Making "Jeopardy!"
Once I knew what the basic idea was — Benjamin and Jeremy playing Jeopardy! against Watson — a whole bunch of questions emerged. The biggest one was that if we tried to use the earnings to represent the new year ($1, $1, $2018), either Watson would be creaming our kids or one of Benjamin or Jeremy would be doing much better than the other. Eventually I dismissed this concern and decided I would just place the contestants into the picture in the way that looked best.
Another question was how we'd spell out Happy New Year. Jeopardy! has each contestant write their name in their own handwriting, so eventually I had Benjamin and Jeremy each write out the words using the mouse. After a few tries they each got something that looked reasonable. I just used a normal typewriter font for Watson.