The idea behind using a combination of arrogance and humor is to stand out from the crowd. With the right kind of line, it is possible to show humor, confidence, approachability and an understanding of social values. Nobody is really attracted to arrogant people, in the same way they are not really attracted to clowns. However, if the two attributes are combined with finesse, they are a magical combination.
Arrogant humor is a combination of being funny and self-assured at the same time. This is a great combination of attributes that, for a first impression, can go a long way. However, major blunders with arrogant humor are to go too far or to fluff the line that seemed witty before being spoken. The perpetrator then comes across as a little nasty or just downright insulting. No good comes from making someone think they are being insulted.
Although arrogant humor is a natural way for some to express themselves, it is often a tactic employed to impress. As such, it may only work on occasion and has the potential for absolute disaster when it comes to impressing others. It all depends on a person's natural character and the environment they are in. At times, other ways of addressing people may be more suitable.