10 Best and Worst Movie Bosses

6:30 PM 9/27/2015

by THR staff

From 'The Devil Wears Prada' to 'Working Girl,' these ten films feature the employers you love, hate and love to hate.

Devil Wears Prada - H 2015

Devil Wears Prada - H 2015

  • Worst: Working Girl

    Sigourney Weaver stars as a financial executive who encourages her secretary (played by Melanie Griffith) to share business pitches only to later devise a scheme to steal her ideas and claim them as her own.

  • Worst: The Proposal

    In the 2009 film, Sandra Bullock plays an overbearing boss who forces her assistant (Ryan Reynolds) to marry her when she learns that she may face deportation to Canada due to an expired visa.

  • Best: Big

    When 12-year-old Josh Baskin's (Tom Hanks) wish to be "big" is granted and he transforms into a 30-year-old man, Mr. MacMillan, owner of MacMillan Toy Company, gives him his dream job as a toy tester. 

  • Worst: Wall Street

    Michael Douglas stars as a ruthless Wall Street player who lives by the saying that "greed is good."

  • Worst: The Devil Wears Prada

    The 2006 dramedy stars Meryl Streep in the role of Runway fashion magazine's editor-in-chief whose icy demeanor has all of the publication's employees on their guards and at her service.

  • Worst: Horrible Bosses

    Jennifer Aniston plays an aggressive dentist who has a habit of sexually harassing her assistant Dale Arbus (played by Charlie Day).

  • Best: All the President's Men

    The 1976 film stars Jason Robards as The Washington Post executive editor Ben Bradlee, who encourages staff writers Bob Woodward (Robert Redford) and Carl Bernstein (Dustin Hoffman) to dig deeper in discovering the truth behind the infamous Watergate scandal.

  • Worst: Office Space

    Gary Cole stars as software company Initech's division vice president Bill Lumbergh, a quintessential micromanager who bogs his employees down with unnecessary paperwork and pointless demands, in the 1999 film.

  • Worst: 9 to 5

    Dabney Coleman embraces the role of a sleazy manager who mistreats his female subordinates (played by Jane Fonda, Lily Tomlin and Dolly Parton) with sexual harassment and upholds sexist hiring practices in his office.

  • Best: The Intern

    Anne Hathaway plays a young CEO of an online fashion company who develops an unusual friendship with one of the company's interns, a 70-year-old man (Robert De Niro) who joins the firm as part of a community outreach program, in the newly released comedy by Nancy Meyers.