Leonardo DiCaprio and Martin Scorsese are teaming up again for another historical biopic, this time the life of former U.S. president Teddy Roosevelt. The Oscar-winning collaborators are no strangers to exploring true stories together, and currently have two other projects in development, including an adaptation of “Devil in the White City,” in which DiCaprio will play America’s first serial killer, H.H. Holmes.
In light of the latest DiCaprio-Scorsese collaboration, here are 10 times DiCaprio has played a historical figure, from early gems like “The Basketball Diaries” to crowd-pleasers like “Catch Me If You Can.”
One of Leonardo DiCaprio’s earliest roles was “This Boy’s Life,” where he shared the screen with Robert De Niro. The film is based on the memoirs of Tobias Wolff, and details the relationship between Wolff (DiCaprio) and his abusive stepfather (De Niro) during the 1950s.
In 1995, DiCaprio starred in “The Basketball Diaries,” an adaptation of Jim Carroll’s memoir about his descent from high-school basketball star into a runaway and heroin addict.
DiCaprio took on the role of young, wild French poet Arthur Rimbaud in “Total Eclipse.” Rimbaud engages in a forbidden romance with his mentor Paul Verlaine (David Thewlis) until a tragedy forces them apart.
After the success of “Titanic,” DiCaprio played dual roles in “The Man in the Iron Mask,” as hedonistic King Louis XIV of France and the king’s secret twin brother, who is imprisoned to prevent his legitimate claim to the throne.
DiCaprio teamed up with Steven Spielberg to tell the real-life story of Frank Abagnale Jr., who successfully forged checks while posing as a pilot, a doctor, and a lawyer in the 1960s. The film was highly successful and earned DiCaprio his third Golden Globe nomination.
True, DiCaprio’s character Amsterdam Vallon wasn’t a real person, but Martin Scorsese’s 2002 film is based on a nonfiction account of the “Five Points” neighborhood in New York City. The names of actual 19th-century gangs were used, the draft riots really occured, and the Butcher (Daniel Day-Lewis) was based on a real-life gang leader, Bill Poole.
Scorsese and DiCaprio teamed up yet again for “The Aviator,” a biopic about Howard Hughes’ life and career from the late 1920s to the mid 1940s. DiCaprio won a Golden Globe for the role, and received his second Academy Award nomination.
J. Edgar Hoover’s nearly 50-year career in the F.B.I. gets the biopic treatment in this Clint Eastwood film. DiCaprio ages in front of the camera, exploring Hoover’s career, his most famous cases, and his notorious penchant for uncovering dirty secrets — all while having several of his own.
Scorsese and DiCaprio teamed up for another biopic with “The Wolf of Wall Street,” which details the debauched rise and fall of Jordan Belfort, a stock-broker steeped in excesses of drugs, sex, alcohol, and money.
DiCaprio finally won an Oscar for his portrayal of real-life frontiersman Hugh Glass, who is severely attacked by a bear and left to die. DiCaprio pushed himself to extremes, portaying Glass’ remarkable will to survive in the most inhospitable environments, until he finally returns home intent on revenge.
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