1. Giuseppe Andrews as Deputy Winston in Cabin Fever (2002)
2. Jeffrey Wright as Winston in Broken Flowers (2005)
3. Tommy 'Tiny' Lister as Winston in Jackie Brown (1997)
4. Harvey Keitel as Winston 'The Wolf' Wolfe in Pulp Fiction (1994)
5 (tie). Ernie Hudson as Winston Zeddmore in Ghost Busters (1984)
5 (tie). Arsenio Hall as Winston Zeddmore in The Real Ghost Busters (1986)
Addendum: Bottom Two Dudes Named Winston from Film and Television
1. Mario Van Peebles as Winston in Hot Shot (1987)
2. Michael Perl as Winston Egbert in Sweet Valley High (1994)
Please forgive me for this one. Not only is it incredibly lame but I realized far too late that he should have bones for hands.
George W. Bush
George H. W. Bush
I started drawing this before I found the Wacky Packages version.
I used to think these were hilarious ... when I was 10.