Azumanga Daioh, Working!! Recommendations
Both have their main focus on different/unique/strange characters and both have a rather bizarre sense of humor.
They are both based off of 4- panel comics!!! They both have a fun a crazy feel to them. Both have a character for pretty much everything.
Besides the fact that both of these series are based off a four panel manga, they both also share a very laid back kind of humor. Both are very easy to watch title for new and old anime fans alike.
Both are focused around several short scenes per episode, all loosely connected.