The 25 Greatest Directorial Debuts by Actors-Turned-Directors

9. The Indian Runner (Sean Penn, 1991)


It is no surprise that the movies directed by Sean Penn are very, very good. Hollywood bad-boy turned left-wing intellectual has included in his circle of friends noted literates like William Burroughs, Charles Bukowski or Hunter Thompson.

Sean Penn has always believed that films should be more than entertainment; films should educate, cultivate and open mind. This message comes across very strong in all the movies he has directed. His first movie as a director – “The Indian Runner” – is a gripping tales of two brothers on the opposite spectrums of life.

Joe Roberts (David Morse) is a small town deputy sheriff, quiet, down to Earth who is at peace with his job as it is a way to support his wife Maria. His brother Frank Roberts (Viggo Mortensen) is a violent criminal who fought the Vietnam War only to escape doing prison.

On his return home Frank clashes with his brother and with the whole world around him as it seems he cannot adapt. In the role of the father of the boys we have a moustache-less Charles Bronson (in his last film that wasn’t part of the “Death Wish” series) who pulls off the greatest role of his later career.

There is something special about this film; the script is based on a Bruce Springsteen song, the two lead actors were unknown at the time and have since become respected in their craft and finally it remains open to any kind of interpretation: from the classic good versus evil case to the argue that the two brothers represent the two sides of Sean Penn’s personality. Whatever the explanations, “The Indian Runner” remains a classic staple of independent cinema.


10. Mr. Saturday Night (Billy Crystal, 1992)

MR. SATURDAY NIGHT, Billy Crystal, 1992

When asked for advice almost every writer will tell you the following: write about what you know. Seems to be the case with Billy Crystal who’s first film examines the world that which he knows best: the world of comedy. This heartwarming film tries exposes all the aspects of being a funny man for a living.

Unlike films like “Lenny” this movie doesn’t take itself to serious all the time allowing the audience a good laugh while mixing in some serious issues as well. The film is about a fictional comedian named Buddy Young Jr. (Billy Crystal) who struggles for stardom. He starts of as a stand-up comedian but then gradually evolves into television until becoming a fairly successful star. As his career rises so does his ego pushing everyone away him.

Eventually Buddy’s career stars to decline leaving him to confront his demons and the people he has alienated from. The only one that sticks by his side through the good times and the bad times is his brother and manager Stan (David Paymer). This small film is a very well-crafted film that is guaranteed to steal your laughs and tears.


11. Bob Roberts (Tim Robbins, 1992)

Bob Roberts

In 1986 Tim Robbins did a sketch for “Saturday Night Live” involving the singing politician Bob Roberts. In the early 90’s he began toying with the idea of turning that short segment into a feature film with him starring and directing. Because no studio would touch his project Robbins did the film independently asking his actor friends to do the movie for free.

Everybody came through for him; more than that Alan Rickman even put up his own money to finance the film. And so the quirky political musical “Bob Roberts” was born. Shot documentary style the movie follows the political race of fictional folk singer Bob Roberts (Tim Robbins), who aspired to one day become a senator for the state of Pennsylvania.

Roberts is looking to capitalize on his stardom as a singer in order to get elected. Roberts travels the state holding concerts instead of speeches and autograph sessions instead of press conferences. Roberts is a Republican and he lets this fact be known by inserting conservative messages in his songs. There are a lot of star actors and actresses appearing in this film – all of them worked for free as a favor to Robbins. If you are fan of the mockumentary genre this film is not to be missed.


12. A Bronx Tale (Robert De Niro, 1993)

A Bronx Tale

When you think of Robert De Niro in the late 70’s, early 80’s you immediately think of Martin Scorsese. The actor/director pair remains one of the best in the world. They have made 8 films so far;all of them truly great. So it is no surprise that De Niro’s directorial debut draws huge influences from the legendary Scorsese.

Alas the source material is not something that De Niro or Scorsese wrote (though viewing the film you might be tempted to think so) but a one-man show written and developed by actor Chazz Palminteri. The actor performed his show in local clubs and became rather successful.

De Niro saw the show and approached Palminteri about turning it into a movie. Palminteri agreed with the condition the he could write the script and play the central adult character in the movie…and so “A Bronx Tale” was born. The film is a coming of age story and its central character is a young Italian-American boy named Calogero.

Growing up in the Bronx Calogero is exposed to the local mafia and its violence from a very early age. Despite his fathers’ (Robert De Niro) wishes to keep him away from all this Calogero is fascinated by this world, especially its leader Sonny (Chazz Palminteri) – a charismatic but ruthless mob boss. Ironically Sonny teaches the young boy more about life than his own father and shapes him into becoming a man the proper way. A fascinating film overflowing a lot of talent and passion from everyone involved.


13. Reality Bites (Ben Stiller, 1994)

Reality Bites (1994)

The early 90’s were a very prolific time for youth films. There was “Slacker”, “Dazed and Confused” and then there was “Reality Bites”. “Reality Bites” is sort of like the coda of Generation X; it tells the youths of Generation X that daydreaming is over and that it is time to enter the harsh realities of the grown up world.

The plot follows a young woman names Lelaina (Winona Ryder), an aspiring videographer working on a documentary about the dysfunctional and chaotic lives of her friends and roommates. She wants to call her film “Relity Bites” because it is her true belief shared by most of her friends.

In her path, for the truth about the life choices of Generation X, she meets coffe-house guitarist Troy (Ethan Hawke) and TV executive Michael (Ben Stiller); two very different men with different mentalities and different aspirations in life. Torn between two Lelaina is faced with her first big choice in life which she cannot afford to treat lightly.


14. Trees Lounge (Steve Buscemi, 1996)

Trees Lounge (1996)

“Trees Lounge” seems to preach the sweet life of the idle but underneath its characters’ laid-back attitude lies a universal lesson: don’t take life for granted. In a small town blue collar community former mechanic Tommy (Steve Buscemi) seems to take his life lessons from the local bar: “Trees Lounge”.

Tommy is a loveable loser that seems to come straight from the novels of Charles Bukowski. He makes mistake after mistake in both his professional and personal life but on one around him seems to mind and they have gotten use to him and learned to be indulgent. The audience gets the same feeling from watching this movie and roots for the underdog of the story to get his act together and makes things right.


15. Sling Blade (Billy Bob Thornton, 1996)

Sling Blade

Billy Bob Thornton fought real hard to get this movie made and it paid off as it was one of the most appreciated films of 1996. Thornton wrote the script in long hand in his home in Arkansas, in the early 90’s. Because he couldn’t get the script produced he turned into a short film and released it in 1994. The short film – whom Thornton directed and starred in – was called “Some Folks Call It a Sling Blade”.

The film was a success so money was found to produce a feature film that would become “Sling Blade” – again with Thornton starring and directing. “Sling Blade” proved to be a sleeper hit, with critics and audiences alike, winning an Oscar for best adapted screenplay and being nominated in the lead actor category.

The film is about and intellectually disabled man named Karl Childers (Billy Bob Thornton) who is released from a mental institution and must start his life all over again in small prejudice town. Karl has been in institutionalized most of his life for killing his mother and her lover at the age of 12.

Now a full grown man simple Karl has a very hard time coping with his new found freedom and with the way people perceive his past. The only one he really seems to communicate with is a twelve-year boy named Frank (Lucas Black). The film conveys a sympathetic look towards Karl and his fate and really opens eyes on the sad life of the disadvantaged.


16. Nil by Mouth (Gary Oldman, 1997)

Ray Winstone - “Nil by Mouth”

My, oh my! What a violent, disturbing yet brilliant film. Gary Oldman’s directorial debut is tailored around the environment he witness while growing up in working class London. The whole directorial tone of the film seems to come from Oldman’s on screen persona and the strange, scary characters he’s portrayed over the years.

The film is set in a poor working class London neighborhood and it focuses on the life of Valerie (Kathy Burke) and her abusive husband Ray (Ray Winstone). While Ray is perfectly happy with the life he’s living Valerie dreams on getting out and doing better for herself.

There seems to be no escape from misery and poverty for these people and the depressive black and white look of the film only deepens the anxiety of the viewer. Ray has a very short temper and often breaks into violent outbursts and Valerie does nothing but accept her fate.

This is not a film for the faint-hearted; the violent realism, as portrayed in this film, is almost unbearable to watch but the director felt it necessary in order to raise awareness of domestic violence. The title, “Nil by Mouth”, is a medical term instructing patients not to take any substances orally due to mouth damage. You draw your own conclusions.


17. The Winter Guest (Alan Rickman, 1997)

THE WINTER GUEST, Emma Thompson, Phyllida Law, 1997. ©Fine Line Features
©Fine Line Features

It is sad that this little gem has been forgotten by movie audiences. This is such a beautiful film capturing the spirit and the mood of life in highland Scotland.

The film follows the life of eight characters on a wintry day in Scotland: a mother and daughter (played by real life mother and daughter Phyllida Law and Emma Thompson), two young boys skipping school, two old gentlemen who have the morbid habit of frequenting strangers’ funerals, two bickering old women and two teenagers exploring life and love.

All these human interactions occur on the backdrop of an amazing set that is designed to look like a classical play. There is nothing fancy about this film – no explosions, special effects and elaborate conspiracy plots – but still it captures the imagination of the audience through its smart dialogue and credibility of human emotions.