Jon Hamm
Jon Hamm is known for being one of the most dapper men in America, thanks to his role as the brooding, suave Don Draper on Mad Men. But did you know one of Hollywood's top leading men was on a reality dating show? Yes, the guy who shamed Kim Kardashian for her reality TV success was at one point on The Big Date. Because apparently even one of the best looking dudes ever had trouble finding love. Once you watch the clip, you'll see that Jon hasn't even hit his peak yet, largely due to his awful haircut and awkward game. But for those of you out there who are working a job you hate right now, even Jon Hamm himself had to suffer a few terrible jobs before joining the creme de la creme of Hollywood.
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