The "Crooked Smile" aspect of the song refers to J. Cole's character being the weed dealer and the stigma that goes along with those who sell weed/drugs. But in this case (in my opinion) he is using the money he makes to put his daughter through the same school the DEA agent's daughter went to. The similarities between the two characters (J. Cole's and the DEA) is apparent in that they both are doing what they feel is right in order to support their daughters; one just happens to be illegal.
This is a great vid.
I drive a Stratus home boy!