Spoiler Alert: Critters 3 isn’t on the list, but you should watch it just for shiggles.
This Boy’s Life (1993)
The role as Toby was Leo’s first leading role. The movie also stars Ellen Barkin and Robert De Niro, who play a pushover house wife and abusive stepdad respectively. Along with Who’s Eating Gilbert Grape, This Boy’s Life gave us a glimpse of the complex actor to come.
Romeo and Juliet (1996)
How can I truly describe the importance of a Baz Luhrmann film that single-handedly destroyed Shakespeare’s iconic words all while making Gen-Xer hearts flutter with delight? The chemistry between Leo and Claire Danes is undeniable from their first glance through that brightly colored fish tank. Leo pulls out all his best emo moves as Romeo and I loved every minute. I DEFY YOU, STARS!
Revolutionary Road (2008)
Leo’s best roles are often supremely unhappy ones. Boy’s gotta killer scowl and pout. Revolutionary Road is the cautionary tale of what might have happened to Jack and Rose if she shared the floating piece of debris, they both live and settle into a nice life trapped in suburbia hell. It’s hard to watch and beautiful all at the same time.
The Departed (2006)
Scorsese finally won his long overdue Oscar with his gritty crime drama, starring Leo as an undercover cop infiltrating a Boston gang. Ironically, Leo’s toughest competition this award season, Matt Damon, is also in this flick. Both give stellar performances, but I have to tip my little fangirl heart towards Leo with the fantastically awkward love scene with his ex-therapist/dating another guy/friend who’s a girl, Madolyn. Leo’s “vulnerability” freaks everybody out, Madz. We get you, girl.
James Cameron’s disaster story became a record-breaking, Oscar winning, all-around pop-culture phenomenon. What it really comes down to, though, is the love between Jack and Rose. Rich girl falls for poor boy against the wishes of her mother is the tale as old as time and this version simply does not disappoint. Leo and Kate Winslet were gorgeous as the star-crossed lovers … and both actors became household names after the film was released.
If there is a woman in existence that hasn’t thought about Jack Dawson drawing her like one of his French girls … they’re dead on the inside.
The Great Gatsby, Blood Diamond, Inception, The Wolf of Wall Street, Gangs of New York, Catch Me If You Can … I could, literally, list his whole IMDB page and they would all be great movies. Except for The Man In The Iron Mask and Critters 3.
Well, maybe The Man In The Iron Mask, because he plays twins and we’ve all thought about that at least once … ammarite, ladies?