Durarara!!x2 Ten

The most obvious title to recommend to anyone aware of either series but Durarara and Baccano are practically siblings. They both: -deal with gangs -have an ever-changing "point of view" narrative -take place in a backdrop of a bustling city -have supernatural elements in a fairly grounded setting -have a plethora of quirky personalities -directed by Takahiro Omori -originally created by Ryohgo Narita They even have characters from Baccano (Isaac and Miria) make cameo appearances in Drrr. While the quality of both is heavily debated, there's no denying the similarities they share.  

Both are the continuation of their respective series with the number 2 in their titles. The stories in both shows gets serious but at the same time receive controversy and criticism from fans alike. No to mention character development and action have more emphasis than their prequels. The conclusions in both series are a defining factor of what the show represents leading to more sequels. 

Both start of as lighthearted stories featuring a protagonist who starts off an adventure filled with mysteries. Later it would get serious and dark with formidable enemies coming in. 

This is the 3rd season for both anime. Similar atmosphere in they are more serious, more backstories, and less comical. Not to say, there aren't any funny moments either. Similar feelings in it's always funny when the team crashes over at Kagami's house and in Durarara Ten, what happens anytime someone mess with Shizuo I'm sure you know! There is also more Shizuo X Vorona love in this season!  

Both Kuroko and Mikado turns from passive to active. Kuroko used to just pass balls being a supporter player while Mikado used to unofficially run a free for all gang called the Dollars, but never as leader. In this season, Kuroko learns to shoot basketball. Mikado learns to act on his own as he takes on the role of leader of the gang Blue Squares and goes out fighting bad people in the Dollars. The path Mikado takes though makes him fall into depravity while Kuroko at most feels down when the opponent sees through his secret to playing ball.