Deadwood: Ranking 15 Cast Members Worst To Best
6. Cy Tolliver
The late legend Powers Boothe was simply fantastic as the mean and sadistic Cy Tolliver. Owner of the Bella Union Saloon and direct rival to Al Swearengen, Cy was an abhorrent and cruel man who had aspirations of slowly taking over the camp.
It is easy to look at Cy as just Al Swearengen-light but there is a lot more to Cy than that. His obsessive relationship and unrequited affections for Joanie and his incessant power plays in the camp highlight a fragile insecurity in Cy. He is a man who wants things a certain way but often it seems like the world is against him and that only feeds into his psychopathy.
Cy becomes increasingly unhinged over the course of the three seasons, culminating in him brutally murdering one of his subordinates for seemingly no reason. It is sad that Powers Boothe passed away before filming on Deadwood: The Movie could begin as we'll never know quite what David Milch envisioned for his character. Regardless, what we got were three great seasons of a dangerous man slowly losing his mind.