These 16 words can be separated into 4 categories... What are they? All of them have something in common... What is it?
Bean, Iron, Bird, Notorious, Cannonball, Ripper, Prince, Zodiac, Clown, Slim, Sam, Dr, Dizzy, Fifty, Sugar, Brown
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The overall connection is
As a starting point, one potential group seems to be
Serial killers: Zodiac (Killer), (Son of) Sam, (Jack the) Ripper, (Killer) Clown (John Wayne Gacy)
Another group is formed by:
Rappers: Fifty (Cent), Slim (Shady), Notorious (B.I.G), Dr (Dre)
(Charlie) Bird (Parker), Dizzy (Gillespie) and presumably two other jazz musicians. Bean (Coleman Hawkins) and Cannonball (Julian Adderley) must be the other two as they're the remaining words.
The fourth category might be
Boxers: Sugar (Ray Leonard), Iron (Mike Tyson), Prince (Naseem Hamid), Brown (Bomber) (Joe Louis)
Note on solving:
Zodiac, Ripper and Sam jumped out as serial killer names; Notorious pointed towards rappers and Slim and Fifty obviously went there; Dizzy and then Bird gave the jazz group; and Sugar pointed towards the boxers. Though I did have Dr in the serial killers initially, and Prince in with singers. And pretty much any word looks like it could a jazz nickname based on the list on Wikipedia.