Leonardo DiCaprio turned 40 on Wednesday, and already he’s had a career more glittering and diverse than most enjoy in a lifetime. After appearing in commercials and featuring as a homeless boy in the sitcom “Growing Pains,” Leo made his first splash as an actor at age 19, playing a mentally impaired boy in “What’s Eating Gilbert Grape.” The role earned him a Best Supporting Actor nod, but for a while it looked like Leo, wooing millions of girls around the world as Jack Dawson and Romeo, wouldn’t graduate from the realm of teenage idols into a serious actor. But just as he went from child star to heartthrob, Leo ground out a career for himself, becoming a well-respected thespian through stellar performances in movies like “Gangs of New York” and “Catch Me If You Can.” He has been nominated for the acting Oscar four times. No joy so far, but with decades still before him, Leo is sure to grab that golden statuette sooner rather than later.
– Elaine
“Titanic” (1997)
Cast: Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates, Frances Fisher, Gloria Stuart, Bill Paxton, Bernard Hill, Victor Garber, David Warner, Ewan Stewart, Ioan Gruffudd
Available to rent or purchase from Amazon Instant and iTunes, streaming on Netflix
For better or worse, “Titanic” will remain one of Leo’s defining roles, and while it’s easy to deride him in his heartthrob days, golden hair and green eyes shimmering while sketching nude Kate Winslet, he was already showing glimpses of the talent he would become. “Titanic” is all about spectacle, but Leo gives the movie a levity and a joie de vivre that prevents it from taking itself too seriously. Like the romantic artist-drifter he plays, Leo seems to be enjoying every moment of the ship’s fateful voyage, and his energy and boyish charm play off Winslet’s gumption and moxie to give us one of cinema’s enduring romances.
– Elaine
“Catch Me If You Can” (2002)
Cast: Leonardo DiCaprio, Tom Hanks, Christopher Walken, Martin Sheen, Nathalie Baye, Amy Adams, James Brolin, Brian Howe
Available to rent or purchase on iTunes and Amazon Instant, on disc from Netflix
In retrospect, Spielberg’s charming dramedy seems something of a turning point for DiCaprio – part of his transformation from teen idol to a respected and adventurous leading man. As real-life con man Frank Abagnale, Jr., DiCaprio uses his boyish good looks and enthusiasm in service of schemes only a teenager could dream up, faking his way through an adult world he can barely understand but certainly knows how to enjoy. Doctor, lawyer, detective, airline pilot; Frank takes everything he’s absorbed from pop culture, adds in a smattering of bullshit and powers through it all. The how-did-he-do-that con scenes (accompanied by John Williams’ jaunty, jazzy score) are the most fun, but Spielberg’s film has a real heart in the scenes between DiCaprio and Hanks, as the dogged federal agent pursuing, and, bizarrely, befriending Frank at the same time.
– Ethan
“The Great Gatsby” (2013)
Cast: Tobey Maguire, Leonardo DiCaprio, Carey Mulligan, Joel Edgerton, Elizabeth Debicki, Jason Clarke, Isla Fisher
Available to purchase on Amazon Instant and iTunes, on disc from Netflix
Baz Luhrmann’s addled adaptation of F. Scott Fitzgerald’s class novel at least gets points for trying, I suppose – for every horrendous passage of Nick Carraway’s voice-over narration or over-saturated Baz-infused rumpus there’s a counterpoint of fine character work by the director’s spot-on cast. And leading the pack is DiCaprio, who nails everything about the grasping, idealistic, tragic Jay Gatsby: the false bravado glued together by a sincere charm and deep-seeded desperation, the juvenile worldview packaged inside a street-smart operator. Everything about DiCaprio’s performance screams superficiality (his entrance, with fireworks blazing and Gershwin blaring, is one of the finest moments of Luhrmann’s career), from his gleaming smile to forced accent – until the genuine, lovestruck Jay Gatz pokes through, in tender and comic moments. The scene where he has tea with Nick and Daisy in Nick’s cottage is a delight – a superb bit of physical comedy from DiCaprio mixed with a real, endearing romantic yearning.
– Ethan
The Best Films of Our Lives 