He may be one of the most talented actors on TV today, but the '90s weren't as kind to Jon Hamm.

The Mad Men star, whose 1996 appearance on a dating show recently surfaced, admits the mid '90s were a low point in his life and competing on game shows wasn't all he was doing.

"I was actually at that time working as a set dresser for Cinemax soft-core-porn movies," he shares, calling the experience "soul-crushing."

Hamm competing on "The Big Date"

Now that he's played ad exec Don Draper for seven years on the widely popular AMC series — along with roles in a slew of successful films — the 43-year-old is just as grateful for landing the gig.

"This is the best job I've ever had and maybe ever will have in my life — it's so fun to play all of this," Jon tells Vanity Fair.

"It can be relentlessly dark. It can be terribly sexually inappropriate, is a way to say it. But who else gets a chance to do any of that stuff? There's so much there," he adds.

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Hamm in a still from "Mad Men's" final season

In the magazine's June issue, the Million Dollar Arm star also recalls a fun anecdote about fellow actor Paul Rudd, who shared a mutual friend with the Golden Globe-winner.

Though Jon had taken his friend Sarah Clarke to the prom, she seemed more interested in Paul, whom she met through her brother, Preston Clarke.

"I thought [Paul] was coming to visit me," Preston tells VF, "but obviously he was coming to visit my sister. Hamm was there because he was always at my house…[Paul] was slightly intimidated."

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Hamm with Rudd in 2009

And the This is 40 star remembers feeling inferior. "He seemed like he was a good-looking, athletic guy who possessed qualities I did not possess," Paul says. "We were playing Trivial Pursuit in teams…and I was like, 'Oh great, this guy is smart, too.'"

He remembers, "They would ask a question like, 'What is the largest lake in Africa?' and Jon immediately went, 'Lake Victoria.' I felt so emasculated in the game that, as a result, I started reading atlases."

We love these pre-Hollywood star stories! Keep them coming, guys!