Watchworthy
57 voters

Personal Assistants To Tyrannical Movie Bosses, Ranked By Whether They Deserve A Raise

Updated July 1, 2021 388 votes 57 voters12 items

List RulesVote up the put-upon personal assistants who've earned a hefty raise - and a vacation.

Being an assistant can be a thankless job. No matter what amazing things they do, those duties are simply a part of the job. But if there’s a mistake, there’s hell to pay. Being an assistant in a workplace comedy or drama is much worse. It goes beyond making travel plans and answering phones to being a full-time servant. This can lead to funny scenarios and hijinks, but it's definitely not a job any HR department would allow in the real world. 

Whether they’re called personal assistants, secretaries, or executive assistants, these unsung heroes keep their bosses at their best. They appear to bend reality as they make the impossible possible, and yet are still ready for more. They stay late, do degrading tasks, and still seem committed to making the best of things. Here’s a collection of some of the best, but most poorly treated, assistants in film history. They are desperately in need of a raise - or maybe just a transfer.

Photo:
Discover your next favorite show with the ultimate Streaming TV guide and watchlist.Try our free app
  • Who’s The Assistant? Aspiring journalist Andrea “Andy” Sachs (Anne Hathaway) gets the opportunity to interview for Runway magazine. While not remotely a fashionista, she takes the job because it will open up a ton of opportunity. Over time, she starts giving more of her time and attention to try and help her unpleasable boss. Eventually, Andy gets an epic makeover and finds herself doing unscrupulous things to succeed. However, the struggle between her integrity and her ambition becomes a major part of this comedy. 

    Who’s The Boss? Miranda Priestly (Meryl Streep) runs fashion behemoth Runway magazine. Imagine Vogue and Anna Wintour, but unofficially. Miranda runs her magazine with an iron fist. Women must wear heels at all times. She likes things her way or not at all. She asks for the impossible like travel plans during a hurricane or a copy of the top-secret Harry Potter manuscript during the height of the book's popularity. And, if you displease her, be prepared for a scathing verbal lashing and her purse thrown in your face. 

    Most Humiliating Moment: While Andy faces many indignities, the popular cerulean smackdown is an epic burn. Andy scoffs at two belts looking exactly the same. And she gets a verbal lashing from Miranda in front of the entire editorial team. She breaks down the entire fashion industry while also pointing out that Andy is far from being as individual as she thinks.

    44
    13
    Do they deserve a raise?
  • Who’s The Assistant? Grace Cooley (Alfre Woodard) is a hardworking mother of four who plays assistant to the head of the television network. She fills the role of Bob Cratchit in this modern retelling of A Christmas Carol. She does everything asked of her, from mixing cocktails to having someone fired and thrown out of the building on Christmas. Despite being an amazing assistant, she gets zero appreciation. 

    Who’s The Boss? Frank Cross (Bill Murray) is the youngest president in IBC network history. He has absolutely no scruples. He plans a live broadcast on Christmas, takes cabs from elderly women, and even tries to give his brother a bath towel for Christmas. He creates a super-shocking advertisement for a special that takes the life of a senior woman. He sees the demise as great press. 

    Most Humiliating Moment: While Grace must do many humiliating things as his assistant, standing there as Frank rips her son’s drawing off the wall and tosses it in her face takes the cake - especially since Frank only plans to give her a towel for Christmas.

    31
    8
    Do they deserve a raise?
  • Who’s The Assistant? Doralee Rhodes (Dolly Parton) is a kind Southern woman just trying to support herself and her husband. She’s overly friendly and willing to put up with a lot. But do not take her for a fool - she does carry a sidearm in her purse. She’s very intelligent and often underestimated because of her looks. 

    Who’s The Boss? Franklin Hart Jr. (Dabney Coleman) is an executive at - the ingeniously named - Consolidated Companies. He manages the secretarial pool like a tyrant. He doesn’t allow his employees to have personal items at their desk. He belittles his female employees and blocks them from getting promotions they deserve. He believes women are beneath him and, worst of all, he harasses women.

    Most Humiliating Moment: Doralee can handle Hart even when she has to fight him off from trying to sexually assault her. But the most humiliating moment is when she realizes all of her co-workers have been cold because they think she’s sleeping with her boss.

    24
    5
    Do they deserve a raise?
  • 4

    Claire Rawlings From 'The Boss'

    Who’s The Assistant? Claire Rawlings (Kristen Bell) is a single mother. She’s a skilled personal assistant and available 24 hours a day. She not only helps keep her boss’s various businesses running, she even helps her whiten her teeth. But she has not received a raise in over three years. 

    Who’s The Boss? Michelle Darnell (Melissa McCarthy) is the 47th-richest woman in the world. She is a motivational speaker, author, and businesswoman. Sadly, that money comes from insider trading. She’s a bit of a nightmare because she didn’t have people in her life growing up. So she’s not the best with personal relationships. 

    Most Humiliating Moment: Without ever receiving a raise, Claire loses her job when her boss is apprehended for insider trading. As if that’s not bad enough, Michelle has no one else in her life, and she asks Claire for a place to stay. Claire ends up having to not just raise her daughter but also still deal with her overbearing former boss. Working for free is fairly humiliating. 

    21
    2
    Do they deserve a raise?