Jon Hamm as Young Pilot #2 in Space Cowboys (2001)
A role with a number next to it is not exactly a promising start. For Jon Hamm, it was Young Pilot # 2 in the Clint Eastwood movie, Space Cowboys. He would continue to gain independent film work and a slew of one-off episdoes in mainstream network television fare like CSI:Miami. Eventually, he landed a landmark role of Don Something in this show called Mad Men about sad dudes in suits or something. It might still be on. All in all, he's apparently doing much better now.