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Oliver Stone: Directing, Screenwriting and Surviving the Vicious Hollywood Game

Today on the show I bring you one of the most influential and iconic writer/directors in the history of cinema, three-time Oscar® winner Oliver Stone. Throughout his legendary career, Stone has served as writer, director, and producer on a variety of films, documentaries, and television movies. His films have been nominated for forty two Oscars® and have won twelve.

Stone began his career as a screenwriter, though always had his eye on being a writer/director. He struggled years before being hired to write the true-life prison story Midnight Express, for which he won his first Oscar®. Stone further wrote Brian De Palma’sdrug lord epic Scarface, Year of the Dragon featuring Mickey Rourke, and John Milius’s Conan the Barbarian.

His first outing as a director was Seizure, an exploitation horror film he directed right out of film school, and the thriller The Hand, starring Michael Caine. Stone finally broke through as a director with his film Salvador, a violent look at the chaos of war as seen through the lens of an amoral photojournalist during the Salvadoran Civil War.

This is one of Stone’s most underrated works. It was critically acclaimed but commercially didn’t hit the mark.

After Salvador, he jumped right into directing Platton, the film that would catapult Stone into the stratosphere. Platoon would go on to be nominated for eight Academy Awards and won four including Best Picture, Best Director for Stone, Best Sound, and Best Film Editing.

Platoon was the first in a trilogy the Stone made about the Vietnam War, the other films were Born on the Fourth of July starring Tom Cruise and Heaven & Earth starring Tommy Lee Jones.

After Salvador Stone directed nine films in ten years. During that decade he created some of the most memorable films in cinematic history including the decade-defining Wall Street, JFK, The Doors, Natural Born Killers, and Nixon. 

Stone says his films are

“first and foremost dramas about individuals in personal struggles,”

and considers himself a dramatist rather than a political filmmaker. Politics definitely are a subject matter he enjoys making movies about. 2008’s W., a film about American President George W. Bush, was the first film in history released about a sitting president. This film wrapped up his trilogy on the presidency which he started with JFK and Nixon.

Stone’s filmography is peppered with notable films and masterpieces including 1997 road movie/film noir, U-Turn, 1999’s Any Given Sundaya film about power struggles within an NFL-style football team, and World Trade Center, based on the true story of survival during the September 11 attacks.

In 2004 Stone tackled another giant historical figure, Alexander the Great. His film Alexander, starring Colin Farrell, Anthony Hopkins, and Angelina Jolie, had a rough road and major studio interference.

Stone later re-edited the film into a two-part 3-hour 37-minute filmAlexander Revisited: The Final Cut, which later became a cash cow for Warner Brothersbecoming one of the highest-selling films in their back catalog.

In 2010, Stone directed his first-ever sequel, Wall Street: Money Never SleepsIn this film, he returns to Wall Street during the 2008 financial crisis. Famous onscreen villain Gordon Gekko Michael Douglas returns. Gekko teaches co-star Shia LaBeoufthe ins and outs of criminal investments.

Frost/Nixon’s Frank Langellaco-stars along with Susan Sarandon. I personally have a deep connection with his film Wall Street as it was the subject of the first short film I ever wrote, directed, and edited in high school.

Speaking to Oliver was a dream come true. Many of his films have impacted popular culture in a way that is uniquely his. During my time working at a video store, it seemed every film he released was a cultural bomb. Natural Born Killers was the first time I saw a modern director use multiple formats in one film.

His last film Snowden tackles the most important and fascinating true story of the 21st century. Snowden, the politically-charged, pulse-pounding thriller starring Joseph Gordon-Levitt and Shailene Woodley, reveals the incredible untold personal story of Edward Snowden, the polarizing figure who exposed shocking illegal surveillance activities by the NSA and became one of the most wanted men in the world.

He is considered a hero by some, and a traitor by others. No matter which you believe, the epic story of why he did it, who he left behind, and how he pulled it off makes for one of the most compelling films of recent years.

During our epic conversation, we discuss his legendary career, working with the Hollywood system, his time in Vietnam, struggling as a screenwriter, how he deals with rejection, and his amazing new book Chasing the Light: Writing, Directing, and Surviving Platoon, Midnight Express, Scarface, Salvador, and the Movie Game.

Chasing the Light is an intimate memoir by the controversial and outspoken Oscar-winning director and screenwriter about his complicated New York childhood, volunteering for combat, and his struggles and triumphs making such films as Platoon, Midnight Express, and Scarface.

Before the international success of Platoon in 1986, Oliver Stone had been wounded as an infantryman in Vietnam and spent years writing unproduced scripts while driving taxis in New York, finally venturing westward to Los Angeles and a new life.

Stone, now 73, recounts those formative years with in-the-moment details of the high and low moments: We see meetings with Al Pacino over Stone’s scripts for Scarface, Platoon, and Born on the Fourth of July; the harrowing demon of cocaine addiction following the failure of his first feature, The Hand (starring Michael Caine); his risky on-the-ground research of Miami drug cartels for Scarface; his stormy relationship with The Deer Hunter director Michael Cimino; the breathless hustles to finance the acclaimed and divisive Salvador; and tensions behind the scenes of his first Academy Award-winning film, Midnight Express.

Chasing the Light is a true insider’s look at Hollywood’s years of upheaval in the 1970s and ’80s. I highly recommend every filmmaker and screenwriter read this gem. Click here to read the book.

The main themes I took away from speaking to Oliver was struggle and fight. No matter how successful he got, no matter what heights he reached in Hollywood Oliver Stone had to fight to get each remarkable film in his filmography on the screen.

To this day he still gets rejected all the time. Throughout his career, he would jump from Hollywood studio to independent film. He wrote both Platoon and Born on the Fourth of July over a decade before they were produced because no one in Hollywood believed in what he was trying to say with those films. Platoon, The Doors, Midnight Express, Salvador, and Talk Radio were all indie films.

I hope this conversation inspires filmmakers and screenwriters to never give up. Oliver struggled for years taking jobs as a production assistant, cab driver, office assistant, and any other gig he could find to help him survive while he was chasing his dream. He wrote and wrote, meeting his goal of one to two screenplays a year, no matter what. Never give up, never surrender. As Oliver says

“Either you’re born crazy or you’re born boring.”

Enjoy my epic conversation with Oliver Stone.

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