I resisted the urge to make a Hope related title pun. Seems like these days you can't have a single headline without a pun no matter how laborious. This Christopher Hitchens' article via Slate about Bob Hope is a pretty solid (albiet acerbic) analysis of the old man. I saw quite a few of his specials growing up, and waded through a movie or two... I can attest he's not directly funny. However, I still enjoyed his work. For lack of a better analogy, if you took the derivative of his act it might be funny. His timing, style, and joke construction was totally predictable, and that was his secret. Once familar with his patterns, laughter was a Pavlovian response... even though the punchline often failed to reward.