While he had a role in the megahit Top Gun: Maverick, Hamm said on Monday's Howard Stern Show that he actually met the superstar a decade earlier at a kegger at Jimmy Kimmel's house.
Hamm said Kimmel was known for throwing all-day football viewing parties with big groups of people. "They'd have a keg and he'd make pizzas," he said. "It was L.A. so it's sunny and games start at 10 in the morning."
Early on at this party — attended by actors, comedy writers and comics — a rumor swirled that Cruise was going to be in attendance. Hamm recalled being doubtful: "No he's not. What are you talking about? That's like saying Santa Claus coming. There's no way and you're an idiot if you believe that. And Jimmy, famously, is a very big prankster."
The doorbell soon rang and none other than Cruise rolled in — and he wasn't alone.
"It's not a Tom Cruise impersonator, it is Tom Cruise — with his mom," Hamm said, referring to Mary Lee South, who died in 2017. "So we got Tom Cruise and Mom Cruise and we're all having an out-of-body experience. Arguably the most famous person on the planet is in this living room watching nine football games at once [with us]."
On top of it, Cruise turned out to be a big fan of Hamm's work in Mad Men, which ran from 2007 to 2015.
"He was like — in a very Tom Cruise way, very direct and intense — 'I love that show. I love that show,'" he recalled. "'Thanks man.' Holy cow. That was a good day."
Fast-forward 10 years when Hamm was driving and got a call from his agent that Cruise wanted him for the Top Gun sequel. He said yes on the spot — even though the finances hadn't been worked out.
"'The answer is yes. If this goes away, you're all fired,'" he recalled telling his agent with a laugh. He called it a "no brainer" to say yes — not just because he was offered the role on the spot, but because he loved the original and he'd get to work with Cruise. "The answer is yes, I'm sure it will be a big hit" he recalled saying, "and it was."
It's been a few years since his Emmy-winning run as Don Draper in Mad Man. He went on to clear up a long-running rumor, going back nearly a decade, about whether he wore underwear for his role playing the '60s ad man. There were rumors show brass had to tell him to put on underwear because he had been revealing too much below his waist by going commando. For years, Hamm made it clear he wasn't having a public conversation about his private parts — and typically in an impatient and unamused way.
When Stern asked about "the most famous rumor" about Hamm — "the whole penis thing" — Hamm laughed along — because of course Stern was going to ask.
"The whole penis thing," Hamm laughed at the question. He finally answered, "I have worn underwear every single day of my life, Howard. First of all: Who doesn't wear underwear?! I wear underwear... I love a comfy boxer brief. Thank you very much. I like a breathable cotton. Come on man, who doesn't?"
Hamm also talked about about being in a relationship with Anna Osceola, who appeared in the Mad Men series finale. He said, after doing a lot of therapy in recent years, processing early loss and grief in his life, he has could see himself getting married some day.
"I'm in a relationship right now ... and it's comfortable," he said. "It's a feeling of taking care of someone else and being taken care of. It's also been a process of working on myself, my mental health all this stuff with my therapist and unpacking all of that trauma, my realizing that when you lose somebody that's so important to you — like a mother — so early," which he did at age 10, "that creates a wound that blocks a lot of that emotional accessibility ... and vulnerability."
He continued, "It's only been in the last couple of years of me kind of sitting down and really thinking about all that stuff 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."