Jon Hamm Talks Meeting Tom Cruise, Working on Softcore Porn Sets, and Landing ‘Mad Men’

It’s shaping up to be an astounding year for award-winning sex symbol and Hollywood icon Jon Hamm, who joined the Stern Show for the first time Monday morning to promote his new crime comedy “Confess, Fletch” and speak with Howard about everything from which “Real Housewives” cast reeled him in to whether the rumors were true he preferred “going commando” on set. In recent months, Hamm has co-starred in Tom Cruise’s billion-dollar “Top Gun” sequel, reprised his role as the angel Gabriel on Armageddon adaptation “Good Omens,” joined Jennifer Aniston’s award-winning drama “The Morning Show,” and taken over for Chevy Chase in the “Fletch” franchise. Between his latest string of hits, his office full of awards, and the fact paparazzi hides behind bushes to snap photos of him running errands, one could be forgiven for assuming Hamm’s show business successes were preordained from up on high. But as the 51-year-old acting teacher turned “Mad Men” megastar told Howard, his journey to the top was anything but guaranteed.

“I ended up going on a million auditions and not getting any of them,” Jon said, adding, “I auditioned for big movies and big TV shows and all of these things, and I still to this day joke with Jon Favreau that he beat me out for a part in ‘Deep Impact.’”

It Took a Village

Born in St. Louis to parents who divorced when he was just two, Jon was raised at first by his mom. She didn’t have much money, but she was loving, supporting, and instilled in him the value of a quality education. Tragically, colon cancer took her life when Jon was only ten.

“I loved my mom, and I loved my life … I knew that I was loved and taken care of and that that was never going to go away — until it did,” Hamm told Howard.

“I’m still unpacking it,” he continued. “It’s a wound. It’s a trauma. It’s a serious thing that, if you ignore it, only gets, you know, more tangled up and becomes this real object blockage, really, in your emotional life and your real life.”

It didn’t help Jon next had to live with his dad, who was emotionally unequipped to provide him the support he needed. “He didn’t have the tools — I don’t blame him for it,” Jon said. “Do I wish that there was somebody in my life at that point that was able to ease that pain? For sure, because I’m still dealing with it.”

Jon had plenty of fond childhood memories but told Howard he deeply regretted never getting an opportunity to have adult conversations with his mother and father, who himself passed away about a decade later. “It’s a bummer and it’s unchangeable. You can’t rewrite it and you can’t go back into the past,” Jon said. “I really wish I could have asked my dad a million different things. I really wish I could have asked my mom a million different things.”

Thankfully, Jon was still surrounded by people who cared for and supported him, from teachers to parents of friends. “It’s why I believe in community. Nobody gets through this by themselves,” he said.

Jon attended John Burroughs School, the suburban prep school his mother had hoped he would attend, and played on both the football and baseball teams, which he said gave him a sense of belonging. He eventually went off to college but didn’t stay away for long, returning to John Burroughs after accepting a job teaching acting to eighth graders.

“That was really fun, and I really enjoyed it,” he said. “I had a lot of great kids and students.”

Crashing Bar Mitzvahs With Paul Rudd and Joe Buck

At 25, Jon quit teaching and drove his overheating Toyota Corolla out West to give acting a serious go. He didn’t have much money and he didn’t have any leads on a job, but he did have an in with a rising star.

“The one person that I knew who had a Hollywood career was Paul Rudd, who I knew from back in the Midwest,” Jon said, explaining they’d become friends back in the late ‘80s when Rudd rocked “long Michael Hutchence hair” and a “Duran Duran jacket.” “He was everything that you thought the cool guy from college looks like in 1988.”

Hamm recalled many nights out on the town with Rudd and soon-to-be-famous broadcaster Joe Buck, who also hailed from the Midwest, including one in which Buck and Hamm crashed a bat mitzvah where Rudd, who had a side job as a party D.J., had been working. “We were jealous of having that job. That was a good-paying gig,” Hamm laughed, adding, “There’s some 47-year-old woman who had at her [bat mitzvah] Paul Rudd, Joe Buck, and Jon Hamm, and was blissfully unaware of all of it.”

Rudd did more than just invite Hamm to his gigs. The actor, who’d just starred in “Clueless,” also put Jon in touch with someone who helped him find representation.

Hard Times and Soft Porn

Making ends meet while trying to kickstart his acting career was tough. He worked odd jobs, waiting tables and dressing sets on softcore porn films, and took theater roles when he could find them.

At 25, Jon had vowed to carve out an acting career by 30 or else he’d return home and resume teaching. He went on countless movie and TV auditions over the next five years but couldn’t book anything of substance. Then in 2000, at the age of 29, he landed a small part as a Zorro-clad bartender on the NBC drama “Providence.”

“I was over the moon. It was basically one day of work, but it was more money than I’d probably made a couple years up to that,” he said.

It didn’t take long for the network to invite him for another visit to the set. “They said, ‘They might want to bring you back.’ I was like, ‘Oh, because I didn’t do a good job and I have to like redo it?’ … They said, ‘No, another episode,’” he recounted, explaining the network offered him a six-episode deal that put his career on an entirely new path.

Learning to Let Go on “Saturday Night Live”

Hamm has hosted “Saturday Night Live” and made special guest appearances several times over the years, and while his visits to Studio 8H were all well received, Howard couldn’t help but wonder if it was hard for the star of a scripted, closed-set drama to come onto “SNL” and be expected to read from cue cards while performing live in front of millions.

Hamm copped to being plenty nervous in 2008 before hosting his first episode – which turned out to be an especially tumultuous one because star cast member Amy Poehler had just gone into labor. “I get a knock on the door … [It was] basically, ‘We’re changing the show.’” Jon told Howard. “I was like, ‘Oh, ok? In six hours, right? Great. Where do I need to go?’ [They were] like, ‘Don’t worry about it.’”

Well, he worried about it.

At least right up until he had an epiphany amid a sea of chaos just before delivering the opening monologue. “The stage manager is screaming, Don Pardo is reading your name – I don’t know what happened, but I realized in that moment that ‘Oh, this is a roller coaster. I have to just not fall out of the roller coaster, and I’ll be fine … I’ll just enjoy the ride. This is what it’s supposed to be,’” he said, explaining that after that he started having a great time. “I was like, ‘Oh right. Enjoy this. Enjoy the insanity. Enjoy the chaos.’”

Hamm also remembered an invaluable tip he got from another famous “SNL” alum – Jason Bateman. “Just go and be their guest. You’re their guest. You’re going to their home,” Jon recalled the actor saying. “They’ve been doing this for 40-some-odd years. They know how to do it. You’re not going to tell them something they don’t know.”

Auditioning 7 Times for ‘Mad Men’

AMC famously put Jon through seven auditions before awarding him the role of Don Draper on “Mad Men.” The process was a bit more grueling than Jon is used to now since he was far from a household name at the time, but he was more than willing to jump through all those hoops if it meant he’d have a chance to star on the series.

“I remember reading the script, putting it down, and thinking, ‘Holy shit, that’s a really good story,’” he said.

The first audition was held at an ad agency in Santa Monica. Hamm vividly recalled driving across town in the rain to get there. “It took me about two hours to get to this audition where I’m sitting next to like a 15-year-old kid, waiting,” he told Howard. “The kid goes, ‘Are you here for the toothpaste commercial?’ And I go, ‘What? No.’ Then I thought, ‘Maybe I can get a job on that toothpaste commercial … I got decent teeth … Maybe I can double-dip on this.’”

To win the part, Hamm ultimately overcame a wide range of competition. “The only name that I remember from any of those [audition] sign-in sheets … was Josh Malina, who I’m not sure had a great shot at being Don Draper. But it would’ve been a choice,” Hamm laughed. “And I love Josh. He’s a great, wonderful actor.”

Breaking Mad With Bryan Cranston

“Mad Men” racked up over 100 Emmy nominations over seven critically adored seasons. As luck would have it, however, the show’s run coincided with that of another celebrated show: “Breaking Bad.” Though Hamm finally did take home the statue for Outstanding Lead Actor in a Drama Series in 2015, it was only after Bryan Cranston’s “Breaking Bad” had concluded. Howard imagined constantly facing off against one of the most beloved series of all time was frustrating.

“Had I never won for that role I think it would’ve hurt a lot more, but [I did win],” Jon laughed. “And I thank Bryan every day for kindly bowing out … so I could come in at the end.”

Hamm considers Cranston a dear friend and sees parallels between their careers. “He, a lot like me, was kind of a journeyman guy for a long time [before] finally getting this kind of career-defining role. He has made the most of it. He’s one of the mensch-iest guys you’ll ever meet,” he told Howard.

While Cranston won more Emmys for “Breaking Bad,” Hamm did recall one joint AMC photoshoot where he held the upper hand. “I’m in this suit with a cigarette, a tie, and the hair slicked back, and Bryan is in his tighty-whities, desert boots, and a chemistry apron with safety goggles,” Jon told Howard. “He walks out … and looks at me and goes, ‘I feel like I got the wrong end of this deal.’”

Love, Marriage, and Breathable Cotton

Having been fascinated for years at the longstanding rumors that Hamm is well-endowed and doesn’t wear underwear, Howard naturally questioned the actor about any validity to the rumors. “Did you bring it, first of all?” co-host Robin Quivers jokingly asked Hamm.

“I have worn underwear every single day of my life, who doesn’t wear underwear?” Jon said of rumors to the contrary, including a legend that he once was told he couldn’t go commando on the set of “Mad Men.” “I love a comfy boxer brief … I like a breathable cotton.”

Hamm, considered a sex symbol throughout his career, was also quick to downplay his supposed good looks, insisting they didn’t drive him to a career in front of the camera. “My growing up … was more about kind of fitting in and achieving and hopefully being good at whatever it was that was in front of me, whether it was school or sports … By the time I got to pursuing acting really in a real way, I was in college, and I ended up getting a scholarship to do it and it was literally just something like ‘I think I’m good at this,’” he said of his early days. “Being good-looking or what have you is obviously so subjective too … somebody’s great-looking guy …  another [person] doesn’t give a second look so I never really had a sense of that.”

The actor, who has gone to psychotherapy for quite some time, appeared keener on discussing how the work he’s done has positively impacted his love life. “I’m in a relationship right now … and it’s comfortable. It’s a feeling of taking care of someone else and being taken care of, and it’s also been a process of working on myself, my mental health … and unpacking all of that trauma, my realizing that, you know, when you lose somebody that’s so important to you like a mother so early, that creates a wound that blocks a lot of that emotional accessibility, that blocks a lot of that availability, and vulnerability,” he revealed, referencing his relationship with actress Anna Osceola, whom he first met on the set of “Mad Men.” “It’s only been in the last couple of years of me kind of sitting down and really thinking about it … that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness — all that stuff that sounds hokey and whatever but it’s real and … it’s what I’m working for.”

Tom Cruise, Mom Cruise, and ‘Top Gun 2’

Hamm felt fortunate to star alongside Tom Cruise in “Top Gun: Maverick,” the smash-hit sequel to one of Jon’s favorite films a teenager. While the two A-listers enjoyed several scenes together on-screen, he told Howard his first meeting with Tom occurred many years earlier at a football party thrown by late-night host and Stern Show celebrity superfan Jimmy Kimmel.

Jon distinctly recalled a rumor going around that day that Cruise might stop by. “I was like, ‘No, he’s not. What are you talking about? That’s like saying Santa Claus is coming,’” he recalled.

However, the doorbell soon rang and there stood Tom Cruise and his mother. “We got Tom Cruise and Mom Cruise, and we’re all having an out-of-body experience,” Hamm recalled, explaining the situation got even more surreal after Tom told Jon he was a big “Mad Men” fan. “He was very direct and intense, [saying] ‘I love that show,’” Jon continued. “That was a good day – a really good day.”

Their story picked up over a decade later when Jon’s agent called him and said he’d been asked to enlist in the long-rumored “Top Gun” sequel.

“I was like, ‘Well, then, the answer is yes … If this goes away, you’re all fired,’” Hamm recalled with a laugh, describing the decision as a “no brainer.” “The answer [was] ‘yes, and I’m sure it will be a big hit’ — and it was,” he added.

“Confess, Fletch” is out now in theaters and on demand.