Got it! They all played mayors of New York -- two real, three fictional.
Gandolfini -- The Taking of Pelham 123 (remake)
Woods -- Rudy: The Rudy Giuliani Story
Pacino -- City Hall
Hurt -- Noise
Hope -- Beau James (Jimmy Walker)
And Bob Hope was the right place to start.

New one. In what movie is Brendan Gleeson's character killed by a pack of trained "warrior" dogs?