James was a memorable contestant, because Drew prompted him about his train hobby and James offered that interesting statement about his wife letting him keep his trains in the living room if she can store her dolls underneath. Those are the kinds of things that make the contestants interesting, and the kinds of things I hope Drew can draw out of contestants more in the future.
In fact, that whole segment was going well until Drew started talking about how long Ten Chances takes. The reason that Drew finds Ten Chances to be long and frustrating is because he makes it long and frustrating. This playing is another example of why. After James chose reasonable but incorrect prices the first four times for the guitar, instead of offering any words of encouragement, Drew's spirit dropped right along with James when James said that he was stuck. Especially with a likable guy like James who has a clear chance of winning because he's ending all of his guesses with 0, that's when the host needs to say, "Don't get discouraged. Take a look at what you've written. We know those are wrong, but you're narrowing it down. You can get that guitar. Go to it!" Instead, Drew has already given up by pointing out that oh well, it's a nice cereal dispenser that James won.