5 Unexpected Jobs Famous Folks Had Pre-Fame

Life didn't start out all rosy for some of these celebrities. Here are some of the most famous people who did unexpected jobs before they were famous.

In the journey of life, not all our favorite celebs had it easy. There are many famous people who did unexpected jobs to survive and push their careers.

Sure, some got it right from the initial stage. Take former-president Barack Obama, who, working backward from the presidency, served at the federal congressional level, preceded by the state level, preceded by the local level, preceded by a successful law background. Or take actors like Drew Barrymore who have been on the silver screen since they were children.

Other times, the folks we celebrate as celebrities or admire for their political, humanitarian or business success – or, for that matter, those who we loathe for the harm they have done – end up in their notable positions after time spent on markedly different life paths.

Here are five famous people who did unexpected jobs before they were famous:

5. President Harry Truman

Harry Truman - The 33rd president of the United states did a number of unexpectd jobs before getting into the oval office

Famous Biographies

One of the famous people who did unexpected jobs before they got famous was President Harry Truman.

Truman was the 33rd president of the United States of America following the death of Theodore Roosevelt in 1945. He was president from 1945-1953.

However, before he became famous as president, Harry Truman worked some unexpected jobs as a teenager. Due to his family’s financial troubles, Truman had to drop out of school and later took a job in the mailroom of a Kansas mailing outfit. After leaving the mailing company, he went on to work as a bank clerk and a construction worker.

Later, in 1906, he left his job as a bank clerk to work on his family farm, where he worked for almost a decade. When his father died in 1914, Truman was devastated by the death and left the farm business to other members of the family while he went out to find another job.

It was during this period that he founded a small mining company and became a partner in an oil company, none of which brought him any financial returns or relief.

President Harry Truman, before OKing the only-ever hostile usage of nuclear weapons, was at one point in debt up to his eyeballs after his clothing business failed. In fact, Truman’s business failed so colossally, he was paying off the failure for almost a decade and a half.

His business life did manage to vault him into political life, though, and we assume that by the time he had his finger on The Button, any creditors still awaiting payment decided to fall silent.

4. Musician Elvis Costello

Elvis Costello - The Famous singer served as a bank clerk in his unexpected job before the stardom

Ultimate Classic Rock

Yeah, Elvis Costello is among the famous people who did unexpected jobs before their fame.

Musical Renaissance man Elvis Costello worked a number of office jobs, including at a bank and as a clerk for the cosmetics firm Vanity Fair. Costello took the step of reliving his first “career” through his second, singing about the experiences he had as a frustrated young man in the song titled (ironically, of course) “I’m Not Angry.”

If you listen to the lyrics, you will start to think “Hey, y’know what? He WAS angry.”

3.) President Bashar al-Assad

Bashar Al Assad - The Syrian president is another famous person who did unexpected jobs before becoming the rule of Syria

Al Jazeera

The controversial figure who is president of Syria is another famous person who did unexpected jobs before becoming president.

Bashar al-Assad is today known as a murderous thug responsible for the deaths of tens of thousands of Syrians, the very countrymen he should be serving and protecting as their (no longer legitimate) president. But instead of studying at Ruthless Despot Academy, Assad studied to be… an optometrist.

When one’s father has ruled a country as a de facto dictator for 29 years, and when you have an older brother groomed for office, I suppose that’s what you do: You study ocular medicine.

But when Assad’s brother was killed in a car accident and Assad Senior kicked the bucket, little Bashar assumed power, and he has kept it for over a decade now thanks to what are laughably called elections. Except that you don’t laugh openly about these things if you are in Syria these days, what with the death and horror.

2. Actor Pee-Wee Herman

Pee-wee herman was one the famous who did unexpected jobs - Herman was a door to door salesman


Another person on the list of famous people who did unexpected jobs before fame struck was this man.

Pee-Wee Herman, before he was Pee-Wee and was still just Paul Reubens, worked in various restaurants (in the kitchens, scrubbing and such, to be clear) and then as a salesman for the Fuller Brush Company, a company that, as you might have guessed, sells various brushes.

Just picture Pee-Wee showing up at your door in character… Would that help sales or hurt? I’m going to guess the latter. This is an example of a stopgap career, though, as he was working on his acting and comedy the whole time.

1. Celebrity Madonna

Madonna - The Pop Queen worked in the Dunkin Donuts and other places before the fame


In order to keep body and soul together along with her career, Madonna was one of the famous people who did unexpected jobs after she dropped out of the University of Michigan.

Her other “career” was brief, but it’s just so hilariously improbable that we can’t help but share it: Madonna worked briefly as a waitress at a Dunkin’ Donuts in NYC. Now, we know what you’re thinking: “Dunkin’ Donuts has waitresses?” Well, apparently some do – we’ve cross-referenced this fact and it is true: The Material Girl was, at one point in the late ’70s, decidedly more glaze than glitter.

However, there are reports that she got fired from the job because of her temper, as she was reported to have hosed down a surprised customer with donut jelly.

Prior to that, another of the unexpected jobs Madonna did before fame was posing nude for art classes, and she also spent time as a waitress at the restaurant known as the Russian Tea Room.

So take heart, dear readers: You may not be stuck as the CEO of a successful Fortune 500-ranked business or as a prolific poet forever – you, too, could go on to have a celebrated second career! Or you could invest in soybeans and hope the market goes haywire — we don’t know — you’ll figure something out!