In an attempt to shed his image of a romantic hero, DiCaprio sought roles in other genres, including the 2002 crime dramas Catch Me If You Can and Gangs of New York; the latter marked the first of his many successful collaborations with director Martin Scorsese.

[29] By the early 1990s, DiCaprio began acting regularly on television, starting with a role in the pilot of The Outsiders (1990) and one episode of the soap opera Santa Barbara (1990), in which he played a teenage alcoholic.

[33][34] DiCaprio made his film debut in 1991 as the stepson of an unscrupulous landlord in the low-budget horror sequel Critters 3—a part he later described as "your average, no-depth, standard kid with blond hair".

Adapted from the memoir by Tobias Wolff, the film focuses on the relationship between a rebellious teenager, Toby (DiCaprio), and his mother (Ellen Barkin) and abusive stepfather (De Niro).

[48][49] "The film's real show-stopping turn comes from Mr. DiCaprio," wrote New York Times critic Janet Maslin, "who makes Arnie's many tics so startling and vivid that at first he is difficult to watch.

[59] DiCaprio next starred opposite Claire Danes in Baz Luhrmann's Romeo + Juliet (1996), an abridged modernization of William Shakespeare's romantic tragedy, which retained the original Shakespearean dialogue.

[64] He then portrayed a young man who has been committed to a mental asylum in Marvin's Room (1996), a family drama about two estranged sisters, played by Meryl Streep and Diane Keaton, who are reunited through tragedy.

[65] Lisa Schwarzbaum of Entertainment Weekly praised "the deeply gifted DiCaprio" for holding his own against veteran actresses Keaton and Streep, describing the three as "full-bodied and so powerfully affecting that you're carried along on the pleasure of being in the presence of their extraordinary talent".

"[79] In his 2015 Rolling Stone article, Ebiri called the role DiCaprio's best, writing that he and Winslet "infuse their earnest back-and-forth with so much genuine emotion that it's hard not to get swept up in their doomed love affair.

In Scorsese's The Departed, DiCaprio played the role of Billy Costigan, a state trooper working undercover in the Irish Mob in Boston, someone he characterizes as being in a "constant 24-hour panic attack".

[123] Despite DiCaprio's leading role in The Departed, the film's distributor Warner Bros. Pictures submitted his performance for a Best Supporting Actor nomination at the AMPAS to avoid internal conflict with his part in Blood Diamond.

[129] Claudia Puig of the USA Today approvingly highlighted DiCaprio's transition from a boy to a man on screen,[130] and Ann Hornaday of The Washington Post similarly noted his growth as an actor since The Departed.

[125] In 2007, DiCaprio produced the comedy drama Gardener of Eden, which according to The Hollywood Reporter's Frank Scheck "lack[ed] the necessary dramatic urgency or black humor to connect with audiences".

[140] Peter Travers liked DiCaprio's pairing with Winslet and his multi-layered portrayal of an overwhelmed character,[141] and Marshall Sella of GQ called it the "most mature and memorable performance of his lifetime".

[103][155] To star in this film, DiCaprio agreed to a pay cut from his $20 million fee and opted for a share in first-dollar gross points, which entitled him to a percentage of the cinema ticket sales.

[158][159] Roger Ebert praised DiCaprio's ability to bring depth and nuance to the character, suggesting that his performance conveyed aspects of Hoover's personality that were possibly even unknown to the man himself.

[212] A writer for Business Insider called it one of the best performances of DiCaprio's career,[213] and Ian Sandwell of Digital Spy particularly liked the duo's chemistry, believing their scenes together to be some of the film's strongest parts.

As a frequent supporter of environmentalism, DiCaprio said he has often looked to star in and make films tackling issues related to it, something he found hard due to people's inability to listen.

[228] Initially signed for the heroic part of FBI agent Thomas Bruce White Sr., DiCaprio insisted on playing the morally complex role of murderer Ernest Burkhart, leading to extensive script rewrites.

[229][230] Declaring it the best performance of DiCaprio's career, IndieWire's David Ehrlich wrote that "his nuanced and uncompromising turn as the cretinous Ernest Burkhart mines new wonders from the actor's long-standing lack of vanity".

[38][234] In an infamous article published by New York Magazine in 1998, journalist Nancy Jo Sales criticized the group as men whose pursuit was to "chase girls, pick fights and not tip the waitress".

"[9] Steven Spielberg, who directed him in Catch Me If You Can, defended DiCaprio's reputation as a "party boy", believing it is a common behavior for young people and describing him as a family-oriented person during the film's production.

[20][244] According to Caryn James, DiCaprio is unafraid of working with established directors on unconventional projects; taking such risks has led him to star in failed films like The Beach (2000),[51] but also his successful collaborations with Martin Scorsese.

Club considers the duo's collaborations—which earned them the 2013 National Board of Review (Spotlight Award)[248]—to be career-defining moments for both of them and as vital as Scorsese's acclaimed collaborations with Robert De Niro.

[249] Author Michael K. Hammond wrote that DiCaprio built his star reputation by demonstrating his acting ability, and praised him for "revealing a character while concealing the actor" and "disappearing into [his] roles".

[302] In October 2024, DiCaprio formally endorsed Democratic nominee Kamala Harris for president, citing her policies on climate change mitigation, while criticizing her Republican opponent Donald Trump.

[304] In May 2009, DiCaprio joined Kate Winslet, director James Cameron and Canadian singer Celine Dion, in a campaign to raise money to financially support the fees of the nursing home where Millvina Dean, a survivor of the RMS Titanic, was residing.

[328] In 2009, he bought an island, Blackadore Caye, off mainland Belize—on which he is set to open an environment-friendly resort[329][330]—and in 2014, he purchased the original Dinah Shore residence designed by architect Donald Wexler in Palm Springs, California.

[333] In 2017, when The Wolf of Wall Street producer Red Granite Pictures was involved in the 1Malaysia Development Berhad scandal, DiCaprio turned over the gifts he received from business associates at the production company, including from fugitive businessman Jho Low, to the US government.

[336] According to the online portal Box Office Mojo and the review aggregate site Rotten Tomatoes, DiCaprio's most critically and commercially successful films include What's Eating Gilbert Grape (1993), Romeo + Juliet (1996), Titanic (1997), Catch Me If You Can (2002), Gangs of New York (2002), The Aviator (2004), The Departed (2006), Blood Diamond (2006), Shutter Island (2010), Inception (2010), Django Unchained (2012), The Great Gatsby (2013), The Wolf of Wall Street (2013), The Revenant (2015), Once Upon a Time in Hollywood (2019), Don't Look Up (2021), and Killers of the Flower Moon (2023).