For any actor who thinks that the dream will never happen, consider Jon Hamm. The ridiculously handsome leading man who shot to fame as the boozing, womanizing, free-wheeling ad executive Don Draper on AMC’s Mad Men certainly had his share of struggles along the way.

After moving to Los Angeles from St. Louis in a 1986 Toyota Corolla and 150 dollars in his pocket, Jon ended up on his aunt and uncle’s doorstep. But unfortunately, it was thanksgiving and nobody was home. Legend has it the aspiring actor went to an orphan’s dinner for a much-needed Thanksgiving meal.

Hamm spent years waiting tables, teaching, trying his hand at set design, and auditioning.

“I rode the bus and then when I got near where I needed to go, I would rollerblade,” he confessed on the Conan O’Brien Show. “There’s not a worse look in the world than a dude skating down Highland Avenue to an audition to try and sell soap. Roll in sweaty and stinky, skates on–I’m here!”

And even though he had very few credits to his name–certainly not any legitimate credits–Jon came to be repped by none other than the William Morris Talent Agency. He said, “They took me on because they saw a guy a guy who could work.” Such prestigious representation would be a coup for any up-and-coming thespian, but after three years of not winning a single acting job, the poor guy was summarily dropped.

At that point, Jon gave himself a deadline of sorts. If he didn’t make it by the age of thirty, he resolved to quit the business and move on with his life.

“You either suck that up and find another agent or you go home and say you gave it a shot. But that’s the end of that. The last thing I wanted to be out here was one of those actors who’s 45 years old with a tenuous grasp of their own reality and not really working much. So I gave myself five years. I said if I can’t get it going by the time I’m 30, I’m in the wrong place. And as soon as I said that, it’s like I started working right away.”

Indeed, Jon worked steadily for the next ten years, but a genuine breakout role eluded him. However, after years of bit parts and supporting roles, Jon landed the role of troubled mad man Don Draper at the age of thirty six.

According to Wikipedia, “Hamm’s ‘Mad Men’ castmate Eric Ladin had said that one of the reasons he admires Jon is that while he ‘made it’ later than most actors, Hamm never gave up on acting.”

Good thing he kept himself in the game. Jon Hamm went on to win the Golden Globe award in 2008 for best actor in a drama series, and is currently working on three films: Nostalgia, High Wire Act, and Libby and Malcolm. That’s a pretty busy schedule for someone who once got his car repossessed because he couldn’t pay his many parking tickets.