in 2014’s Nightcrawler.

As self-taught media psychopath Lou Bloom, he is more slimy than slick – an entrepreneurial creep who buys a camcorder and begins filming the victims of car crashes and murders around L.A. The film is a pitch-black satire on the destructive nature of modern media and whilst the direction, writing and supporting cast are all excellent, the film lives or dies on its lead performance. It is the greatest achievement of Gyllenhaal’s career to craft a character so disgusting and unsympathetic, but still make him, if nothing else, admirable. Nightcrawler was one of the best films of 2014 and his lead performance should have won Jake Gyllenhaal an Oscar.

Early hype is suggesting that this might finally be his year. The reviews for Southpaw are average, but his performance has been unanimously lauded and if there’s one thing the Academy loves, it’s a showstopping physical transformation. Even if the film doesn’t prove popular enough to help him to another nomination, you can’t help feeling there’ll be plenty more chances to come. And anyway, there’s more to life than Oscars. No matter how big the statuette-shaped space on his mantelpiece, there’s no doubt that Jake Gyllenhaal is one of the best actors in the business right now.