Most Similar Movies to Chairman of the Board (1998)
If you are looking for movies like Chairman of the Board (1998), you might like movies tagged with keyword : comedy, business, workplace, inspirational, entrepreneurship, american film, 1990s, satire, humor, absurd, social commentary, power, wealth, dream, struggle, success, failure, satirical comedy, independent film, underdog .
The Associate (1996), Jimmy Hollywood (1994), Kill the Man (1999), Livin' Large! (1991), The Secret of My Success (1987), Entry Level (2007), The Disaster Artist (2017) ... Let's take a look at the following list...

The Associate (1996)
A comedy about making it on Wall Street. Prejudices are hard to break and Laurel Ayres quickly learns that in order for people to take her seriously she has to work for an older white man or be one.
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Jimmy Hollywood (1994)
A failing actor living in crime infested Los Angeles, frustrated with his career, decides to take the law into his own hands, and becomes the leader of a mock-vigilante group that videotapes criminals and turns them over to the police.
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Kill the Man (1999)
The two owners of the Long Shot Copies shop struggle against a copying giant, King Co. Having gotten their start from a one hundred thousand dollar windfall when one of them hit a promotional mid-court basketball shot, they have to find a way to keep their company afloat or fold. Thus starts a series of gimmicks and a war against the opposition, particularly after the...Read all
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The Secret of My Success (1987)
A talented young man can't get an executive position without rising through the ranks, so he comes up with a shortcut, which also benefits his love life.
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Entry Level (2007)
A 38-year old former chef starts all over again when he interviews for entry-level corporate jobs--and can't get one.
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The Disaster Artist (2017)
When Greg Sestero, an aspiring film actor, meets the weird and mysterious Tommy Wiseau in an acting class, they form a unique friendship and travel to Hollywood to make their dreams come true.
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Taking Care of Business (1990)
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
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No Way Jose (2015)
Jose Stern, an erstwhile indie-rocker relegated to playing children's birthday parties, is on the verge of turning 40 and at a crossroads in his life.
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Rocket Singh: Salesman of the Year (2009)
A story of a fresh graduate trying to find a balance between the maddening demands of the 'professional' way, and the way of his heart.
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In the Soup (1992)
New Yorker Adolpho Rollo is your classic head-movie auteur. In his mind, he's creating deathless classics of the screen. Back in the real world, he can't pay the rent on the downtown grothole he calls home.
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Bananas (1971)
When a bumbling New Yorker is dumped by his activist girlfriend, he travels to a tiny Latin American nation and becomes involved in its latest rebellion.
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Flirting with Disaster (1996)
A young man, his wife, and his incompetent case worker travel across country to find his birth parents.
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Free Enterprise (1998)
Two less than successful film producers, approaching mid-life crisis and clinging to their nerdy sci-fi obsessions, suddenly meet their idol: William Shatner.
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Merton of the Movies (1947)
A Kansas bumpkin goes to Hollywood to become a movie star and gets a job burlesquing his favorite actor - only he thinks the role is serious.
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The Last Shift (2020)
Calling it quits after 38 years, an aging fast-food worker trains his young replacement on the graveyard shift at Oscar's Chicken and Fish.
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Fierce Creatures (1997)
Zookeepers struggle to deal with the policies of changing directors.
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