5. The Departed (2006)
Matt Damon plays a weaselly double-crossing cop in Martin Scorsese’s Oscar-winning mob classic The Departed, his character being an undercover mobster infiltrating the police force and misdirecting the investigation unit primed to take down mob boss Frank Costello (Jack Nicholson – The Shining).
Here, Damon plays opposite Jack Nicholson, Leonardo DiCaprio, Vera Farmiga, Martin Sheen, Alec Baldwin, Ray Winstone and an Oscar-nominated portrayal from Mark Wahlberg, yet excels as the film’s primary villain, his conviction being second to none as he flows and evolves with the twists and turns his character is faced with in this modern classic.
Now iconic for its many scenes of improvised dialogue, Scorsese’s only Best Director and Best Picture winning film, adapted from famous Hong Kong film Infernal Affairs, will have proved a test for Damon; one that he ultimately passed with flying colours.
4. Invictus (2009)
Based on the book “Playing the Enemy: Mandela and the Game that Made a Nation”, Clint Eastwood’s Invictus is set during Mandela’s first years as president of South Africa; a country struggling with the aftermath of the apartheid. Mandela, portrayed here by Morgan Freeman, sets out to unite the nation through the one passion all South African’s have in common: rugby. To do so, Mandela arranges a meeting with the captain of the national rugby team (known as the Springboks), Matt Damon’s Francois Pienaar, and from there an unlikely friendship is formed. With the encouragement of the president and influence from the multi-cultural crowd, the Springboks achieve the unachievable.
In Invictus, Matt Damon was pushed to his limits. Thanks to the extensive coaching and training of Chester Williams (a member of the winning team from the 1995 rugby world cup, who is also featured heavily in the film), Damon underwent a complete body transformation to make up for the size difference between himself and Pienaar, and the actor was tasked with adapting the ever-difficult South African accent too. In a moving and powerful performance, Damon shows Pienaar going through an emotional transition from failing rugby team captain to national treasure.
Damon gained a worthy nomination at the 2010 Academy Awards for Best Performance by an Actor in a Supporting Role for his performance in this beautiful film.
3. The Talented Mr. Ripley (1999)
The twists and turns of this film keep each of us on our toes from start to finish. This iconic feat in thriller cinema is glued together by its gutsy performances and stylish production.
Matt Damon plays title character Thomas Ripley, a lowly toilet attendant from New York, as he travels to the Italian Riviera to encourage the privately schooled Dickie Greenleaf (Jude Law) to return home to his long waiting parents. In the transition from grimy New York to idyllic Italy, Ripley makes the decision to replicate Greenleaf’s identity in a bid to experience life from the opposing side of society.
Damon is surrounded by a stellar cast which only encourages his stand out performance. Made up of the previously mentioned Jude Law, as well as Gwyneth Paltrow, Cate Blanchett and the great Phillip Seymour Hoffman, The Talented Mr. Ripley is a hotbed of performative excellence, of which Damon’s leading performance is a standout.
Damon’s portrayal of the desperate Thomas Ripley is at times understated and at times exaggerated, his use of quirky characteristics and an icy stare helping to build the uncomfortable experience felt whilst watching the film – this truly is an absolute must see for any Matt Damon check list.