Quentin Tarantino’s latest film Once Upon A Time… In Hollywood arrives in cinemas this week, and it has an all star cast headlined by Brad Pitt and Leonardo DiCaprio. I decided to dive into the careers of these two exceptional actors and pick my favourite films from their illustrious filmographies. As always these lists are just opinion, and I’d love to hear your favourites in the comments.

Number 5:

  • Brad Pitt: 12 Years A Slave – Not only did Pitt have a role in 12 Years A Slave he was one of the major producers on the film, indeed he has been at the forefront of giving a lot of minority filmmakers a platform to share their voice and vision. Such was the case with Steve McQueen’s raw and incredibly emotional 12 Years A Slave. This was such a powerful story, so beautifully told, with so many exceptional performances. Pitt may have only been a small player in the actual story of the film, but he deserves to be recognised for his work behind the scenes.
  • Leonardo DiCaprio: Django Unchained – I didn’t love Django Unchained, I think it is one of Tarantino’s weaker films (that still makes a very good film mind you). However you cannot question just how great DiCaprio was as the villainous Calvin Candie. He’s intimidating and despicable, yet completely captivating every moment that he’s on screen, and great foil for Christoph Waltz’s Dr King Schultz.

Number 4:

  • Brad Pitt: Se7en – Se7en is one of David Fincher’s absolute best films, featuring at its core two wonderful performances from Pitt and Morgan Freeman. The film is a neo-noir crime film, but is elevated beyond that by Fincher’s masterful touch and the leading performances. Pitt’s Detective Mills is the emotional heart of the film, playing off Freeman’s more jaded DL Somerset expertly. And his final moments in the film when John Doe’s true plan is revealed are some of the best of Pitt’s illustrious career.
  • Leonardo DiCaprio: The Wolf of Wall Street – Martin Scorsese and DiCaprio have worked together numerous times throughout the 21st century, but nowhere does Leo shine brighter than in The Wolf of Wall Street. He has the magnetism and charisma to make you understand how Jordan Belfort was able to pull off everything he did, and why so many people went with him. But he’s also able to show just how vile and horrible Belfort was at the same time. It is truly a tour de force performance from DiCaprio, particularly the quaaludes scene.

Number 3:

  • Brad Pitt: Ocean’s Eleven – A remake that improves upon the original, Steven Soderbergh’s version of Ocean’s Eleven is as close to the perfect heist movie as you are going to get. The film has a big over the top con at its heart that keeps you guessing until you see the reveals, and just has fun every second of the way. With Pitt playing alongside George Clooney, two of the potentially biggest stars of the era, the pair have fantastic chemistry, and lead the ensemble cast whilst setting the perfect tone for the film.
  • Leonardo DiCaprio: Catch Me If You Can – DiCaprio has worked with a huge number of incredible directors over the years (just look at who we’ve already had represented in this list) and that includes the master, Steven Spielberg, with one of his best films of the 2000s, Catch Me If You Can. Playing the young con man Frank Abagnale Jr., DiCaprio brings such heart to the character, who could easily be unlikeable, but he forces you to sympathise with this lonely character. His cat and mouse chemistry with Tom Hanks is great, and helped to show that DiCaprio was more than just a heartthrob.

Number 2:

  • Brad Pitt: Snatch – Guy Ritchie’s Snatch is a fantastic British Crime caper with a sprawling ensemble cast. The one who steals every scene he’s in is Brad Pitt as Mickey, an Irish traveler bare-knuckle boxing champion. In the film Mickey is deliberately completely unintelligible, possibly in response to people complaining about the accents in Lock, Stock and Two Smoking Barrels, but whatever the reason it lead to one of the funniest performances you’ll see in the 21st Century.
  • Leonardo DiCaprio: Gangs of New York – This may be a controversial one, but Gangs of New York is still my favourite Scorsese film to this day. Sure DiCaprio isn’t the one who steals every scene, that honour goes to Daniel Day Lewis as Bill ‘the Butcher’ Cutting, but this was the film that started the partnership between DiCaprio and Scorsese. The film is a such an epic period drama, but it is rooted in this war between these two individuals, and that gives it so much more in the way of emotional stakes than most period epics.

Number 1:

  • Brad Pitt: Inglourious Basterds – Pitt’s previous appearance in a Tarantino film might well be summed up for both of them by the film’s final line “this might just be my masterpiece”. Pitt plays the leader of the Basterds, Lieutenant Aldo Raine, and is exceptional in this huge over the top role. As an intimidating force as the head of the Basterds Pitt is great, but it is comedic delivery that might make this his best performance. It doesn’t hurt that it is one of the best films ever made.
  • Leonardo DiCaprio: Inception – But for me DiCaprio’s best film is his 2010 collaboration with Christopher Nolan, Inception. This is a film that was so groundbreaking and epic in its ideas and the effects that it brought to the screen, but never lost sight of that very human family story at its core. And without an actor of the talent of DiCaprio playing Cobb that could have been lost amid these dreams. What we learn of his relationship with his late wife is heartbreaking, and is fittingly the small scale finale of such an epic film. Not only is this the best film of DiCaprio’s career, but his performance is right up with his more bombastic, award winning ones.