9. Roland Daggett
It's easy to forget that, aside from having a colourful rogues gallery, Batman also tangles with mob bosses such as Carmine Falcone and Rupert Thorne.
Batman: The Animated Series introduced a new crime boss in the mould of Christopher Walken's Max Shreck from Batman Returns to challenge both Batman and Bruce Wayne: Roland Daggett.
Voiced by Edward Asner, who memorably went on to portray Granny Goodness in Superman: The Animated Series, Daggett is a corporate hack who is desperate to legitimise his own business, Daggett Industries by acquiring Wayne Enterprises. This is key to his first appearance in Feat of Clay, a two-part episode in which he unwittingly creates Matt Hagen's Clayface. He later endangered Bruce Wayne's personal friend (and Batman's private doctor), Dr. Leslie Thompkins, in Appointment in Crime Alley, and earned the ire of Catwoman in the less successful Cat Scratch Fever.
After this, it seemed that Daggett had finally been brought to justice, but he returned one last time in Batgirl Returns. Desperately in need of money, Daggett stole a priceless cat statue from Gotham University and tried to kill the unlikely pairing of Batgirl and Catwoman when they pursued him. With Robin's help, they defeated Daggett and he was presumably jailed, never to return again.
A slightly altered version of the character, named John Daggett and portrayed by Ben Mendelsohn, appeared in Christopher Nolan's 2012 film, The Dark Knight Rises.