While Jon Hamm became best known for his role as the dapper Don Draper on period drama Mad Men, the actor had been struggling to make it big many years before that.

Now 48, he was 36 at the time that he snagged what would be the biggest role of his career. At that age, one could say that Hamm got a late start in the business. Sure, he had acted before that. But Mad Men was the role that finally put him on the map and made Hamm a household name. He has since appeared in a number of films as well as popular series.

But his path to stardom is an interesting one, paved with heartache, love, passion for the craft, and even an arrest in his younger days.

Here are a few interesting facts you won’t believe about the classically handsome actor.

He Has Never Been Married

It’s hard to imagine that a man as famous as Hamm has never been married. But he hasn’t. He was technically common-law married, in a long-term relationship with fellow actor Jennifer Westfeldt for almost 20 years from 1997 through to 2015.

But the pair never tied the knot, both agreeing that they didn’t need a piece of paper to confirm their relationship, with Hamm being quoted as saying that he believes people only need to get married when they’re ready to have kids. He hasn’t been publicly linked to anyone romantically since then.

He Was Ellie Kemper’s Drama Teacher

After graduating from the University of Missouri with a Bachelor of Arts in English, Hamm went back to his old high school to teach acting to eighth graders. One of his students was Ellie Kemper who, of course, went on to become a successful actor herself.

Interestingly, Kemper starred in Netflix series Unbreakable Kimmy Schmidt about a woman who was abducted as a child and kept in an underground bunker for 20 years with three other women. Hamm had a guest role in the series as the crazed man who kidnapped her.

He Only Has One Emmy

The audience was on their feet to cheer for Hamm when he finally won an Emmy Award after being nominated a total of eight times for the role. He won in 2015, his last year of eligibility before the series was finished.

Hamm has also received several other Emmy nominations, including multiple ones for his guest role on 30 Rock as well as for his guest role on Unbreakable Kimmy Schmidt. With plenty of new roles coming up, chances are Hamm will get to take home another one sometime soon.

His Parents Died When He Was Young

Hamm’s parents divorced when he was just two years old. His father managed a family trucking company and his mother was a secretary, suggesting that he had a pretty typical middle-class upbringing.

Hamm sadly lost his mother when he was only 10 years old after she passed away from colon cancer. He went on to live with his father and grandmother in Missouri. His father, however, passed away a decade later when Hamm was just a young man of 20.

He Was Arrested for Participating In a Violent Hazing in University

Yes, the seemingly squeaky-clean Hamm had a wild side when he was younger. In 1990, while at the University of Texas, he participated in a violent hazing incident as a member of the Upsilon chapter of the Sigma Nu fraternity. A man was being beaten by a paddle and a broom and Hamm led him around the fraternity house with a hammer claw around his testicles. They also reportedly set the poor boy’s clothes on fire.

Not surprisingly, the fraternity was shut down following the incident. Hamm was sentenced to probation but the charges were dismissed five years later.

He Moved To L.A. With $150 In His Pocket

As if straight from a cliched story about a starry-eyed aspiring actor, Hamm really did head to Los Angeles with just a few bucks in his pocket and a dream. He found the idea of having a normal career wasn’t for him so he moved to L.A. in 1995 with just his car and $150.

Again, much like how many other actors got their start, he lived with three other aspiring actors and worked as, you guessed it, a waiter while booking auditions. He worked in theater as well but was eventually dropped by his agency in 1998 because he wasn’t booking any gigs. Ouch.

He Worked On A Softcore Porn Movie

Before you get worked up, or think the wrong thing, no, Hamm he was not working on camera in such a film. However, he did work a short stint as a set designer on a softcore porn movie.

Hey, every actor has one job they might be embarrassed to admit, or that might turn heads, whether it’s a foreign commercial with them dancing and singing, a role in a terrible B-movie, or, in Hamm’s case, his one link to the porn industry. He likely can look back on it today, however, and laugh. It was a job and it paid the bills.

Matthew Weiner Thought He Was Too Handsome to Play Don Draper

Yes, there is such a thing as being “too handsome” for a role and this is the feedback Hamm got when he auditioned to play Don Draper. Matthew Weiner, who created the show, was reluctant to hire him because of his classic good looks. But in the end, he decided that it made sense to make Don a perfect specimen on the outside while being tortured on the inside.

Hamm’s own backstory also helped convince Weiner to give him the part. Weiner felt that the fact Hamm had his own share of struggles in life, including his parents’ early divorce and the death of both of his parents at a young age, was something he could draw on for the role. Indeed, Hamm says he used memories of his own father to help him portray Draper’s inner torment.

He Dated Jennifer Westfeldt For Almost 20 Years

As noted above, Hamm and Jennifer Westfeldt, who is known for her role in Wonderful Town, for which she was nominated for a Tony Award, and as a screenwriter who wrote the independent film Kissing Jessica Stein, dated for close to two decades, from 1997 to 2015.

They lived together in their joint homes in the Upper West Side in New York City as well as Los Angeles. Ultimately, it didn’t work out and they ended their relationship right as Mad Men was ending its run.

He Doesn’t Actually Smoke

Don Draper was a heavy smoker. It was rare to ever see him without a cigarette or drink in his hand, often both. But like many others on the popular AMC series, Hamm didn’t actually smoke. Instead, he would smoke herbal cigarettes while filming.

He did smoke when he was younger, but quit at the age of 24, and has reportedly been tobacco-free since. So while, as Don Draper, he worked on ad campaigns for cigarettes and partook in them often, Hamm is tobacco-free in his real life.