Not only was he a struggling actor, but the 43 year-old didn't find any success when appearing on 'The Big Date' in 1996 as he was passed by two women.
Age was been kind to Jon Hamm.
Before finding success in the television and film industry, a 25 year-old wannabe actor appeared on a dating show called 'The Big Date' in 1996.
Luckily for Hamm's fans, but not so much for him, footage of the episode was uploaded to YouTube on Friday (April 4th), and it is a very amusing watch.
The 'Mad Men' actor, who was waiting tables at the time, was trying to attract the attention of a 25 year-old computer animations student, Mary.
She desired to pick "a sexy, hot man who is honest and knows how to give a good foot massage."
But it seems Hamm just didn't match Mary's criteria.
While sporting a 'very 90's' long and wavy haircut, the now 43 year-old was asked by the show's host, Mark L. Walberg, how he would make someone of the opposite sex feel special on their first date.
"I'd start out with some fabulous food, fabulous conversation, a fabulous foot massage for an evening of total fabulosity," Hamm replied.
But unfortunately the two other men he was competing against had more to offer Mary, who went on to pick a stuntman called Mark.
Watch Jon Hamm's appearance on 'The Big Date' below
The second female guest on the show, Sonia, also chose not to go with the struggling actor and settled on a finance major called Marcus.
Although it may have been an embarrassing moment for Hamm, it didn't last too long as he has gone on to become one of Hollywood's most desired hunk's and has forged a very successful show business career.
Undoubtedly Mary and Sonia will be regretting their decision on that day.
Hamm is currently in a 17 year-long relationship with the gorgeous 'Kissing Jessica Stein' actress Jennifer Westfeldt.
If any Hamm fans need to forget watching his appearance on 'The Big Date', the final season of 'Mad Men' premieres on April 13th at 10 pm on AMC.