“The Basketball Diaries,” one of the A-lister’s early films, turns 25 on Tuesday and finds DiCaprio – who at the time had a stint on TV’s “Growing Pains” and an Academy Award nomination on his resume – playing a high school basketball player with a poet’s heart and addiction issues. It’s not his greatest film, though it’s intriguing to look at the now-45-year-old actor’s whole filmography, from his many collaborations with director Martin Scorsese to that time DiCaprio and Kate Winslet boarded a sinking ship to megastardom.
Here’s how “Basketball Diaries” stacks up with the best and worst of DiCaprio’s career. (Not included is the 2001 black-and-white indie drama “Don’s Plum” that DiCaprio and co-star Tobey Maguire sued to keep from being released in the USA.)
28. ‘Critters 3’ (1991)
Everybody’s got to start somewhere, and DiCaprio’s Hollywood debut was in a straight-to-video horror travesty where the then-17-year-old thespian dealt with a whole bunch of furry aliens with nasty dispositions invading an apartment complex.
27. ‘Poison Ivy’ (1992)
DiCaprio is only in the indie erotic thriller for a few seconds (he’s credited as “Guy”), though the film itself earned some cult cache with Drew Barrymore starring as a teen femme fatale and Sara Gilbert as the private-school girl she befriends.
26. ‘The Beach’ (2000)
Danny Boyle’s drama at least offers luscious cinematography and DiCaprio in full post-“Titanic” heartthrob mode. However, the adaptation of Alex Garland’s acclaimed novel is a mess, with DiCaprio starring as an American seeking adventure in Thailand and finding sex, sharks and sandy soap-opera nonsense in a secret paradise.
25. ‘Total Eclipse’ (1995)
For completists of DiCaprio and director Agnieszka Holland’s filmographies only, the drama explores the scandalous world of 19th-century French poetry with uninhibited teenager Arthur Rimbaud (DiCaprio) seducing his older (and married) contemporary, Paul Verlaine (David Thewlis).
24. ‘The Man in the Iron Mask’ (1998)
DiCaprio has dual roles – breaking bad as King Louis XIV but also wearing unfortunate headgear as the title character – in the forgettable action flick that doubles as a Three Musketeers movie with Jeremy Irons, Gabriel Byrne, John Malkovich and Gerard Depardieu as the aging, sword-swinging heroes.
23. ‘Celebrity’ (1998)
The only movie where DiCaprio shared the same big screen with Donald Trump, who played himself in Woody Allen’s star-filled black-and-white ensemble comedy. Kenneth Branagh takes the lead as a former novelist who dives into the world of entertainment journalism, and DiCaprio is one of his subjects, a wild-child A-lister.
22. ‘The Great Gatsby’ (2013)
“Gatsby” the movie wasn’t that great. DiCaprio at least gave some needed sparkle and an old-school movie-star feel to the uber-wealthy and enigmatic Jay Gatsby in Baz Luhrmann’s ostentatious adaptation of F. Scott Fitzgerald’s classic novel. And, hey, it also gave us a pretty awesome “Leo cheers” GIF.
21. ‘The Basketball Diaries’ (1995)
Alongside a very crazy Mark Wahlberg, DiCaprio is a prep-school hoopster, part-time juvenile delinquent and up-and-coming writer in this melodrama that veers from teenage shenanigans that tick off the closeted coach (Bruno Kirby) to heroin addiction that threatens the youngsters’ futures.
20. ‘Body of Lies’ (2008)
Ridley Scott’s action thriller brought together DiCaprio, here playing a CIA officer tracking an international terrorist in the Middle East, and Russell Crowe as the agency boss who might not be totally on the level. Even with that level of talent, it’s a spy flick that’s way better on paper than in execution.
19. ‘Blood Diamond’ (2006)
The action-packed political thriller finds DiCaprio as a South African mercenary and smuggler who, while searching for a valuable diamond in Sierra Leone, gets embroiled in the civil war and forms a partnership with an American journalist (Jennifer Connelly) and a man (Djimon Hounsou) searching for his son.
18. ‘Marvin’s Room’ (1996)
A young DiCaprio nabbed one heck of a Hollywood mom, Meryl Streep, in this drama about a dysfunctional family revolving around two sisters (Streep and Diane Keaton) who reconnect when one of them is diagnosed with leukemia. DiCaprio co-stars as a former mental patient who forms a close bond with his ailing aunt.
17. ‘This Boy’s Life’ (1993)
Taking on Robert De Niro would be intimidating any time in an actor’s career, and DiCaprio drew the legend in his first major film role. But DiCaprio holds his own as a troubled teenager coming of age in the 1950s opposite De Niro as the kid’s abusive new stepfather.
16. ‘Revolutionary Road’ (2008)
While DiCaprio and Winslet’s second go-round together wasn’t a “Titanic” box-office success, Sam Mendes’ retro relationship drama was another acting showcase for the pair as a seemingly perfect married couple becomes a suburban cautionary tale when the lovers are torn apart by infidelity, resentment and apathy.
15. ‘The Quick and the Dead’ (1995)
Sharon Stone moseys into the Old West town of Redemption as a gunfighter looking to settle a score with the ruthless outlaw (Gene Hackman) who runs the place. Famous faces abound in Sam Raimi’s shoot-out setting, including Russell Crowe as a criminal-turned-preacher and DiCaprio as a baby-faced wannabe who believes the big bad is his dad.
14. ‘What’s Eating Gilbert Grape’ (1993)
DiCaprio earned his first Oscar nod (for supporting actor) playing the mentally impaired, troublemaking younger brother of Johnny Depp’s extremely caring title character. It’s definitely a sentimental and quirky tale but one with heart that offers an early peek at the kind of nuance DiCaprio would pull off later in his career,
13. ‘Django Unchained’ (2012)
Quentin Tarantino’s violent spaghetti-Western-tinged revenge flick centers very much on Jamie Foxx’s title bounty hunter, a former slave seeking his wife, but as the deliciously evil Mississippi plantation owner Calvin Candie, DiCaprio is an unscrupulous, scenery-chewing monster you absolutely love to hate. Get the Entertainment newsletter in your inbox.
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12. ‘J. Edgar’ (2011)
DiCaprio turned out to be an inspired choice for Clint Eastwood’s biopic, playing J. Edgar Hoover over several decades, from his beginnings in the Justice Department to running the FBI. The movie explores the complicated personal and professional lives of the hard-nosed, not-always-heroic lawman played with passion by DiCaprio.
11. ‘Shutter Island’ (2010)
Since “Critters,” DiCaprio hasn’t done a bunch of horror. This bit of 1950s psychological freakiness by Scorsese probably counts, with DiCaprio and Mark Ruffalo as a pair of U.S. marshals investigating the disappearance of a mental patient at a Boston Harbor asylum and finding a host of mind-twisting terrors while there.
10. ‘Romeo + Juliet’ (1996)
This is how you got teenagers to pay attention to Shakespeare in the mid-1990s: A pre-“Titanic” DiCaprio starring as Romeo, Claire Danes (hot off “My So-Called Life”) as Juliet, and Baz Luhrmann putting an iconoclastic spin on the tragic love story, modernizing it to Verona Beach and filling it with sun-drenched California gang members.
9. ‘Catch Me If You Can’ (2002)
Steven Spielberg’s true-life 1960s-set cat-and-mouse crime story paired DiCaprio, playing a teenage grifter who posed as everything from a Pan American pilot to a Southern doctor, with Tom Hanks co-starring as the FBI man on the hunt. It’s not only stylish as heck but also features a spectacularly jazzy John Williams score.
8. ‘Gangs of New York’ (2002)
The first collaboration between DiCaprio and Scorsese is an expansive 19th-century New York City story with bruising brutality. The bloody history lesson stars DiCaprio as Amsterdam Vallon, a young man looking to avenge the death of his Irish immigrant father (Liam Neeson) by destroying his killer, the inimitable Bill the Butcher (Daniel Day-Lewis), from the inside of his xenophobic gang.
7. ‘Titanic’ (1997)
We would’ve made room for you on the raft, Leo. DiCaprio was already a star, but the epic sinking-ship disaster blockbuster propelled him into supernova status. Seriously, who doesn’t weep as ghost Jack waits, smiling with hand outstretched, for Kate Winslet’s Rose to take the boat to heaven?
6. ‘Once Upon a Time in Hollywood’ (2019)
Although DiCaprio’s career is anything but washed up, he fantastically plays down-on-his-luck, insecure ‘60s actor Rick Dalton opposite Brad Pitt’s steely stunt double Cliff Booth. Tarantino’s film is a love letter to old Hollywood and a tale of career redemption that ends in enjoyably fiery fashion.
5. ‘The Revenant’ (2015)
Did DiCaprio finally win an Oscar pretty much for getting mauled by a CGI bear and living? His gripping portrayal in the survival drama of Hugh Glass, a frontiersman betrayed by his fellow man, left for dead and then avenging like a champ, was impressive stuff, and the bear was just the cherry on the sundae.
4. ‘The Wolf of Wall Street’ (2013)
Scorsese’s comedic crime drama – and cautionary tale about greed – cast DiCaprio as notorious real-life stockbroker Jordan Belfort. It’s definitely not for the easily offended, considering the rampant swearing, sex and all-around immorality, yet it’s a ton of fun watching DiCaprio navigate the morass, including crawling to a Lamborghini while extremely high on Quaaludes.
3. ‘Inception’ (2010)
Christopher Nolan’s sci-fi action film is a twisty mind-bender, though DiCaprio is a grounding aspect. His Cobb is a dream thief who procures valuable secrets from various marks in the game of corporate espionage, and there’s a deep backstory with DiCaprio’s character involving family that adds depth to the whiz-bang visuals.
2. ‘The Departed’ (2006)
Part of an all-star ensemble (Jack Nicholson, Matt Damon, Alec Baldwin) in Scorsese’s Oscar-winning gangster flick (a remake of the Hong Kong film “Infernal Affairs”), DiCaprio plays a Boston cop assigned to go undercover and infiltrate the inner workings of a Mob boss (Nicholson), but he’s not the only mole in a criminal masterwork filled with them.
1. ‘The Aviator’ (2004)
The Scorsese/DiCaprio duo has given us a bunch of great flicks. The best, however, is the astounding biopic with DiCaprio as media mogul Howard Hughes. The actor plays the infamous icon impressively through his descent into madness, from Hollywood filmmaker and airborne bon vivant to eccentric OCD recluse later in life.