Hamm's appearance on The Big Date back in 1996 saw him appear with unfashionably floppy hair parted in the middle. Perhaps, more humiliatingly - he ended up not being picked.
Fortunately, Hamm has enjoyed a career resurgence since the advent of the AMC advertising drama set in the 1960s.
Unsurprisingly, he doesn't think he'll ever get a better job than playing the anti-hero in the show, which will end next after its current seventh season.
Speaking to the magazine, he said: "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.
"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."
Hamm is also heavily involved with the plotlines of the drama, with show creator Matthew Weiner admitting he knows "everything" that is going to happen and the writers often go to the actor for suggestions when they get "stuck".
Weiner said: "He knows everything. He's the first, outside the writers' room. I try stuff out on him. When we get stuck in the writers' room, I go down there and have a conversation with him."
The last season of Mad Men has been split into two parts with the second half to air in 2015.
- Daily Mail
