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The Boss: Mr. Sheldrake (Fred MacMurray), The Apartment (1960)
The Employee: C.C. Baxter (Jack Lemmon)
The Issue: Expecting Baxter to let him use his apartment to seduce the apple of his eye, Miss Kubelik (Shirley MacLaine).
The Lesson: Tell your bosses to consult the Hilton.
The Boss: Franklin Hart, Jr. (Dabney Coleman), 9 to 5 (1980)
The Employees: Judy Bernly (Jane Fonda), Violet Newstead (Lily Tomlin) and Doralee Rhodes (Dolly Parton)
The Issue: Being a "sexist, egotistical, lying, hypocritical bigot" ought to do it.
The Lesson: Recruit your fellow girlbosses. Document everything.
The Bosses: Randolph & Mortimer Duke (Ralph Bellamy & Don Ameche), Trading Places (1983)
The Employee: Louis Winthorpe III (Dan Akroyd)
The Issue: Framing an employee for theft and ruining his life out of sheer boredom.
The Lesson: Trust no-one, and avoid working for fat cats who treat humans like Legos.
The Boss: Gordan Gekko (Michael Douglas), Wall Street (1987)
The Employee: Bud Fox (Charlie Sheen)
The Issue: Espousing "greed is good," pursuing a deal that would put Bud's father out of work, and general shadiness.
The Lesson: Don't break the law. Never betray your family.