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Movies & Shakers (Part 1) 20 Comedies About Startups

As most entrepreneurs know, it’s good to smile at one’s successes and even better to laugh at one’s failures (erh, lessons) as this list of films featuring inventive business pros shows.
20. Chitty Chitty Bang Bang (1968) 
A singing inventor (Dick Van Dyke) creates a flying car that helps him find true love and save the country in this fantasy adventure from the minds of Ian Flemming and Roald Dahl. 
19. Bridesmaids (2011)
After losing her Cake Baby bakery, Annie (Kristen Wiig) gets some sugar from road cop Rhodes (Chris O'Dowd), not to mention a spicy Mexican lunch.
18. How to Succeed in Business Without Really Trying (1967) 
Before he became a CEO on Mad Men, Robert Morse played a window-washer who hits the glass ceiling of the Worldwide Wicket Company. 
17. Baby Boom (1987) 
When a no-nonsense businesswoman (Diane Keaton) reluctantly inherits a toddler, she brings big business to a little country town when she builds a baby food empire.
16. The Guilt Trip (2012)
Andy Brewster (Seth Rogen) hits the road (and the wall) with his mother (Barbra Streisand) on a quest to get his organic cleaning product ScioClean into a major retail store.
15. High Fidelity (2000)
Aimless hipster Rob (John Cusack) runs the record store Championship Vinyl (where some of its few customers are run out) until he starts to grow up and starts his own record label, Top 5 Records.
14. The Main Event (1979)
When Hillary Kramer (Barbra Streisand) is swindled out of her successful perfume business and is left with nothing but a faux boxer (Ryan O'Neal), she turns this miss of a fighter into a hit.
13. Ghostbusters (1984)
Writers Dan Aykroyd and Harold Ramis play the title characters alongside Bill Murray who form a ghost-catching startup to combat the supernatural happenings starting up in New York.
12. The Jerk (1979)
Despite his humble beginning as a “a poor black child,” Navin Johnson (Steve Martin) develops the Opti-Grab to keep people's glasses from sliding down their noses.
11. Big Night (1996)
The fate of a struggling restaurant rests on one meal prepared by its owners—Italian immigrant brothers (Stanley Tucci and Tony Shalhoub)—who dish out subtle humor in this 1950s-set indie gem.
10. Paper Moon  (1973)
A father and daughter (Ryan and Tatum O’Neal) have a unique way of finding customers for their Bible business in this Great Depression-set story.
9. Edward Scissorhands (1991)
A stranger to suburbia (Johnny Depp) makes lemons out of lemonade by working with what he’s got (namely scissors for hands) to help start a hair salon and successfully prune shrubs—despite being paid in cookies.
8. Napoleon Dynamite (2004)
While Napoleon's uncle Rico (Jon Gries) peddles breast-enhancement products as well as plastic bowls with the help of brother Kip (Aaron Ruell), Deb shows the true entrepreneurial spirit—selling handmade bracelets and starting up her own company Glamour Shots by Deb.
7. Step Brothers (2008)
After undergoing a series of comic trials via their unsuccessful job search, it looks like middle-aged children (Will Ferrell and John C. Reilly) will finally get to move out of their parents’ home when they start up a successful karaoke company.
6. The Producers (1968)
Mel Brooks makes light of the theatrical world with this dark comedy that relays how to guarantee success on Broadway.
5. Jerry Maguire (1996)
This Cameron Crowe classic features Tom Cruise, Renee Zellweger, Cuba Gooding, Jr. and recognizable lines such as, “You had me at hello,” and “Show me the money!”—phrases every entrepreneur longs to hear.
4. Lover Come Back (1961)
Hailed as Best Comedy Picture and Best Comedy Actress (Doris Day) at the Laurel Awards, this often overlooked film about an advertising executive (Rock Hudson) who creates a campaign for a product which has not been invented features the devilishly clever Oscar-nominated screenplay by Stanley Shapiro and Paul Henning.
3. Willy Wonka & the Chocolate Factory (1971)
After inventing the Everlasting Gobstopperfizzy lifting drinks, and lickable wallpaper, it’s only natural that a tycoon as original as Wonka (Gene Wilder) would run an equally creative campaign to hire his successor.
2. Being John Malkovich (1999)
When unemployed puppeteer Craig (John Cusack) finds a portal into John Malkovich’s head, he begins selling a piece of his mind for $200 a pop.
1. Romy and Michele's High School Reunion (1997)
In an effort to impress their former school mates, Romy (Mira Sorvino) and Michele (Lisa Kudrow) pretend they invented Post-it-notes. Their story doesn’t fly, but nerd-turned-businessman Sandy Frink (Alan Cumming) does when he arrives in a helicopter, having made billions with his rubber invention. But he’s not the only school success story: outcast Heather Mooney (Janeane Garofalo) invented Lady Fair Cigarettes ("twice the taste in half the time for the gal on the go"). And popular Lisa Luder (Elaine Hendrix) became an editor at Vogue—a position that enables her to identify Romy and Michelle’s real gift: they’re great clothing designers! With her stamp of approval and a loan from Sandy, Romy and Michelle open up a successful boutique where Heather can now shop.

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