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Before They Were Famous: 5 Surprising Celebrity Career Paths

Headed into a career as a corporate accountant? Why not join the circus, too?

Did you know CNN creator Ted Turner wanted to be a sailor? Or that actor Jimmy Stewart first pursued a career in architecture? Or that Boston Celtics stalwart commentator Tommy Heinsohn is also an accomplished artist? Me neither!

In this Career Start installment Monster rounds up unexpected jobs famous people have, or had, aside from their most recognized career path. Headed into a career as a corporate accountant? Why not join the circus, too?

Tommy Heinsohn

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Now: Boston Celtics color commentator

Before: Celtics player and coach, life insurance, public relations

Most know him as the staunchly loyal color commentator of the Boston Celtics who grumbles about almost every call that doesn’t go his team’s way. Before his time as a reporter, Heinsohn was a player for the Celtics from 1956 to 1965, and also coached the team from 1969 to 1978. He is the only person to have been involved in an official team capacity in each of the Celtics' record 17 championships. If that isn’t loyalty, I don’t know what is.

But wait, there’s more! During his playing years Heinsohn also headed a life insurance company, as well as worked in public relations for Miller Brewing Company. “Over the course of my basketball career, I made more money in the life insurance business than I did playing basketball,” Heinsohn said in a 2014 interview with Comcast SportsNet New England. Who knew?

Wait! There’s even more to his illustrious career. Heinsohn’s a painter, and a successful one at that, with many galleries and exhibitions having displayed his work. “Art is what I’ve been doing since I was a little kid,” Heinsohn said in an interview with WBUR, Boston’s NPR news station. “At times basketball kind of took over my life, so that I wasn’t’ able to really do as much as I would have liked to have done.”

Who says you can’t have it all? Heinsohn proves you can, and then some.


Tony Bennett

Now: 18-time Grammy Award winner singer

Before: Painter

While I’m talking about celebrities who are painters, I might as well mention 18-time Grammy Award winner Tony Bennett. The United Nations has commissioned Anthony Benedetto’s (his full name, which he goes by as a painter) artwork on two occasions and the Smithsonian Institution holds three of his originals as part of their permanent collection.

Whether the man is on stage crooning away, or in his hotel suite painting the nearby ocean, one thing is clearly true: he exudes creativity.


Patrick Dempsey

Now: Actor

Before: Professional juggler, motor racing

It may not have been his full-time job, but before he began his acting career (most commonly known for his role in Grey's Anatomy), Patrick Dempsey was a professional juggler. Really. He managed to place second at the International Jugglers Competition and the Junior Division in 1982 and 1983. Nowadays he juggles acting gigs with motor racing competitions.

Whether behind the camera or the wheel of an Aston Martin, Dempsey proves he has many tricks up his sleeve.


Kanye West

Now: Rapper, singer-songwriter, record producer, fashion designer…

Before: Gap sales assistant

Picture this: You walk into Gap, and there’s Kanye West folding khakis, only you don’t know who he is because it’s pre-rap star Kanye. Did Yeezy aspire to move up the corporate retail ladder? Definitely not. But from sales assistant to self-proclaimed God, someone, somewhere, is bragging to everyone they know that they once bought underwear from Kanye.


J.K. Rowling

Now: Novelist famous for the Harry Potter Series

Before: Secretary

Before young Harry Potter started his fateful education at Hogwarts School of Witchcraft and Wizardry, there was a woman brainstorming his destiny in an Amnesty International office. Working as a secretary, she spent much of her time creating the world of Harry Potter. In Marc Shapiro’s biography on Rowling, she is quoted as saying, “I proved to be the worst secretary ever.” I’m glad she decided to pursue writing instead, too.

So what’s the point of all this silliness? Well, we’ve all got to start somewhere. Just because you’re working a bland job now doesn’t mean you will be doing it forever. With a lot of hard work and determination, you too can find a career doing what you’re passionate about. And maybe even paint a little on the side, too.

Monster Wants to Know: Know of any other interesting celebrity career paths? Share with us in the comment section.

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