Factual error: When it's 1969 we see a boy (I'm not sure which one so you'll have to look) riding a Shwinn Sting-Ray Krate Grey. That bike didn't come out until 1971 and they only made them that one year. (00:02:45)
Factual error: Carl tells Alan that his police cruiser is brand new, but the Chevrolet Caprice he is driving is a 1991 or 1992 model as it has "skirted" rear wheel wells.
Chosen answer: Most games don't need you to roll the exact number of spaces left in order for someone to win. By rolling twelve he gets to move his ten spaces & has won. I'm assuming it's easier for him to roll two sixes than anything else.