30 Best Labor Day Movies of All Time

Labor Day movies don’t need to necessarily be connected to Labor Day but they comprise movies about work or the ones that happen in the working environment. They are often movies about workers and their struggle to survive as employees. They have to deal with various issues and these movies perfectly depict how individuals act in certain situations, sometimes completely desperate in all their attempts. This is the list of the 30 best Labor Day movies of all time.

Labor Day (2013)

Kate Winslet plays a depressed single mother Adele in this drama that deals with relationships between people, ones abandoned, sad, and convinced that everyone has forgotten about them. Adele and her son Henry meet an injured man and offer him a ride.

They soon learn he is a convict on the run and while the police roam around the town in search of him, Adele will form an unlikely bond with him during the Labor Day weekend and realize that people are not always as others present them.

The Grapes of Wrath (1940)

Based on one of the most beloved and important American novels of all time, John Steinbeck’s The Grapes of Wrath, this brilliant adaptation follows the Joad clan who is looking for a better life in California. After they lose their farm, they decide to travel to this promised land in the West, in search of a better life.

On the way there they meet an array of interesting families with the same plan, believing in the same dream. But as soon as they arrive in California, they quickly realize that it is nothing like they have imagined. 

Horrible Bosses (2011)

Nick, Dale, and Kurt are three employees who hate their bosses and instead of thinking about quitting their jobs, they begin to talk about how they would kill them. Nick works for an evil man who is constantly criticizing him but expects him to be always on time and work 24/7.

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Dale’s boss is Dr. Julia Harris, a predator who always makes unwelcome sexual remarks and comes on to him and Kurt is the only one satisfied with his boss until he dies and his psychopath son takes over. After a drunken night full of speculation they end up hiring a murder consultant who would help them pull off their deeds.

Working Girl (1988)

Melanie Griffith plays Tess McGill, a struggling actress who is trying to succeed in the ambitious and big business world of New York City. When her boss steals her business idea but breaks his leg on a skiing trip, she decides to steal it back and gain success.

She teams up with a cunning and charming investment broker Jack Trainer who will help her with her brilliant plan. Her idea is to pretend she has her boss’s job and after everything started perfectly, things are about to change drastically after her boss decides to return. 

9 To 5 (1980)

Judy, Violet, and Doralee work for a sexist, lying, and a hypocritical man named Franklin Hart who enjoys torturing his female employees. He always takes advantage of his female staff and is constantly making humiliating remarks about their work.

Violet is his top brilliant assistant who is fed up with this kind of behavior so she teams up with her co-workers Judy and Doralee with the idea to get back at him. But they end up kidnapping Franklin and now he is trapped in his own house.

Office Space (1999)

Office Space is another movie about employees who hate their bosses. This time we follow three company workers in the Initech office, Peter, Michael, and Samir who all hate everything connected to their job. Apart from professional, they have also personal issues and can’t wait for something to change.

After a series of unusual events and information that Samir and Michael will be downsized, they decide to plant a virus in the banking system to embezzle some money. But things don’t go as planned and they end up with too much money which they now need to figure out how to return, without getting caught and going to prison.

The Company Men (2010)

The Company Men drama features a stellar cast, including Ben Affleck, Tommy Lee Jones, Kevin Costner, and Chris Cooper and it shows us what are the consequences of losing a job and having to manage to deal with the fact that you are not needed somewhere but also with the lack of self worth.

Ben Affleck plays Bobby Walker who loses his job, together with the thousands of other employees when the huge GTX Corporation decides to cut jobs. We will follow his and two other men’s stories during a year in their life while struggling to keep their jobs and at the same time making everything work with their families and communities. 

Glengarry Glen Ross (1992)

This brilliant mystery crime-drama with Alec Baldwin, Jack Lemmon, and Al Pacino in leading roles tells the real story behind the world of sales. It shows how employees deal with the constant pressure in this line of work with all its ups and downs and highs and lows.

We follow days in a real estate agency where and witness what kind of moves workers have to do, what impacts their success, and in what way they are responsible for the things that happen at the office and if it affects them in any way.

Erin Brokovich (2000)

Erin Brokovich is one of Julia Roberts’ best roles in this true story about an unemployed single mother who desperately wants to find work but without any luck. Somehow she manages to get a job but since no one is taking her seriously, she decides to take things into her own hands.

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She begins to investigate a suspicious case involving a major firm which ends up in one of the biggest lawsuits in American history against a multi-billion dollar corporation. She discovered that the company was dumping illegal toxic waste poisoning the residents of the area around it. 

Clerks (1994)

This comedy is Kevin Smith’s first written and directed movie and it introduces us to his quirky characters and original storytelling. It follows one day in the lives of Dante and Randal, two convenience clerks. They both hate their jobs, Dante in a small convenience store and Randal in a video store next door.

They spend their day discussing life and its problems, including girlfriends, bosses, and life in general. They have both lost track and want to get back on it but don’t know how. So they decide to spend one day annoying customers, talking about movies, and playing hockey on the store roof.

Trading Places (1983)

One of the cult 1980s comedies is this excellent movie about Louis Winthorpe, a businessman for a successful firm called Duke and Duke where they are at the moment discussing the fact that there are various elements, such as a person’s environment, which determine how well you do in your life.

After bumping into a street hustler named Billy Ray Valentine and getting him arrested, he becomes his bosses’ guinea pig when they decide to switch his and Valentine’s places and test their company’s premises. 

Parasite (2019)

Parasite is one of the best South Korean movies of all time and the winner of numerous Oscars. Parasite is a thriller drama that perfectly depicts the differences between classes in this interesting country. We follow the poor Kim clan a the wealthy Park family and how their lives get intertwined after a trick has gone bad.

Kim’s son is a smart wanna-be student who has no prospects in life due to his poor family situation and the way of living in a shabby part of Seoul. When he takes the job of an English tutor at the park’s family mansion, he doesn’t even imagine what kind of life he and his family are going to be living in a few months. And even though it looked perfect at the beginning, it will soon become a nightmare for everyone.

The Wolf of Wall Street (2013)

The Wolf of Wall Street is Martin Scorsese’s masterpiece, a biographical crime drama based on the true story of Jordan Belfort and his rise to a wealthy stockbroker. He and his friend Donny Azoff started a brokerage firm and very soon became one of the most successful on Wall Street.

But as they became richer and wealthier, so are their appetites got bigger and they are eager to earn more money. Bank accounts in Europe and lavish parties with enormous amounts of liquor and drugs are becoming normal things for them but how long will they be able to escape the FBI’s constant monitoring?

Up in the Air (2009)

Up in the Air is a comedy-drama directed by Jason Reitman and tells the story of Ryan Bingham (played by George Clooney), a corporate downsizing expert who enjoys his job and constant traveling while going around the country and firing people.

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But his life is about to change just when he has to reach ten million frequent flyer miles. He meets a frequent traveler just like him, a woman who soon becomes the woman of his dreams. Unfortunately, things won’t be as perfect as they were until then. 

North Country (2005)

This heartbreaking drama,North Country, is set in 1989 when Josey Aimes runs away from her abusive husband together with her two kids and returns to her hometown in Minnesota. She soon gets a job at a local mine which makes her father extremely mad since he is also working there and believes it is a man’s job only.

Unfortunately, her father is supported by her own mother and no one bothers that Joyed and her female co-workers are constantly harassed at their job, emotionally, sexually, and physically. But things might change after Josie decides to sue the company for sexual harassment.

Norma Rae (1979)

Sally Field is Norma Rae, a young single mother who works in a local textile mill just like many members of her family before her. The working conditions at the factory are terrible and all of them are working long hours. Aware of all the dangers, she agrees to help unionize her mill, encouraged by the speech by a devoted labor activist Reuben.

Her decisions won’t be equally accepted by the people around her, especially her fiance and employers but despite these issues, she will risk everything and fight for what she believes is right. Field received an Oscar for her immaculate performance in this excellent movie.

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Dinner for Schmucks (2010)

Steve Carrel and Paul Rudd teamed up in this hilarious comedy about two completely different individuals who find themselves in a situation that ends up in something completely different than one of them expected.

Paul Rudd is Tim, a rising executive in a firm whose bosses arrange a monthly dinner for their employees and their plus one, being the biggest idiots they can find. Tim finds a “perfect” candidate in the form of IRS employee Barry, but as he befriends him, he begins to question the morale of the invitations and his company’s work ethics in general.

The Organiser (1963)

One of the many gems belonging to the brilliant Italian cinematography is this history-drama about the exploited factory workers from Turin, Italy at the turn of the 19th to 20 century. They team up with a former high school teacher who has turned unionist.

Professor Sinigaglia is allegedly sent by the Socialists to help those workers organize a strike to rebel against the inhuman conditions they are working in. He will be the one to support them in their struggle to gain their basic human rights, the ones to work in acceptable conditions.

Support the Girls (2018)

Support the Girls is a comedy-drama that centers on Lisa who works as general manager at Double Whammies and really loves her workplace and her customers. She is a devoted mother and a great worker who believes her company stands behind its motto.

But very soon her optimism will get shattered when she finds out that there is so much more to her work position and everything she does there and over the course of one strange day she will learn more about it than she has in all those years working there.

Newsies (1992)

Newsies is a Disney musical starring Christian Bale and Bill Pullman that is set in July 1899 and is inspired by the strike organized by the trolley workers. After the distribution price was raised, the already poor newsboys feel outraged and decided to rebel.

Led by Jack “Cowboy” Kelly as the voice and David Jacobs as the brains of the new union, the boys found the strength to join their forces and challenge the ones above them, the powerful without any sensitivity towards the small ones under them.

The Proposal (2009)

This interesting romantic comedy might give you a few laughs and a good time. Sandra Bullock plays Margaret, an editor for a New York publishing company, a strict boss to her assistant Andrew. When she finds out that her U.S. visa is soon to expire and she will be transported to Canada, she plots a scheme to marry Andrew. He agrees, but on his own terms, which include promotion. 

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And this is when comedy and romance start mixing, putting these two main characters into numerous funny situations which slowly start leading to much more than a mere quid pro quo deal. Sandra Bullock and Ryan Reynolds are a great match and a good choice for a movie of a sort.

Waitress (2007)

Kerri Russell is Jenny, an unhappily married woman who hopes to win a pie-baking contest in order to get money so she can leave her husband Earl. After finding out she is pregnant, her plans get awry and she decides to stay.

She works as a waitress at Joe’s diner where she bakes delicious pies and is overall satisfied but has to tolerate her boss Cal. Things finally change when a new doctor arrives in town so she can distract herself from her issues by checking on him with her fellow waitresses and friends. But as her pregnancy progresses, Earl becomes even more intolerable, and her way out of everything more and more distant.

Harlan County, USA (1976)

This heartbreaking documentary brings the story of the coal miners’ strike against the Brookside Mine in Harlan County, Kentucky in June 1973. It follows the thirteen-month struggle between a community and a  corporation that is reluctant to accept their offers.

Except for the issue addressed, the director Barbara Kopple gives us an insight into the background behind the plight of the miners and the history of the United Mine Workers of America).

The Salt of the Earth (1954)

This is another engaged biographical documentary, this time about the life and work of photographer Sebastiao Salgado who has spent the majority of his life documenting society in many hidden corners of the world.  

Salgado has been traveling from continent to continent over the last 40 years, in search of the most remarkable stories and breathtaking landscapes. He has witnessed some of the most important events of our recent history and now he is embarking on a journey to celebrate the Earth’s grandiosity and beauty. 

Modern Times (1936)

One of the greatest, most influential, and most important movies of all time is Charlie Chaplin’s last silent film, filled with sound effects. Here Chaplin turned against modern society and machine age and progress. In the beginning, he is selected for an experiment with an automatic feeding machine but after numerous mishaps, his boss begins thinking he has gone mad so he puts him into a mental institution. 

When he gets out, he is mistaken for a communist, with a red flag in his hand, and is sent to jail but very soon released. These are only some of his adventures in this classic where he wanted to express his views and feeling towards the great social and technological changes.

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Silkwood (1983)

Silkwood is a drama that was inspired by a true story about Karen Silkwood, the worker at an Oklahoma nuclear plant who discovered and wanted to go out in public with the story about the secret and dangerous practices at the Kerr-McGee plant.

But she was contaminated and psychologically tortured and possibly even murdered before she was able to expose worker safety violations at the plant she was working at. She died under suspicious and weird circumstances which are believed to be connected to her wanting to tell the truth.

Night Shift (1982)

After a great number of tv-movies, Ron Howard directed a comedy that made it to the big screens. This interesting movie tells the story of a morgue attendant who is forced to work a night shift with an obnoxious partner who dreams of success.

His life changes completely when his prostitute neighbor complains about losing her pimp and his partner suggests using the morgue at night as a brothel. After agreeing to it, he finds out that there are more people who have something against it besides his boss.

On the Waterfront (1954)

Elia Kazan directed one of the most important movies about workers and their fight for their rights in this crime drama thriller. The story is about Terry Malloy, a New Jersey longshoreman who wants to stand up to his corrupt union bosses, including his older brother.

After witnessing the murder committed by two thugs who worked for his boss, Terry meets the dead man’s sister and starts feeling responsible for  his death. She introduces him to Father Barry who wants to force him to provide information that will destroy the dock racketeers.

Bound for Glory (1976)

This is a brilliant biographical musical drama about Woody Guthrie, one of America’s most famous and beloved folk singers. He left his Texas home in the 1930s to try and find a job somewhere more promising. 

While struggling to get a job, he slowly began to realize what are all the obstacles a working-class man has to overcome to make it in this huge country, often extremely merciless to its own people.

Matewan (1987)

Matewan is a historical drama set in the 1920s in Mingo County, West Virginia. It is a story about coal miners who are struggling to form a union so they can fight against company operators of the Baldwin-Felts detective agency. 

The Italian and Afro-American workers are brought in by the company to break the strike but soon they will get together with the Ocala and form an even stronger union than anyone believed.

  • Tamara is a big movie, music and book fan since always and writes a blog about all these things. Loves psychological thrillers, noir movies and mysteries of all kind. Enjoys discussing and talking about movies and tv series.