What killed his chances of winning Hit Me was picking the Actifed late in the game. The tea was a six and the christmas ornament would have been an eight ($39.92/8=$4.99), and picking either of those would have caused him to bust. The only safe move was to pick the vitamins to find the ace, giving him 17. The house could have pushed or busted with a hit on its hand of 15.
Besides the ace and the ten/face card, the other four cards in Hit Me added up to 20 (or 21 in rare cases). One contestant on February 1, 2001, maybe she did not know what she was doing, picked the other four cards, stayed on 20, and won on a push.
Other than not having a rule on how to treat aces in the house (stay on a soft 17-20 or hit on it until a hard 17-20 is reached or the house busts), people did not know what they were doing and some people were amazed that they won Hit Me at all. I still miss the game, but maybe it's for the best that it's retired (heaven knows Drew would bumble through explaining the game).