Leonardo DiCaprio recently starred in Netflix's Killers of the Flower Moon.
DiCaprio began acting at the age of 14, transitioning from commercials for Apple Jacks and Mattel to appearances on television shows like Roseanne and Growing Pains. After a breakout role in the film This Boy's Life with Robert De Niro and What's Eating Gilbert Grape with Johnny Depp, he evolved seamlessly from a bona fide child star to a teen heartthrob to a dramatic adult actor with a vast and varied filmography, starring in multiple high-profile projects with a vast array of collaborators. Seven Oscar nominations and one win later, DiCaprio has cemented himself as a movie star dedicated to taking on bold, diverse, and challenging roles, leading to some of the best Hollywood has to offer.
DiCaprio has taken on many roles since his arrival in Hollywood, including actor, producer, and adamant environmentalist. His production company, Appian Way Productions, has produced a number of his own films, as well as documentaries, features, and TV projects, including Orphan, Out of the Furnace, Richard Jewell, The 11th Hour, Ice on Fire, and more. DiCaprio has run the gamut in his busy career, collaborating with some of the most prominent filmmakers working today, from Scorsese to Spielberg to Nolan to Tarantino. Indeed, his resume could almost double as a time capsule of the last 30 years of American cinema.
Leonardo DiCaprio has starred in 29 films so far. These vary from his early b-movie entries like Critters to his high-profile, critically acclaimed roles, like Titanic or Shutter Island. Here's a look back at all of his films, ranked from worst to best.
29. Critters 3
Leo fans could probably debate for a year about his greatest performance and never make one mention of his 1992 film debut in Critters 3. A critically-derided Gremlins wannabe, its bare-bones plot concerns a race of hairy aliens infesting an apartment building. Leo plays the landlord's son, Josh, and while he survives his encounter with the titular critters, he did not return for the intergalactic-set fourth entry.
28. The Man in the Iron Mask
The remake The Man in the Iron Mask is another weaker Leonardo DiCaprio movie. Riding the success of 1997's monster hit Titanic, this loose adaptation of Alexandre Dumas' second sequel to The Three Musketeers actually performed quite well at the box office. Alas, audiences more than a decade removed from "Leo Mania" may wonder what all the fuss was about; this is ultimately a pretty low-grade, cheesy effort, wasting a cast that includes legends like Jeremy Irons, John Malkovich, Gerard Depardieu, and Gabriel Byrne. Leo himself plays the dual role of King Louis XIV and his imprisoned twin brother, making little impact with either. Directed by Braveheart's Randall Wallace, the expectation was for something more polished, but the film struggles to find that level of quality.
27. Total Eclipse
Based on the real-life love affair between 19th-century poets Paul Verlaine and Arthur Rimbaud, this erotic drama was a box office bomb owing mostly to the controversy of a series of fairly-explicit sex scenes between its two actors, Leonardo DiCaprio and David Thewlis. While that sounds groundbreaking in a pre-Brokeback Mountain and Call Me By Your Name age, the resulting film is made almost unwatchable due to the obnoxiousness of its lead characters, who are rendered here as two of the most snobbish, egotistical, and selfish people to ever fall in love in a movie.
26. The Basketball Diaries
The Basketball Diaries tells the story of Jim Carroll, a gifted high school basketball player who falls prey to drug addiction, and while it's based on Carroll's autobiographical novel by the same name, it too often comes across as disingenuous, overwrought, and cliche. Brimming with over-the-top performances and copious montages of basketball and drug use, it's a miserable descent into the depths of addiction that's only really worth watching for Leo's performance, which gives a sense of the big but committed swings he'd continue to make as his career progressed.
25. J. Edgar
The idea of Clint Eastwood tackling a DiCaprio-led biopic about the legendarily controversial director of the FBI may seem ripe with potential. Alas, the resulting film tries too hard to have it both ways, as both a full-blown monster movie about an American villain and as a fair and balanced story about a man whose sexual repression led him to wage war on the marginalized people of his own country. Floating in the midst of this wishy-washy tone is DiCaprio's performance, which is plenty capable but too often at the mercy of the muddled, ultimately confusing film around him, not to mention the pounds of poorly-executed old-age makeup he's buried under.
24. Body of Lies
The 2000s were understandably awash with action thrillers confronting terrorism. Casting Leonardo DiCaprio and Russell Crowe certainly goes a long way to separate Body of Lies from the rest of the pack, but unfortunately little else does. Ridley Scott's direction is tense and polished, but there's something disappointingly workmanlike about the way it hits its familiar beats and then gets out of dodge. Even with a script by The Departed's William Monahan, Body of Lies never reaches the heights it could have, given the talent behind it. For all involved, it's just a fairly forgettable entry.
23. Don's Plum
The most interesting aspect of this black-and-white curiosity is what happened behind the scenes. Shot in 1995 and 1996 and starring a pre-Titanic Leo and pre-Spider-Man Tobey Maguire, the film snagged some buzz when the two actors sued in 2001 to block the film's release. Retrospectively, Don's Plum poses very little threat to their stardom; the two are perfectly fine in this intriguing but meandering slice-of-life talk-fest about a group of young friends who meet at a restaurant every Saturday night. It's worth a look for completionists who can find it; the film is still banned from release in the U.S. and Canada.
22. Don't Look Up
Director Adam McKay's satirical doomsday comedy stars Netflix-exclusive film was a controversial release, taking a shot at everything from politics, news, science, greed, etc., attempting to shine a light on the current cycle of division throughout the world, particularly when faced with a global threat. DiCaprio plays a more low-key, demure character here, but still gets his moment to shine when unleashed, even though it's hardly enough to put the performance in a "best of" category. Ultimately, the heavy-handed satire got people talking, but not about how good the movie was, but rather the divisive issues it brings up.
21. Marvin's Room
The film version of Scott Mherson's play, itself now a staple of community theaters around the country, is a solid piece of work from four-time Tony Award winner Jerry Zaks. It of course doesn't hurt that it stars Meryl Streep, Diane Keaton, and Robert De Niro, but they can only elevate what's ultimately a fairly standard family drama so much. Leo, playing Meryl's son who's been committed to a mental institution for setting her house on fire, holds his own magnificently against these legendary stars, but also seems almost feel him itching to break out of the troubled teen mold for greater pastures.
20. The Quick and the Dead
In 1995, Sam Raimi directed a Sergio Leone-inspired Western wherein Gene Hackman, playing a sadistic mayor, organizes a quick-draw tournament between Leo, Sharon Stone, and Russell Crowe (amongst others). As visually stylish and packed with special effects-driven violence as one might expect from the director of the Evil Dead franchise, The Quick and the Dead doesn't quite stack up to Raimi's best. However, Leonardo DiCaprio fits into its pastiche style well, donning a cocksure swagger as a Billy the Kid-esque cowboy with a deeper connection to the mayor.
