See This Guy: Sylvester Stallone


What if you had a dream that just wasn’t coming true? Would you keep fighting?

Sylvester Stallone had to fight from the beginning. Literally.

While his mother was delivering him, a careless medic severed the facial nerves in his lips, eyelid, tongue and chin, which led to permanent deformity (to be seen in his now-famous sneer and slurred speech).

As a kid, he was bullied constantly. His family couldn’t afford a weight set, so he got creative, using cinderblocks and old car parts to build his body.

His parents’ hostile relationship also took an emotional toll on him. And after their divorce, he spent years in foster care.

That tough spirit didn’t lend itself well to academia, as Sylvester was expelled from 14 different schools. When you have a habit of lighting fires, shooting arrows out windows and stealing the nuns’ crucifixes, you’re probably not hanging around too long to get to know your classmates.

Stallone eventually graduated from a high school for troubled youth and later enrolled at the University of Miami – where he dropped out to pursue an acting career in New York City.

To say he struggled for years would be a mild understatement. He literally went on thousands of casting calls but couldn’t find enough work to survive. 

He took a long string of odd jobs to make pocket money, including hairdresser (!), cleaning out the lion’s cages at the Central Park Zoo and as a cinema usher, where he scalped tickets on the side for extra cash. He was fired when he unknowingly tried to sell tickets to the theatre owner.

A particular low point: after being evicted from his apartment, he had to sleep at the Port Authority Bus Terminal for three weeks. He was so desperate, he took a role in a porn flick because in his words "it was either do that movie or rob someone. I was at the end – the very end – of my rope".

A move to Hollywood landed him some small roles, but he was typecast as a thug. He turned to writing as a way to pass the time while waiting for his big acting break.

One script – about a down-and-out fighter with a ton of heart – caught the attention of some heavyweight producers. And in a legendary display of nerve, Stallone turned down $350,000 for the script when he was told he couldn’t star in it – despite only having $100 to his name and a pregnant wife. He held firm, got the acting job and took far less money.

Rocky became an international sensation, nominated for ten Oscars and becoming one of the highest-grossing films of all time.

Stallone is the only actor to open a number one film across five decades. He is a real-life Rocky Balboa.

Not bad for a guy who “looked funny and talked funny”.



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John Lavallo57 Posts

John is Columbia Business School MBA with expertise in marketing, business leadership, and law. John is a successful entrepreneur who took his first company public. He currently resides in New York City.