For self-set parameters to this broad request, I'm concentrating (mostly)
on films set in offices or factories.  No gangsters, military films, etc.
 
The boss who orders the massacre of strikers (inspired by the Homestead Strike)
in INTOLERANCE
 
Evil capitalists in Eisenstein's STRIKE and Pudovkin's THE MOTHER.
 
The master of Fritz Lang's METROPOLIS (even though he has a change of heart)
 
The Taylorite factory bosses of MODERN TIMES
 
The evil boss in Renoir's THE CRIME OF M. LANGE
 
The sex-harassing boss of Mizoguchi's OSAKA ELEGY
 
"Stinky," the drugstore manager in THE BEST YEARS OF OUR LIVES
 
Edward Arnold as the fascist publisher in MEET JOHN DOE
 
The sex-harassing ringmaster at Betty Boop's circus in "Boop-Boop-a-Doop"
 
Salami, the factory owner in Godard's TOUT VA BIEN
 
Fred Gwynne as the deliciously lugubrious English Dept. Chairman in SO FINE
 
The title character of INSECT WOMAN and her former boss in the brothel, as well
 
Evil studio bosses harassing writer Jack Palance in THE BIG KNIFE
 
The evil uncle/husband/boss of JU DOU
 
 
Some others:
Was Mr. Dithers featured in the BLONDIE films, with Penny Singleton and Arthur
 Lake?
 
A spate of films about board room power struggles in the 1950s, including
        THE MAN IN THE GRAY FLANNEL SUIT, EXECUTIVE SUITE, IT'S A WOMAN'S WORLD [sic!]
 
Rudy Vallee in HOW TO SUCCEED IN BUSINESS WITHOUT REALLY TRYING
 
Ginger Rogers as an overworked and undersexed businesswoman in LADY IN THE DARK
 
 
 
More recent films:
TAKE THIS JOB AND SHOVE IT (self-explanatory?)
Michael Douglas in WALL STREET
Sigourney Weaver in WORKING GIRL
The factory bosses and union bosses in Paul Schrader's BLUE COLLAR
Dabney Coleman in NINE TO FIVE (bad film, good example)
 
Paul Newman in THE HUDSUCKER PROXY (and Tim Robbins until he reforms)
Tommy Smothers becomes a mean boss (and reforms) in Brian De Palma's little-seen
        GET TO KNOW YOUR RABBIT
 
The Ultimate Iconic Mean Boss Who Reforms--Ebeneezer Scrooge in any of the film
        versions of A CHRISTMAS CAROL
 
Julia Roberts winds up working for Dr. Jekyll (bad idea!) in the forthcoming
        MARY REILLY
 
And the Ultimate TV Bad Boss--Miles Drentell (sp?) in THIRTY-SOMETHING
 
 
Don Larsson, Mankato State U (MN)
 
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