As franchises quickly dominate the moviegoing landscape, traditional movie stars are becoming a thing of the past. But certain actors are talented and popular and captivating enough to be franchise-proof. Leonardo DiCaprio is one of the few bona fide movie stars left in Hollywood, still able to draw superhero-sized crowds to original titles based on his involvement alone.
Great actors can’t shine on their own; they need well-matched co-stars with whom to create a tangible on-screen dynamic. DiCaprio has been paired with such unforgettable scene partners as Jonah Hill and Brad Pitt.
Jack Nicholson In The Departed
Martin Scorsese’s The Departed is a riveting cat-and-mouse thriller starring DiCaprio and Matt Damon as an undercover detective infiltrating the Irish Mob and a crooked cop leaking information to the Irish Mob, respectively, as they try to figure out each other’s identities.
Despite being the leads of the movie, DiCaprio and Damon don’t share a lot of scenes together. DiCaprio’s most memorable Departed co-star is Jack Nicholson as crime boss Frank Costello. Based on Whitey Bulger, Costello is a ruthless gangster who turns out to be colluding with the FBI. As an undercover cop who infiltrates his syndicate, DiCaprio creates a fascinating on-screen dynamic with Nicholson.
Robert De Niro In This Boy’s Life
DiCaprio is about to reunite with Robert De Niro in Scorsese’s upcoming western Killers of the Flower Moon, but their first collaboration hit screens decades ago. This Boy’s Life stars a young DiCaprio as Tobias Wolff opposite De Niro as his abusive stepfather Dwight Hansen. Ellen Barkin plays Toby’s mother, Caroline.
This movie caught critics’ attention as a brutally honest portrayal of a violent household, and a large part of that is DiCaprio and De Niro committing to their characters’ burning mutual hatred.
Cate Blanchett In The Aviator
One of DiCaprio’s most memorable roles in a Scorsese movie is entrepreneur Howard Hughes in the biopic The Aviator. The scope of the movie covers most of Hughes’ life and a bunch of his closest relationships.
The most compelling relationship in the movie is Hughes’ fleeting romance with Hollywood starlet Katharine Hepburn. Cate Blanchett gives a spot-on performance as Hepburn and shares such palpable chemistry with DiCaprio that it was reprised recently in Netflix’s Don’t Look Up.
Kate Winslet In Titanic
James Cameron’s Titanic took one of the greatest tragedies of the 21st century and turned it into the biggest blockbuster of all time. DiCaprio was perfectly paired with Kate Winslet for Cameron’s retelling of Romeo and Juliet aboard a doomed ocean liner.
DiCaprio and Winslet shared strong enough romantic chemistry to sell billions of dollars’ worth of tickets. The duo later reunited for a brilliantly acted adaptation of Revolutionary Road.
Samuel L. Jackson In Django Unchained
In Quentin Tarantino’s blood-drenched spaghetti western Django Unchained, DiCaprio’s vicious villain Calvin Candie shares a wildly unconventional father-son dynamic with Samuel L. Jackson’s secondary antagonist, Stephen.
DiCaprio plays a sadistic plantation owner and Jackson plays the house slave who helped to raise him. Candie is one of the most hateable villains in movie history, but his relationship with Stephen oddly humanizes him.
Daniel Day-Lewis In Gangs Of New York
Scorsese’s ambitious origin story for America, Gangs of New York, is framed through a classic revenge tale. DiCaprio plays a street-smart kid who plots to avenge the murder of his father by Bill the Butcher.
Bill is played unforgettably by Daniel Day-Lewis. DiCaprio does a fine job of holding his own opposite Day-Lewis, who’s widely regarded to be one of the greatest actors in the world.
Jennifer Lawrence In Don’t Look Up
Adam McKay’s Don’t Look Up, a satirical allegory for climate change about a comet heading to Earth, has one of the starriest casts in recent memory, featuring such stars as Meryl Streep, Jonah Hill, Timothée Chalamet, and Tyler Perry.
The cast is led by a perfectly matched Leonardo DiCaprio and Jennifer Lawrence. DiCaprio plays a nervous, neurotic type who can’t string a sentence together on the air or get to the point in the Oval Office. Lawrence offers a hilarious counterpoint as his much more confident and outspoken protégé.
Tom Hanks In Catch Me If You Can
Steven Spielberg’s hilarious cat-and-mouse crime caper Catch Me If You Can stars DiCaprio as teenage con artist Frank Abagnale, Jr. and Tom Hanks as the by-the-book lawman desperately trying to catch him.
The movie wrings its biggest laughs out of the hysterical dichotomy of a mischievous kid staying one step ahead of a highly trained FBI agent. DiCaprio plays the cunning charmer as effectively as Hanks contrasts it with egg-on-his-face embarrassment.
Jonah Hill In The Wolf Of Wall Street
According to Variety, Jonah Hill took a massive pay cut to work with Scorsese on The Wolf of Wall Street. Hill fit the pitch-black comedic tone of the movie like a glove and made a hilarious foil for DiCaprio’s all-in portrayal of Jordan Belfort.
DiCaprio and Hill share extraordinarily convincing chemistry as best friends bonding over excess and depravity. The Quaaludes scene in particular is a masterclass of physical comedy.
Brad Pitt In Once Upon A Time In Hollywood
DiCaprio reunited with Tarantino to star in Once Upon a Time in Hollywood opposite fellow A-lister Brad Pitt as a fading western star and his out-of-work stunt double, respectively. This made for an interesting dynamic through which to explore the fall of Old Hollywood. DiCaprio and Pitt, united on the big screen for the first time, were an A-lister pairing on par with Paul Newman and Robert Redford in Butch Cassidy and the Sundance Kid.
The two shared impeccable chemistry as an insecure wreck and the laidback friend who’s constantly having to calm him down: “You’re Rick f**kin’ Dalton, don’t you forget it.”