Top 10 Classic Movies Every Entrepreneur Should Watch

The Merchant of Venice (2004) tells the story of Bassanio, a young nobleman who must borrow money from the Jewish moneylender Shylock (played by Al Pacino) to resolve his financial troubles. The film offers insightful lessons about business partnerships, risk assessment, and enduring principles that remain relevant today.

Bassanio, a nobleman from Venice, wishes to marry the beautiful Portia from Belmont, who stands to inherit a large fortune. Having squandered his own wealth, he needs 3,000 ducats to pursue her. Bassanio turns to his wealthy friend Antonio, a Venetian merchant who has often helped him before. Antonio agrees to assist but, being cash-strapped due to his ships still being at sea, offers his name as collateral for the loan. As a result, Bassanio approaches the moneylender Shylock, who agrees to lend the sum on the condition that Antonio guarantees the loan.

IMDb Rating: 7.0
Tomatometer: 72%
Audience Score: 72%

Contrary to what its title might suggest, the film Thank You for Smoking does not promote or encourage smoking. The film presents a satirical and humorous narrative centered on Nick Naylor, a spokesman for a tobacco company.

Nick's job involves lobbying and executing advertising campaigns to increase cigarette sales. Naturally, it isn't easy to convince the public to buy more cigarettes. Nick uses his persuasive speaking skills to push his agenda, even attempting to convince children at a school presentation that smoking isn't as bad as it's portrayed.

On the surface, Nick may appear as an unsavory character, and you might feel reluctant to watch the film. However, as you follow Nick's story, it's difficult not to sympathize with him. This movie offers a sharp insight into marketing and human psychology—how easily people can be persuaded and the fragile nature of our convictions. At the heart of marketing is the ability to connect with customers, understand their needs, and deliver the right message. Ultimately, it's not the product but the understanding of the audience that drives success in marketing.

IMDb Rating: 7.5
Tomatometer: 86%
Audience Score: 87%

Up in the Air is a 2009 American comedy-drama film directed by Jason Reitman and written by Reitman and Sheldon Turner, based on the novel by Walter Kirn. The story follows Ryan Bingham (George Clooney), a professional who specializes in firing employees for various companies, and his journey throughout his travels. The film highlights his lonely lifestyle and the philosophies he shares with those he encounters along the way.

The plot centers on Ryan Bingham (George Clooney), a corporate downsizer who spends most of his time flying first class across the country to lay off employees. His personal goal is to accumulate 5 million miles of air travel. His life takes a turn when a young woman introduces a policy of conducting layoffs via webcam, which threatens Ryan's entire approach to his work. He must prove that firing people requires a personal touch, one that can't be replicated by technology.

This film serves as a valuable lesson for managers, emphasizing the importance of prioritizing people over machines in business growth.

You may be familiar with Facebook and may even be addicted to the app, but do you know the story behind the creation of this multi-billion-dollar platform? Watch The Social Network to uncover the brilliant mind behind Facebook and his journey as a student at the prestigious Harvard University. The film also delves into the personal life and romantic relationships of Mark Zuckerberg, the founder of Facebook.

The Social Network is a 2010 psychological drama about the creation of the social media giant Facebook. The screenplay, written by Aaron Sorkin, is based on the book The Accidental Billionaires by Ben Mezrich, and the film was directed by David Fincher. Jesse Eisenberg stars as Mark Zuckerberg, alongside Andrew Garfield and Justin Timberlake. While the film faced criticism for inaccuracies regarding Zuckerberg's personal life and the creation of Facebook, it has received widespread praise for its direction, acting, editing, and especially its screenplay. The movie won multiple awards, including Best Drama at the Golden Globe Awards, along with Best Director, Best Screenplay, and Best Original Score.

IMDb Rating: 7.8
Tomatometer: 96%
Audience Score: 87%

Margin Call takes place during the early days of the 2007-2008 financial crisis, focusing on a major Wall Street investment bank. Two junior financial analysts, Seth Bregman and Peter Sullivan, discover a way to save the bank from collapse within 36 hours. However, they struggle to convince their boss to act on the information. Will they be able to avert disaster and save the company?

The film captures the essence of 1980s capitalism at its peak, with the infamous mantra 'Greed is good' still resonating in today's economic landscape. It offers a fascinating, fictional look at the destructive power of greed, and how it can lead to financial ruin.

Margin Call provides a sharp portrayal of the U.S. financial crisis of 2008, winning the Oscar for Best Original Screenplay. Through its gripping narrative, the film highlights the costly mistakes that business leaders often make, leading to unforeseen consequences. Despite its length, the film is filled with valuable business lessons, and its surprising twists make it one of the most highly regarded films of all time.

Too Big to Fail is a biographical drama that first aired on HBO on May 23, 2011. Based on Andrew Ross Sorkin's non-fiction book, it recounts the events of the 2008 financial crisis. Directed by Curtis Hanson, the film received 11 nominations at the 63rd Primetime Emmy Awards.

The film takes viewers on a journey through a U.S. economy teetering on the brink of collapse in 2008. In the mid-2000s, Wall Street saw record-breaking commissions, multimillion-dollar salaries, and a booming real estate market. Key figures such as Treasury Secretary Hank Paulson, Federal Reserve Chairman Ben Bernanke, and New York Federal Reserve President Timothy Geithner played pivotal roles in preventing a global crisis like no other.

Though the film was a box office success upon its release, its impact continues to resonate today, influencing both the film industry and business professionals worldwide.

Steve Jobs is a 2015 biographical drama directed by Danny Boyle with a screenplay by Aaron Sorkin. Based on the biography by Walter Isaacson and interviews conducted by Sorkin, the film unfolds across three acts over fourteen years (1984–1998) in the life of Steve Jobs, the co-founder of Apple Inc. and the visionary behind personal computing.

The movie follows Jobs, a revolutionary figure who reshaped the tech world. Known for his relentless innovation and profound philosophy of life, Jobs is admired by millions. One of his most iconic moments, his commencement speech at Stanford University, is remembered for the words “Stay hungry, stay foolish,” inspiring countless young people around the world to pursue their passions.

This film dives deep into the life of a global legend, revealing both the public triumphs and personal struggles of the man behind Apple, including his initial refusal to publicly acknowledge his daughter.

IMDb Rating: 7.2
Tomatometer: 85%
Audience Rating: 73%

Citizen Kane is a 1941 American film directed by Orson Welles, who also co-wrote the screenplay with Herman J. Mankiewicz. The movie is a fictionalized biography of Charles Foster Kane, a media mogul based loosely on the life of real-life media baron William Randolph Hearst, with additional details drawn from Welles’ own life.

The film follows the rise and fall of Kane, a fictional character who becomes one of the wealthiest men in the world. Born into poverty, Kane’s life changes dramatically when his mother inherits a valuable mine, leading her to send him to live with a wealthy guardian. As an adult, Kane uses his vast fortune to build a powerful media empire with the help of two loyal colleagues, Bernstein and Jedediah Leland. Though he succeeds in business, his personal life crumbles as he divorces twice and dies in isolation at his opulent Xanadu estate, with his last words being “Rosebud.”

IMDb Rating: 8.3
Tomatometer: 99%
Audience Rating: 90%

Death of a Salesman is a 1985 American film adaptation of Arthur Miller's 1949 play. Directed by Volker Schlöndorff, it stars Dustin Hoffman, Kate Reid, John Malkovich, Stephen Lang, and Charles Durning. The film stays true to the original script and was first aired on CBS on August 16, 1985. It earned 10 Emmy nominations at the 38th Primetime Emmy Awards and 4 Golden Globe nominations at the 43rd Golden Globe Awards, winning 3 Emmys and 1 Golden Globe.

The plot revolves around Willy Loman and his wife Linda. Willy believes that he and his family are destined for success. However, as he tirelessly works as a salesman, he begins to lose touch with reality, drifting into his past. Meanwhile, his wife Linda and their sons, Biff and Happy, try to cope with Willy's self-destructive tendencies and the haunting memories of his past. The family is forced to leave their home and rent a new one from one of Willy's colleagues, unaware that the house was once used by a prostitute.

IMDb Rating: 7.2
Tomatometer: 100%

Audience Rating: 75%

Glengarry Glen Ross (The Art of Sales) is a 1992 film that offers a gritty look at real estate salesmen. Starring Jack Lemmon, Alec Baldwin, Kevin Spacey, Ed Harris, Jonathan Pryce, and Al Pacino, the film showcases the cutthroat nature of the industry. Al Pacino's performance earned him an Academy Award nomination for Best Supporting Actor.

The film is a must-watch at least once in your life for anyone interested in sales tactics and business strategy. The story follows a real estate office manager who motivates his staff with extravagant rewards for top sales but threatens harsh consequences for underperformers.

Set during a dark economic downturn in New York, the office environment reflects this gloom, with salesmen competing for a Cadillac Eldorado as the top prize. The second prize is a steak knife set, and third place results in being fired. With foul language, abrasive characters, harsh weather, and deceitful business practices, the film portrays a brutal reality of sales.

This movie is an insightful exploration of competition and survival in the corporate world. It delivers valuable lessons in sales techniques, customer relationship management, negotiation, and dealing with the looming threat of failure.

IMDb Rating: 7.7
Tomatometer: 95%
Audience Rating: 88%