Steven Spielberg directed and produced Catch Me If You Can, a 2002 American biographical crime film. The film is based on Frank Abagnale's memoirs, in which he claimed to have pulled off multimillion-dollar con jobs while posing as a Pan American World Airways pilot, a Georgia doctor, and a Louisiana parish prosecutor before turning 19. His story's validity is still questionable.

Catch Me If You Can rank ninth in box office receipts in 2002. It was released on December 25, 2002, and grossed slightly more than $30 million in 3,225 theaters in its first weekend, placing it second behind The Lord of the Rings: The Two Towers. Catch Me If You Can has a 96 percent "certified fresh" rating on Rotten Tomatoes, based on 203 reviews with an average rating of 7.90/10. The site's critical consensus reads: "With help from a strong performance by Leonardo DiCaprio as real-life wunderkind con artist Frank Abagnale, Steven Spielberg crafts a film that's stylish, breezily entertaining, and surprisingly sweet."

Detailed Information:

Directed by: Steven Spielberg

Starring: Leonardo DiCaprio, Tom Hanks, Christopher Walken, Martin Sheen

Release dates: December 18, 2002 (Westwood)/December 25, 2002 (United States)
Running time: 141 minutes

Martin Scorsese directed and William Monahan wrote The Departed, a 2006 American epic criminal thriller film. It's a remake of the 2002 Hong Kong film Infernal Affairs. While joining an Irish gang in South Boston, an undercover officer and a police mole seek to identify each other. Each individual is occupied by his double life, acquiring intelligence on the operations they have infiltrated's plans and counter-plans. However, as it becomes evident to both the mob and the police that there is a mole among them, Billy and Colin find themselves in jeopardy of being discovered and exposed to the enemy - and each must race to discover the identity of the other guy in time to rescue themselves.

The Departed was a critical and commercial success, winning a number of awards, including four Academy Awards at the 79th Academy Awards. For his performance, DiCaprio was nominated for a Golden Globe Award for Best Actor – Motion Picture Drama (he was also nominated that year for Blood Diamond in the same category), a BAFTA Award for Best Actor in a Leading Role, and a Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Supporting Role.

Detailed Information:

Directed by: Martin Scorsese

Starring: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg

Release dates: September 26, 2006 (Ziegfeld Theatre)/October 6, 2006 (United States)
Running time: 151 minutes

What's Eating Gilbert Grape is a 1993 American coming-of-age drama film. It is a gorgeously photographed film about sensitivity, care, and self-awareness set in the fictitious working-class village of Endora. The story revolves around Ellen and Amy Grape, as well as their two brothers Arnie and Gilbert, and their grossly obese widowed mother Bonnie Grape, who are attempting to live and coexist with the loss of a father figure, low-wage job, and seventeen-year-old Arnie's serious mental illness.

The film received positive reviews, with DiCaprio's performance receiving widespread praise. The 19-year-old was nominated for his first Academy Award and Golden Globe Award nominations for Best Actor in a Supporting Role, making him the seventh-youngest Best Supporting Actor nominee the latter.

Detailed Information:

Directed by: Lasse Hallström

Starring: Johnny Depp, Leonardo DiCaprio, Juliette Lewis, Mary Steenburgen

Release date: December 17, 1993
Running time: 118 minutes

James Cameron directed, wrote, produced, and co-edited Titanic, a 1997 American epic romance and catastrophe film. 84 years later, on the Keldysh, a 100-year-old woman named Rose DeWitt Bukater tells her granddaughters about her life on the Titanic, which began on April 10th, 1912, when young Rose boarded the ship with the upper-class passengers. Jack Dawson, a drifter and artist, and his closest buddy win third-class tickets to the ship. And she recounts the entire story from the ship's departure to its sinking on April 15th, 1912 at 2:20 a.m. on its first and final trip.

Titanic was a critical and commercial success when it was released on December 19, 1997, and it has since won countless honors. It received 14 Oscar nominations, tying All About Eve (1950) for the most, and won 11 of them, including Best Picture and Best Director, tying Ben-Hur (1959) for the most Oscars won by a single film. Titanic was the first film to break the $1 billion mark with a worldwide total of nearly $1.84 billion. Until Cameron's Avatar overtook it in 2010, it was the highest-grossing film of all time.

Detailed Information:

Directed by: James Cameron

Starring: Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates

Release dates: November 1, 1997 (Tokyo)/December 19, 1997 (United States)/December 20, 1997 (South Africa)
Running time: 195 minutes

Django Unchained is a 2012 American Revisionist Western film written and directed by Quentin Tarantino. In 1858, a bounty hunter named King Schultz seeks out and purchases a slave named Django in order to locate the persons he is seeking for. Django wants to track down his wife, Broomhilda, who was sold separately from him by his former owner for attempting to flee. If he chooses to stay with him and be his partner, Schultz promises to assist him. They eventually find that she was sold to a Mississippi plantation. They devise a strategy to get the owner to invite them into his house and allow them to find a way to save her.

Django Unchained had its world premiere on December 11, 2012, at the Ziegfeld Theatre in New York City, and was released theatrically on December 25, 2012, in the United States, grossing over $425 million worldwide against a budget of $100 million, making it Tarantino's highest-grossing film to date. The film won multiple honors and nominations, including five nods for Best Picture at the 85th Academy Awards.

Detailed Information:
Directed by: Quentin Tarantino
Starring: Jamie Foxx, Christoph Waltz, Leonardo DiCaprio, Kerry Washington
Release dates: December 11, 2012 (Ziegfeld Theatre), December 25, 2012 (United States)
Running time: 165 minutes

Christopher Nolan wrote and directed the 2010 science fiction action film Inception, which he also produced with his wife, Emma Thomas. Leonardo DiCaprio plays a skilled thief who steals business secrets through dream-sharing technology is tasked with planting an idea in the head of a C.E.O., but his tragic past may doom the endeavor and his crew to failure.

The premiere of Inception took place on July 8, 2010 in London, and it was released on July 16, 2010 in both conventional and IMAX cinemas. Inception was the fourth-highest-earning picture of 2010, grossing over $828 million worldwide. It won four Academy Awards (Greatest Cinematography, Best Sound Editing, Best Sound Mixing, and Best Visual Effects) and was nominated for four more: Best Picture, Best Original Screenplay, Best Art Direction, and Best Original Score. It is widely regarded as one of the best films of the decade.

Detailed Information:
Directed by: Christopher Nolan
Starring: Leonardo DiCaprio, Ken Watanabe, Joseph Gordon-Levitt, Marion Cotillard
Release dates: July 8, 2010 (Odeon Leicester Square)/July 16, 2010 (the United States and the United Kingdom)
Running time: 148 minutes

Martin Scorsese directed and John Logan wrote The Aviator, a 2004 American epic biographical drama film. The film follows the life of Howard Hughes, an aviation pioneer and director of the film Hell's Angels, and is based on the non-fiction book Howard Hughes: The Secret Life by Charles Higham, published in 1993. Hughes' life is chronicled in the film from 1927 to 1947, during which time he became a wealthy film producer and aviation tycoon while also becoming more unstable as a result of severe obsessive-compulsive disorder (OCD).

On a budget of $110 million, it earned $214 million and received several awards. At the 11th Screen Actors Guild Awards, DiCaprio was nominated for Outstanding Male Actor in a Leading Role, while Blanchett won Outstanding Female Actor in a Supporting Role.

Detailed Information:
Directed by: Martin Scorsese
Starring: Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale, John C. Reilly
Release dates: December 14, 2004 (New York City)/December 25, 2004 (United States)
Running time: 170 minutes

Quentin Tarantino's comedy-drama film Once Upon a Time... in Hollywood is a 2019 comedy-drama film written and directed by him. It is a co-production between the United States, the United Kingdom, and China. The film follows a TV star Rick Dalton (Leonardo DiCaprio) and his longtime stunt double Cliff Booth (Brad Pitt) strive to achieve fame and success in the final years of Hollywood's Golden Age in 1969 Los Angeles. It features "multiple storylines in a modern fairy tale tribute to the final moments of Hollywood's golden age."

The film was named one of the top ten films of the year by the American Film Institute and the National Board of Review, among other honors. It got ten Academy Award nominations, including Best Picture, and won Best Supporting Actor (Pitt) and Best Production Design at the 92nd Academy Awards. At the 77th Golden Globe Awards, it also won Best Motion Picture – Musical or Comedy, Best Screenplay, and Best Supporting Actor (Pitt).

Detailed Information:

Directed by: Quentin Tarantino

Starring: Leonardo DiCaprio, Brad Pitt, Margot Robbie, Emile Hirsch

Release dates: May 21, 2019 (Cannes)/July 26, 2019 (United States)/August 14, 2019 (United Kingdom)
Running time: 161 minutes

Jerry Zaks directed Marvin's Room, a 1996 American drama film. The script was created by John Guare and was based on Scott McPherson's play of the same name, which he died in 1992. Marvin's Room, according to critics, stands out from the crowd of dysfunctional family dramas because of a strong ensemble that includes Meryl Streep, Diane Keaton, and Leonardo DiCaprio.

Bessie (Diane Keaton) and Lee (Meryl Streep) are sisters who have been separated for over two decades owing to their polar opposite personalities and life paths. Bessie stayed in Florida to care for their bedridden father (Hume Cronyn), while Lee married and had a family in Ohio. However, Bessie's doctor (Robert De Niro) has diagnosed her with leukemia and advised her that she requires a bone marrow transplant. Lee's troubled son (Leonardo DiCaprio) and Bessie's prognosis lead to an unexpected family reunion.

The Wolf of Wall Street is a biographical criminal dark comedy film directed by Martin Scorsese and written by Terence Winter, based on Jordan Belfort's 2007 memoir of the same name. It tells the story of Belfort's career as a stockbroker in New York City and how his business, Stratton Oakmont, was engaged in widespread corruption and fraud on Wall Street, eventually leading to his downfall. Belfort is played by Leonardo DiCaprio, who also produced the film. Jonah Hill plays his business partner and buddy Donnie Azoff, Margot Robbie plays his wife Naomi Lapaglia, and Kyle Chandler plays FBI agent Patrick Denham, who seeks to bring Belfort down.

It was nominated for a total of five Academy Awards, including Best Picture, Best Director, Best Adapted Screenplay, Best Actor (for DiCaprio), and Best Supporting Actor at the 86th Academy Awards ceremony (for Hill). At the 71st Golden Globe Awards, Leo won Best Actor – Musical or Comedy, while the film was nominated for Best Picture – Musical or Comedy.

Detailed Information:
Directed by: Martin Scorsese
Starring: Leonardo DiCaprio, Jonah Hill, Margot Robbie, Matthew McConaughey
Release dates: December 17, 2013 (Ziegfeld Theatre)/ December 25, 2013 (United States)
Running time: 180 minutes