In forty-three years, thirty feature films and more than two hundred and fifty award nominations, Leonardo DiCaprio has established himself as one of the greatest actors – if not the greatest actor – of his generation. Among the audience and critics there is practically no talk about his performing talent.
Having collaborated with Martin Scorsese, Baz Luhrmann, Quentin Tarantino, Robert De Niro, Steven Spielberg, Christopher Nolan and Clint Eastwood, very few actors possess the same career diversity as DiCaprio. His rise from teen idol to self-taught dramatic comedian has resulted in a long string of creative and financial gains, remaining reliable since his first appearance in a feature film.
ten Tobias “Toby” Wolff in This Boy’s Life (1993)
According to the memoirs written by Tobias Wolff, This boy’s life is directed by Michael Caton-Jones. Starring Leonardo DiCaprio as Tobias “Toby” Wolff, the film also features supporting performances from Robert De Niro, Ellen Barkin, Chris Cooper, Carla Gugino and Tobey Maguire (in his feature debut).
DiCaprio’s breakthrough role as Toby in This boy’s life is sharp, believable and undeniably moving. He steals the show with his performance, creating a character that survives childhood trauma through his independence and creativity. De Niro and DiCaprio clash on several occasions – and it’s a testament to the latter’s talent that he manages to feel as big as the former.
9 Amsterdam Vallon in Gangs of New York (2002)
Based on Herbert Asbury’s 1927 non-fiction novel of the same name, New York Gangs follows a group of Irish immigrants protesting low wages amid a long-running Catholic-Protestant feud that escalates into violence. Leonardo DiCaprio stars as Amsterdam Vallon with a supporting performance from Daniel Day-Lewis.
Scorsese creates a spectacular period piece, spotting subtle political dots along the way to demonstrate his mastery as a director. Each scene is loaded with exquisite cinematography and production design, enhanced by gritty performances from the entire cast. DiCaprio puts on a phenomenal performance as a young Irish immigrant, with equally enigmatic work from Day-Lewis giving an electrifying portrayal of William Poole as Bill “The Butcher” Cutting.
8 Frank William Abagnale Jr. in Catch Me If You Can (2002)
Directed by Steven Spielberg, Catch Me If You Can is based on the autobiography of Frank William Abagnale Jr. (played by DiCaprio), who allegedly cheated millions of dollars by posing as a Louisiana parish attorney, a practicing physician in Georgia, and a Pan American World Airways pilot .
Part fantasy, part crime thriller, part comedy, part Bond movie; Catch Me If You Can cements Spielberg as one of the greatest directors of the 21st century. DiCaprio’s performance is charming, intriguing, calculated and elegant. He conducts himself with incredible charisma, winning over everyone he meets with his deceptively endearing manipulation tactics.
seven Howard Hughes in The Aviator (2004)
Directed by Martin Scorsese, the aviator depicts the life of Howard Hughes (DiCaprio), an aviation pioneer and film director Angels of Hell. Spanning 20 years between 1927 and 1947, the film explores how Hughes became reclusive due to his Obsessive-Compulsive Disorder (OCD).
Scorsese’s first collaboration with DiCaprio heralded a true artistic union between the two, allowing DiCaprio to establish himself as one of the greatest actors of his generation. Surrounded by fantastic supporting talent, DiCaprio brings to life the candor and brashness of an aviation enthusiast and engineer, and the struggles of living with OCD.
6 Hugh Glass in The Ghost (2015)
Directed and co-written by Alejandro G. Iñárritu, The ghost is based on Michael Punke’s 2002 novel of the same name, adapted from the 1915 poem The Song of Hugh Glass. Starring Leonardo DiCaprio as Hugh Glass, the film chronicles his experiences as a pioneer through the territory of what is now North and South Dakota in 1823.
DiCaprio’s performance is raw, realistic and revealing. His turn as Hugh Glass is incredibly focused, enhanced by stellar supporting performances – especially Tom Hardy’s turn as the film’s antagonist, John Fitzgerald. Director Iñárritu makes a visually stunning film that turns into an exploration of human consciousness. DiCaprio’s dedication to the character earned him his first Academy Award for Best Actor in a Leading Role at the 88th Academy Awards in 2016.
5 Deputy Marshal Teddy Daniels at Shutter Island (2010)
Leonardo DiCaprio stars as Deputy Marshal Teddy Daniels in Martin Scorsese shutter island. The film follows an investigation into a mental institution off Boston Harbor, located on a remote, windswept island, which raises the question of a patient’s unlikely disappearance. For all the haunting imagery and clever storytelling, shutter island represents Martin Scorsese at his best.
DiCaprio gives an unapologetically thrilling performance in his depiction of grief and tragedy, heightening every emotion of presumed truth with maximum psychic fear and confusion. Blending the neo-noir components of classic cinema with the psychological elements of modern cinema, Shutter Island is a masterfully crafted mystery/thriller.
4 Rick Dalton in Once Upon a Time…in Hollywood (2019)
Directed by Quentin Tarantino, Once upon a time… in Hollywood follows the life of Rick Dalton (DiCaprio), a declining actor who, along with his stunt double (Brad Pitt), navigates the rapidly changing film industry in 1960s Hollywood.
In a movie that exists between the line of fact and fiction, Rick is the character that holds it all together. DiCaprio plays him with an undeniable charm and confidence that makes the character and his story honest every step of the way. Once upon a time… in Hollywood features an ensemble cast with multiple storylines and plays like a modern fairy tale homage to the final moments of Hollywood’s Golden Age.
3 Arnie Grape in What’s Eating Gilbert Grape (1993)
Directed by Lasse Hallström, What eats Gilbert Grapefollows the story of Gilbert Grape (Johnny Depp), who cares for his obese mother and younger brother, Arnie (DiCaprio), who has autism spectrum disorder (ASC).
What eats Gilbert Raisin is one of DiCaprio’s first films and marks the first time he was nominated for an Oscar. His performance is tremendous. Director Hallström balances a bittersweet tone in this dysfunctional family tale, suggesting that the real heroes in life are those who care for others with tenacity, determination and, above all, love.
2 Calvin J. Candie in Django Unchained (2012)
Directed by Quentin Tarantino, Django Unchained follows Jamie Foxx in the lead role of a slave who trains under the mentorship of a German bounty hunter (Christoph Waltz). Leonardo DiCaprio plays Calvin J. Candie, a wealthy slaver who owns a plantation in Mississippi called “Candyland”, a place where Django’s wife Broomhilda (Kerrie Washington) resides.
In an interview with Playboy, Tarantino admitted:[Calvin J. Candie] is the first villain I wrote that I didn’t like. I hated Candie and I normally like my villains no matter how bad they are.“DiCaprio’s performance makes him one of the vilest and most repulsive antagonists in Tarantino’s catalog of characters. There’s a country, theatrical eccentricity to the delivery of DiCaprio’s line, which makes for a climactic outburst of Candie during the dinner scene all the more shocking and disconcerting.
1 Jordan Belfort in The Wolf of Wall Street (2013)
Directed by Martin Scorsese, The Wall Street Wall tells the true story of stockbroker Jordan Belfort (DiCaprio), who made millions defrauding wealthy investors in the 1990s. After partaking in a hedonistic brew of debauchery and excess, the empire de Belfort collapses at the hands of the FBI and the SEC.
Leonardo DiCaprio delivers a powerful performance as Belfort, launching the character with swaggering and salacious one-liners. Skating on the fine line between the deplorable and the hysterical, his performance is never anything less than magnetic. Nominated for Best Lead Actor at the 86th Academy Awards in 2014, DiCaprio’s future Oscar winner was replaced by Matthew McConaughey’s performance in Dallas Buyers Club.