Regarding the dubious reputation of the $2 bill, I can cite some evidence supporting a couple of the claims in the video. One is with gambling. When I was a coin collecting kid and saw a $2 bill for the first time (maybe 1965), I asked my parents why nobody uses them. My mother, who had a more interesting and diverse background than many women of her day, told me that $2 was the minimum bet at the horse races, and you would only see them there. If you had a $2 bill, people would assume you were a gambler, which at that time before state lotteries and Indian casinos was considered a vice.

The second claim can be confirmed from a World War II Sad Sack cartoon I have a copy of, from when it was intended for US Army personnel (about 1943, no words, just a series of a few drawings for each strip to illustrate the soldiers' common gripes). Everything is covered, from army food to unkind sergeants.

In one, Sad Sack gets paid, and goes out on a drinking binge. Next panel, he has two pieces of paper money left and that he is eyeing in his hand. Next, he is talking to a beautiful girl. Then she is leading him somewhere, as he eyes her rear end. In the final panel, she is leading him to a church bazaar, admission $1 per person, and he is frowning and digging in his heels. This seems to imply that a lady of the evening would commonly be $2 at the time. Therefore, I think I could easily believe the gambling and prostitution associations.