The Aviator (2004)

From author Tobias Wolff in This Boy’s Life (1993) to murderer Ernest Burkhart in Killers of the Flower Moon (2023), Leonardo DiCaprio is no stranger to playing real life people on screen. Throughout his successful career, he’s portrayed writer Jim Carroll in The Basketball Diaries (1995); poet Arthur Rimbaud in Total Eclipse (1995); sovereign King Louis XIV in The Man in the Iron Mask (1998); con-artist Frank Abagnale Jr. in Catch Me If You Can (2002); FBI director J. Edgar Hoover in J. Edgar (2011); stockbroker Jordan Belfort in The Wolf of Wall Street (2013); frontiersman Hugh Glass in The Revenant (2015); and even a comical himself in The Audition (2015). In between these impressive credits, Leo took on the part of Howard Hughes in The Aviator (2004). Under the direction of Martin Scorsese, this big screen biopic is based on Charles Higham’s non-fiction book “Howard Hughes: The Secret Life” (1993). The period piece begins in 1913 and goes through 1947, documenting Howard’s input on aviation, politics and motion pictures. While in Hollywood, he rubs elbows (and more) with Ava Gardner (Kate Beckinsale), Errol Flynn (Jude Law), Jean Harlow (Gwen Stefani), Louis B. Mayer (Stanley DeSantis), and Katharine Hepburn (Cate Blanchett in her first Oscar-winning turn). While stepping into the role of the famed philanthropist, investor, business tycoon, movie producer, aerospace engineer and pilot, Leo had to wear many hats. Yet Mr. Man prefers when Mr. DiCaprio wears nothing at all. Luckily, the star bares his chest and buns. What a T&A-lister!