Almost to number one in my count down as we come to number two, Kisuke Urahara. Urahara is one of the most important figures in the entire series and is often the one that is at the root of everything that happens in the series. His story is a very unique one and brings a lot of laughter along the way.
Urahara used to be a lieutenant under squad 2 before he was promoted to squad 12 captain and created the research and development group, transforming the squad into the science authority of soul society. After that, he was forced to leave due to the actions of Aizen where he entered the real world and became a humble shop owner. However, despite his store, he is still connected to the soul society, he is still pulling the strings on nearly everything and has a hand in it all.
Urahara has a hand in everything it seems during the entire story. He is a former captain and a skilled warrior, but prefers to use his technique and knowledge rather than drawing his sword. He tries to play dumb the entire time, often rewarding people for guessing the right answers to the easiest situations. However, if he is pushed he is deadly with both his blade and his advanced kido skills that can stop anyone.
His zanpakuto is one of my favorites, Benihime. It is a “female” blade and uses kido to attack and has attack terms like “scream” and “play with fire” as its attack commands. He does have a bankai but has never shown it while stating it is not a type that can help people. With that said, along with this knowledge and kido, Urahara is a feared fighter even if he chooses to sit and watch most of the time. Opponents are fools to go after him.
So what about the humor factor? Urahara is one of the funniest characters in the entire series. Recall how I said he often patronizes people for their knowledge, that often leads to him getting hit in the face. His relationship with Hiyori was another mark of his humor. He is a very deep character that may at first seem goofy and strange, but is calculated and deadly. He often will talk as if everything is OK then will finalize his report with the ugly truth.