Career Timeline of Leonardo DiCaprio: Major Achievements and Milestones

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Leonardo DiCaprio

From career breakthroughs to professional milestones, explore how Leonardo DiCaprio made an impact.

Leonardo DiCaprio is a highly acclaimed American actor and film producer, celebrated for his roles in biographical and period pieces. His performances have earned him an Academy Award, a British Academy Film Award, and three Golden Globe Awards. DiCaprio is also a commercially successful actor, with his films grossing over $7.2 billion globally as of 2019. He has consistently ranked among the world's highest-paid actors, solidifying his status as a major figure in the film industry.

1929: Release of 'The Man in the Iron Mask'

In 1929, a film titled 'The Man in the Iron Mask' starring Douglas Fairbanks, was released which shared common elements with the 1998 film that Leonardo DiCaprio starred in.

1939: Release of 'The Man in the Iron Mask'

In 1939, a film titled 'The Man in the Iron Mask' was released which shared common elements with the 1998 film that Leonardo DiCaprio starred in.

1961: Publication of Revolutionary Road

In 1961, the novel Revolutionary Road by Richard Yates was published, which served as the basis for the 2008 film starring Leonardo DiCaprio and Kate Winslet.

Revolutionary Road
Revolutionary Road

1974: Release of The Parallax View

In 1974, the political thriller film The Parallax View was released. DiCaprio considered Body of Lies to be a throwback to political features of the 1970s like The Parallax View.

1975: Release of Three Days of the Condor

In 1975, the political thriller film Three Days of the Condor was released. DiCaprio considered Body of Lies to be a throwback to political features of the 1970s like Three Days of the Condor.

1989: Role in The New Lassie

In 1989, Leonardo DiCaprio played the role of Glen in two episodes of the television show The New Lassie.

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1989: Parenthood Film

In 1990 DiCaprio was cast in Parenthood, a series based on the 1989 comedy film of the same name. To prepare for the role of Garry Buckman, a troubled teenager, he analyzed Joaquin Phoenix's performance in the original film.

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1990: Recurring role in Parenthood and The Outsiders

In 1990, Leonardo DiCaprio had a recurring role in the sitcom Parenthood and appeared in the pilot of The Outsiders.

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1990: Acting on Television

In the early 1990s, Leonardo DiCaprio began acting regularly on television, starting with a role in the pilot of The Outsiders in 1990 and one episode of the soap opera Santa Barbara, in which he played a teenage alcoholic. He was also cast in Parenthood, a series based on the 1989 comedy film of the same name.

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1991: Role in Parenthood

From 1990 to 1991, Leonardo DiCaprio played a recurring role in the sitcom Parenthood.

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1991: Film Debut in Critters 3 and Recurring Role in Growing Pains

In 1991, Leonardo DiCaprio made his film debut in Critters 3. Later in 1991, he became a recurring cast member on the sitcom Growing Pains, playing Luke Brower, a homeless boy who is taken in by the show's central family. He also had an uncredited role in one episode of Roseanne in 1991.

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1992: Role in Poison Ivy and This Boy's Life

In 1992, Leonardo DiCaprio had a brief role in the first installment of the Poison Ivy film series. He was also handpicked by Robert De Niro to co-star with him in This Boy's Life.

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1993: Major Film Part in This Boy's Life and Acclaim for What's Eating Gilbert Grape

In 1993, Leonardo DiCaprio had his first major film part as author Tobias Wolff in This Boy's Life and he received critical acclaim and his first Academy Award nomination for playing a developmentally disabled boy in What's Eating Gilbert Grape.

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1993: Role in What's Eating Gilbert Grape

In 1993, Leonardo DiCaprio played the developmentally disabled brother of Johnny Depp's character in What's Eating Gilbert Grape, a comedy-drama about a dysfunctional Iowa family. He earned a National Board of Review Award, as well as nominations for a Golden Globe Award and an Academy Award for Best Supporting Actor for his performance.

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1995: Roles in The Quick and the Dead, The Basketball Diaries, and Total Eclipse

In 1995, Leonardo DiCaprio starred in Sam Raimi's Western The Quick and the Dead, the biopic The Basketball Diaries, and the erotic drama Total Eclipse. For The Quick and the Dead, Sharon Stone paid his salary. Although Total Eclipse failed commercially, it has been included in the catalog of the Warner Archive Collection.

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1996: Publication of The Beach

In 1996, Alex Garland's novel, The Beach, was published. Leonardo DiCaprio would later star in the film adaptation of the book.

1996: International Stardom with Romeo + Juliet

In 1996, Leonardo DiCaprio achieved international stardom with the star-crossed romance film Romeo + Juliet.

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1996: Starring in Romeo + Juliet and Marvin's Room

In 1996, Leonardo DiCaprio starred opposite Claire Danes in Baz Luhrmann's Romeo + Juliet, an abridged modernization of William Shakespeare's romantic tragedy, and portrayed a young man who has been committed to a mental asylum in Marvin's Room.

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1997: Titanic's Release and Stardom

In 1997, Leonardo DiCaprio achieved international stardom with the release of Titanic, which became the highest-grossing film in the world at the time.

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1997: Silver Bear for Best Actor

In 1997, Leonardo DiCaprio earned a Silver Bear for Best Actor at the Berlin International Film Festival for his performance in Romeo + Juliet.

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1997: Starring in Titanic

In 1997, Leonardo DiCaprio starred opposite Kate Winslet in James Cameron's Titanic as members of different social classes who fall in love aboard RMS Titanic during its ill-fated maiden voyage. Titanic became the highest-grossing film at the time, eventually earning more than $2.1 billion in box-office receipts worldwide. The role of Jack Dawson transformed DiCaprio into a superstar.

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1997: International stardom with Titanic

Since Leonardo DiCaprio gained international stardom with the release of "Titanic" in 1997, he has admitted feeling nervous about starring in big-budget studio films.

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1998: DiCaprio stars in Celebrity and The Man in the Iron Mask

In 1998, Leonardo DiCaprio played a role in Woody Allen's "Celebrity", and he also played dual roles in "The Man in the Iron Mask" as King Louis XIV and his twin brother, Philippe. The Man in the Iron Mask received mixed reviews but was a box office success.

1998: DiCaprio cast in American Psycho, then leaves for The Beach

In 1998, Leonardo DiCaprio was initially cast in "American Psycho" but left the project due to disagreements with the director, Oliver Stone. He then took the lead role in "The Beach."

2000: Release of American Psycho

In 2000, American Psycho, the movie DiCaprio was initially cast for, was released.

2000: Starred in The Beach

In 2000, Leonardo DiCaprio starred in "The Beach", which was considered a failed film, but he continued to work with established directors on unconventional projects.

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2000: DiCaprio comments on Titanic phenomenon

In 2000, Leonardo DiCaprio stated that he felt disconnected from the "Titanic" phenomenon and the global recognition of his face. He expressed that he didn't expect to reach that level of popularity again and wouldn't actively pursue it.

2001: Don's Plum premieres at Berlin International Film Festival

In 2001, "Don's Plum" premiered at the Berlin International Film Festival. This movie was blocked from release in the US and Canada due to legal actions by DiCaprio and Tobey Maguire.

2002: Roles in Catch Me If You Can and Gangs of New York

In 2002, Leonardo DiCaprio sought roles in other genres, including the 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.

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2002: DiCaprio stars in Catch Me If You Can

In 2002, Leonardo DiCaprio starred in "Catch Me If You Can", a biopic directed by Steven Spielberg based on the life of Frank Abagnale Jr. The film was critically acclaimed and a box office success.

2002: DiCaprio stars in Gangs of New York

In 2002, Leonardo DiCaprio starred in Martin Scorsese's "Gangs of New York," a historical drama set in the 19th century. His involvement helped secure financing for the project. The film received positive reviews.

2003: Publication of Shutter Island

In 2003, the novel Shutter Island by Dennis Lehane was published, and was later adapted into the 2010 film.

Shutter Island
Shutter Island

2004: Acclaim for The Aviator

In 2004, Leonardo DiCaprio continued to gain acclaim for his performance in the biopic The Aviator.

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2004: DiCaprio founds Appian Way Productions and stars in The Aviator

In 2004, Leonardo DiCaprio founded the production company Appian Way Productions. He also starred in "The Aviator", a biopic of Howard Hughes directed by Martin Scorsese, which he co-produced under Appian Way. The film was a critical and financial success.

2005: Commander of the Order of Arts and Letters

In 2005, Leonardo DiCaprio was named a Commander of the Order of Arts and Letters for his contributions to the arts.

2006: Roles in Blood Diamond and The Departed

In 2006, Leonardo DiCaprio gained acclaim for his performances in the political thriller Blood Diamond and the crime drama The Departed.

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2006: DiCaprio stars in The Departed and Blood Diamond

In 2006, Leonardo DiCaprio starred in "The Departed" and "Blood Diamond". In The Departed, he played an undercover state trooper in the Irish Mob. "The Departed" became DiCaprio and Scorsese's highest-grossing collaboration to that point. 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.

2007: DiCaprio and Scorsese become interested in Shutter Island

In 2007, Leonardo DiCaprio and Martin Scorsese became interested in the project Shutter Island, a film based on the 2003 novel of the same name.

2007: DiCaprio produces Gardener of Eden and The 11th Hour

In 2007, Leonardo DiCaprio produced the comedy drama "Gardener of Eden" and also produced, co-wrote, and narrated "The 11th Hour", a documentary on the state of the natural environment.

2007: Won bidding war for Jordan Belfort's memoir rights

In 2007, Leonardo DiCaprio won a bidding war against Warner Bros., Brad Pitt, and Paramount Pictures for the rights to Jordan Belfort's memoir. This memoir would eventually become the basis for the film "The Wolf of Wall Street".

2008: Appian Way Productions and Greensburg

From 2008 to 2010, Appian Way Productions, founded by Leonardo DiCaprio, produced the documentary series Greensburg.

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2008: The 11th Hour wins Earthwatch Environmental Film Award and DiCaprio stars in Body of Lies

In 2008, "The 11th Hour" won the Earthwatch Environmental Film Award. Also in 2008, DiCaprio starred in "Body of Lies," a spy film where he played an agent battling a terrorist organization. DiCaprio also produced Planet Green's Greensburg.

2008: Appian Way produced Farragut North

In 2008, Beau Willimon wrote the play Farragut North, which was later adapted into the 2011 film The Ides of March produced by DiCaprio's Appian Way.

2008: DiCaprio and Winslet reunite in Revolutionary Road

In 2008, Leonardo DiCaprio collaborated with Kate Winslet in "Revolutionary Road," directed by Sam Mendes. Winslet suggested they work together on a film adaptation of the 1961 novel by Richard Yates. DiCaprio earned his seventh Golden Globes nomination for the film.

2008: Performance in Revolutionary Road

In 2008, Leonardo DiCaprio starred in the romantic drama Revolutionary Road.

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2008: Inspired by financial crisis to make "The Wolf of Wall Street"

In 2008, Leonardo DiCaprio was inspired by the financial crisis to make the film "The Wolf of Wall Street", based on the autobiography of Jordan Belfort.

2008: Vanity Fair labels DiCaprio and Winslet as 'Hollywood's most iconic screen couple'

In 2008, Vanity Fair described Leonardo DiCaprio and Kate Winslet as "Hollywood's most iconic screen couple" since Humphrey Bogart and Ingrid Bergman, solidifying their on-screen partnership's impact.

2009: DiCaprio produces Orphan

In 2009, Leonardo DiCaprio produced the psychological horror thriller film "Orphan."

2010: Appian Way Productions and Greensburg

From 2008 to 2010, Appian Way Productions, founded by Leonardo DiCaprio, produced the documentary series Greensburg.

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2010: DiCaprio stars in Inception

In 2010, Leonardo DiCaprio starred in Christopher Nolan's "Inception", inspired by lucid dreaming and dream incubation. 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. DiCaprio earned $50 million from the film, becoming his highest payday yet.

2010: Greensburg ends

In 2010, Planet Green's Greensburg, produced by Leonardo DiCaprio, ended after running for three seasons.

2011: Starred in J. Edgar and Produced Red Riding Hood and The Ides of March

In 2011, Leonardo DiCaprio starred as J. Edgar Hoover in the biopic "J. Edgar", produced the romantic horror film "Red Riding Hood", and his company Appian Way produced the political drama "The Ides of March".

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2012: Starred in Django Unchained

In 2012, Leonardo DiCaprio starred as Calvin Candie in Quentin Tarantino's "Django Unchained". Despite initial discomfort with the film's racism, DiCaprio continued filming after cutting his hand on glass, with Tarantino electing to use that take. The film was critically acclaimed and earned DiCaprio a Golden Globe nomination.

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January 2013: Announced break from acting and starred in The Great Gatsby

In January 2013, Leonardo DiCaprio announced he would take a break from acting to focus on environmental work. Also in 2013, he starred as Jay Gatsby in Baz Luhrmann's "The Great Gatsby", which garnered mixed reviews but praised his performance.

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2013: National Board of Review Spotlight Award

In 2013, Leonardo DiCaprio and Martin Scorsese earned the National Board of Review (Spotlight Award) for their collaborations.

2013: Role in The Wolf of Wall Street

In 2013, Leonardo DiCaprio starred in the biopic The Wolf of Wall Street.

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April 2014: Virunga premiered at Tribeca Film Festival

In April 2014, the documentary film "Virunga", for which Leonardo DiCaprio was an executive producer, premiered at the Tribeca Film Festival.

2015: Rolling Stone article calls Titanic DiCaprio's best role

In 2015, Ebiri, in his Rolling Stone article, praised Leonardo DiCaprio's role in "Titanic" as his best. He highlighted the genuine emotion conveyed by DiCaprio and Winslet in their performances, drawing viewers into their love story.

2015: Produced and starred in The Revenant

In 2015, Leonardo DiCaprio produced and starred in Alejandro G. Iñárritu's survival drama "The Revenant" as fur trapper Hugh Glass. The role was physically demanding, requiring him to eat raw bison liver and sleep in animal carcasses. His performance earned him numerous awards, including an Academy Award, BAFTA, Critics' Choice, Golden Globe, and SAG Award for Best Actor.

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2015: Academy Award for The Revenant

In 2015, Leonardo DiCaprio won the Academy Award for Best Actor for his role in the survival drama The Revenant.

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2016: Executive producer for The Ivory Game and Catching the Sun

In 2016, Leonardo DiCaprio was an executive producer for "The Ivory Game" and "Catching the Sun". He also produced, hosted, and narrated the documentary "Before the Flood" about climate change.

2018: Produced Delirium and Robin Hood

In 2018, Leonardo DiCaprio's production ventures included the psychological horror "Delirium" and the action-adventure "Robin Hood".

2019: Box Office Grosses and Rankings

As of 2019, Leonardo DiCaprio's films have grossed over $7.2 billion worldwide. In 2019 he has been placed eight times in annual rankings of the world's highest-paid actors.

2019: Role in Once Upon a Time in Hollywood

In 2019, Leonardo DiCaprio starred in the comedy-drama Once Upon a Time in Hollywood.

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2019: Returned to acting in Once Upon a Time in Hollywood

In 2019, after a four-year break from acting, Leonardo DiCaprio starred in Quentin Tarantino's "Once Upon a Time in Hollywood" as Rick Dalton. The film premiered at the 2019 Cannes Film Festival and received critical praise for DiCaprio's performance.

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2020: Executive producer for The Right Stuff and appeared in The Last Dance

In 2020, Leonardo DiCaprio served as an executive producer for "The Right Stuff", a television series adaptation of the 1973 book of the same name. He also briefly featured in the finale of the miniseries "The Last Dance".

2021: Starred in Don't Look Up

In 2021, Leonardo DiCaprio starred in Adam McKay's satirical comedy "Don't Look Up" alongside Jennifer Lawrence. He saw the film as an analogy for the world's indifference to the climate crisis.

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2023: Starred in Killers of the Flower Moon

In 2023, Leonardo DiCaprio starred in Martin Scorsese's crime drama "Killers of the Flower Moon", based on the book of the same name by David Grann. DiCaprio insisted on playing the morally complex role of murderer Ernest Burkhart. His performance earned him another Golden Globe nomination.

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