The Humbling First Jobs of 25 Very Successful Celebrities and Business Leaders

Updated: June 17, 2009

You may covet their fame and fortune now, but back in the day, you would never have wanted to trade places with some celebrities and business leaders. Many of the rich and famous had to work horrible jobs for chump change — we're talking pumping gas and cleaning girls' locker rooms — before making it big.

Donald Trump:

Trump, now a filthy-rich real-estate investor and host of the hit NBC show "The Apprentice," got his start collecting soda bottles for the deposit money. Later, he went around with rent collectors to see how that business worked.

Michael Dell:

The founder and CEO of Dell washed dishes at a Chinese restaurant before starting his namesake computer company.

Johnny Depp:

As a youngster, Depp donned makeup for his gig in a KISS tribute band and also dressed up as part of the faux B-52s, as well as Iggy Pop. Back then, Depp pocketed about $25 on bad nights; now he makes about $25 million per year.


Walt Disney:

Before he dominated the cartoon and amusement-park empire, Walt Disney worked as an ambulance driver in France during World War I. He took the gig after he was rejected from the Army for being underage.


Jim Carrey:

Before he had people in stitches, this funny guy worked as a janitor mopping floors at a tire factory. He took the job at age 15 after his father became unemployed. Carrey also had a another job as a security guard. The comedian credits his early lessons in strife and toil for instilling his love of comedy: He visited local comedy clubs to relieve stress.

Suze Orman:

Today, she tells people how to spend their money, but during her early years, Orman bussed tables to make a buck. The personal-finance guru, who barely made it to college, also washed dishes.

Clint Eastwood:

This ruggedly handsome actor, director and businessman started out as a pool boy. He later worked as a gas-station attendant and a firefighter. Eastwood also played ragtime piano at a bar in Oakland, Calif.

50 Cent:

The multiplatinum-record-selling American rapper began his working life selling drugs in Queens, N.Y. The rapper says that the hard life taught him how to manage his music empire in areas such as dealing with distributors and marketing new products to customers.

Quentin Tarantino:

This filmmaker, known for flicks such as "Kill Bill" and "Reservoir Dogs," was an usher at an adult movie theater in Southern California. Despite the job's sleaziness, Tarantino once told Charlie Rose, "To me, the greatest job a person could ever have was being an usher at a movie theater, you know. You get to go to a movie theater all day long, and then you get to see all the movies for free." Tarantino later worked as a video-store clerk.

Chris Rock:

This comic started his career as a busboy at a Red Lobster franchise in Queens, N.Y. Always on the lookout for material, Rock recalled his experience in a skit on "The Tonight Show with Jay Leno" in 2003. Rock quipped, "The thing about Red Lobster is that if you work there, you can't afford to eat there. You're making minimum wage. A shrimp costs minimum wage." Rock then bussed tables at Comic Strip Live in Manhattan and was allowed to try out his own jokes on stage.

Jennifer Aniston: Aniston's beginnings entailed far worse than donning too few pieces of flair: She was both a telemarketer and a waitress before hitting it big as Rachel on "Friends."

Lucille Ball: Always a goofball, Lucille Ball was reportedly fired from an ice-cream shop for not remembering to add bananas to banana splits.

Warren Beatty: Before he exploded onto the movie scene in 1961's "Splendor in the Grass," Beatty reportedly worked as a rat catcher.

Marlon Brando: Talk about a dull job: The Godfather became a ditchdigger after he was expelled from military school.

Michael Douglas: The New Jersey-born actor really did live the blue-collar life for a hot minute when he got his first job as a gas-station attendant.

Tom Hanks: This everyman actor started out as a popcorn and peanuts vendor at the Oakland Coliseum in California and once worked as a hotel bellhop carrying bags for a number of stars.

Stephen King: Solitary work can inspire writers, and Stephen King found his spark when he worked as a janitor. King's experience cleaning the girls' locker room helped inspire his novel "Carrie." He also worked at a mill bagging loose fabric, as well as at a laundromat.

Madonna: This successful singer and actress worked at Dunkin' Donuts as a teenager. She later went on to dance and model to pay the rent before she bounded onto the music scene in the early 80s. Today, Madonna ranks as the 21st richest celebrity in the world.

Brad Pitt: When he was a struggling young actor, Pitt drove limos, moved refrigerators and dressed as a giant chicken for a Mexican restaurant. Pitt is currently the 10th highest paid celebrity in the world.

Julia Roberts: Before she became famous, Roberts worked in an ice-cream shop.

Steven Spielberg: Spielberg used to work outside keeping the bugs away from fruit trees. Today, Forbes magazine estimates his worth at $3 billion. A few years ago, LIFE magazine named Spielberg the most influential person of his generation.

Robin Williams: Robin Williams worked as a street mime and in an ice-cream shop before he got into acting.

George Steinbrenner: The principal owner of the New York Yankees since 1973, Steinbrenner's first "job" was helping his siblings raise the family's chickens — for a few dollars a week. He sold the eggs to neighbors in his small hometown of Bay Village, Ohio. He even killed and dressed chickens for folks who wanted a fresh one.

Mariah Carey: This beauty-school dropout turned music diva was fired from her job as a hat checker. Today, she's one of the most successful female vocalists of all time and boasts the most No. 1 singles for a solo artist in the United States.

Rachael Ray: The face of this cooking-show hostess, television personality and author is everywhere these days, but it used to be stuck behind the candy counter at Macy's in New York City. The job wasn't a complete bust, however, as Ray eventually managed the fresh-foods department, which helped pave her way to her TV cooking career. Today, Ray is worth tens of millions of dollars.

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