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(#1) Andrea Sachs
- The Devil Wears Prada
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.
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(#2) Grace Cooley
- Scrooged
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.
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(#3) Doralee Rhodes
- 9 to 5
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.
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(#4) Andrew Paxton
- The Proposal
Who’s The Assistant? Andrew Paxton (Ryan Reynolds) is an aspiring editor. He hopes that by dealing with his overbearing boss, he will get to help shape publishing.
Who’s The Boss? Margaret Tate (Sandra Bullock) is the executive editor-in-chief of New York publishing company Colden Books. She is cold and asks for a lot. She requires late nights and weekends, yet is still gruff and dismissive with Andrew.
Most Humiliating Moment: While it’s embarrassing, Andrew drinks the same coffee order as Margaret in case he spills. Also, being forced to marry his boss is pretty humiliating. Margaret strong-arms Andrew into committing a transgression to keep his job. Worse than that, in true rom-com fashion, she confesses their plot to Andrew's entire family on their wedding day. That’s a lot to bounce back from.
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(#5) Tess McGill
- Working Girl, Working Girl
Who’s The Assistant? Tess McGill (Melanie Griffith) is an enterprising woman from Staten Island. Despite her working-class upbringing, she has her eyes set on a career in Manhattan’s finance industry. She’s worked as a secretary for multiple men who have disrespected her based on her looks. One even sends her to a meeting with a man who uses illicit substances and tries to sexually assault her. As an assistant, she’s not only willing to do anything and everything, she also has strong ambition, which she describes as "a head for business and a body for sin."
Who’s The Boss? Katharine Parker (Sigourney Weaver) is the opposite of Tess. She’s worldly and cosmopolitan. At first, she appears to be about creating a respectful and equal working environment. She even lets Tess share ideas. But soon, Tess finds herself helping her boss try on ski boots and housesitting for her. She also learns Katharine took her idea and passed it off as her own.
Most Humiliating Moment: While it is unfortunate to have an idea taken without being credited, Katharine having Tess destarch her dress and underwear while she’s wearing them is pretty degrading.
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(#6) Zara Young From 'Jurassic World'
Who’s The Assistant? Zara Young (Katie McGrath) is on it. She’s composed and constantly has her eye on the prize. She’s even completely willing to babysit two teenage boys.
Who’s The Boss? Claire Dearing (Bryce Dallas Howard) is the park operations manager of Jurassic World. She takes type-A to a new extreme. After all, she spends most of a life-threatening situation running in heels. She’s all business and, while she’s not the worst boss on this list, she definitely does have her priorities out of order. Also, considering the number of lives lost, she may not be the best at her job.
Most Humiliating Moment: Zara’s last moments on Earth are horrifying. She’s pulled into the air by a Pteranodon, only to be dropped and fought over by another Pteranodon, then eaten by the epic Mosasaurus.
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(#7) Catwoman
- Maggie, Catwoman, Batman: New Times, Grayson, Batman: The Dark Knight Returns, Part 2, Fight Batman Fight!, Batman: Year One, DC Showcase: Catwoman, Batman, The Dark Knight Rises, Batman Returns, Alyas Batman en Robin, DC Universe
Who’s The Assistant? Selina Kyle (Michelle Pfeiffer) is painfully single and insanely shy. Focused on doing the best job possible, she’s awkward and so anxious she often stumbles over her words. She is making her best effort but is still completely dismissed by her boss.
Who’s The Boss? Max Schreck (Christopher Walken) is a real-estate developer, owner of the local department store, and overall horrible capitalist. It is an understatement to say he's dishonest. He’s slain people. He dismisses Selina and treats her like a coffee wench. When she stumbles onto one of his secret plots, he attempts to off her.
Most Humiliating Moment: This one is a tie. Selina tries to interject at a meeting, but Max is quick to dismiss her in front of Bruce Wayne (Michael Keaton) in a totally degrading way. Bring thrown out of a window of a huge office building does come in a close second. Although, that does turn her into Catwoman.
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(#8) Lee Holloway
- Secretary
Who’s The Assistant? Lee Holloway (Maggie Gyllenhaal) is socially awkward and struggling with some emotional issues from her dysfunctional past. She self-harms and has signed up for a position as a secretary despite being overqualified. On some level, she’s submissive and enjoys being subservient to her boss.
Who’s The Boss? E. Edward Grey (James Spader) is an eccentric attorney and a total control freak. He's like Grey way before Fifty Shades of Grey. He has kinky, sadistic predilections that he takes out on his assistant.
Most Humiliating Moment: While Grey and Lee do engage in some kinky office activities, the most humiliating part comes at the end of the film. Lee comes back to Grey to enter into a relationship with him. He asks her to sit there and not move. She sits there for three days and even makes a mess of herself.
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(#9) 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.
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(#10) Guy From 'Swimming with Sharks'
Who’s The Assistant? Guy (Frank Whaley) is a recent film grad with his eye on a career in the film industry. He’s ambitious and optimistic, and believes that he has what it takes to make it in the entertainment industry. He's professional and really does try to be the nicest he can be in the office.
Who’s The Boss? Buddy Ackerman (Kevin Spacey) is a movie mogul and total nightmare of a human being. He’s not above publicly belittling his assistants and talking to them like they are garbage. He makes impossible requests like trashing every issue of Time magazine or staying at the office after 11 pm to record a program. He takes out his workplace anxiety and personal issues on his assistant, perpetuating the cycle of overworked assistants in the movie industry.
Most Humiliating Moment: Guys asks Buddy to speak to him with respect and not yell at him in front of his co-workers. Buddy proceeds to tell him he is “nothing” and needs to “be a man.” Buddy pelts him with office supplies and tells him he "doesn’t matter." This is one of the key moments that causes Guy to eventually turn on Buddy.
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(#11) Studio Executive Rob Slolom
- Tropic Thunder
Who’s The Assistant? Studio executive Rob Slolom (Bill Hader) is the ultimate yes man. While an executive in his own right, he’s way more focused on pleasing his boss than on making a good movie. He’s also hilariously unaware of what goes into filmmaking and will often just state the obvious.
Who’s The Boss? Les Grossman (Tom Cruise) is the typical foul-mouthed, money-obsessed Hollywood stereotype. He’s focused more on money than the safety of his stars. He also finds ways to hilariously insert disgusting phrases and filthy terminology into normal conversation. Plus, he's not above telling his assistant, “A nutless monkey could do your job.”
Most Humiliating Moment: While Rob doesn't get humiliated, it has more to do with his lack of shame. When Rob agrees with Les to the point of saying, “You spank that [butt], Les!” it does not do wonders for his credibility or dignity.
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(#12) Lucy Kelson
- Two Weeks Notice
Who’s The Assistant? Lucy Kelson (Sandra Bullock) is a wildly intelligent but somewhat frumpy lawyer. She has insane professional qualifications and becomes lead counsel for a real-estate developer. But he treats her as his de facto assistant. He calls her at all hours, and she complies by going above and beyond her paygrade.
Who’s The Boss? George Wade (Hugh Grant) is an arrogant billionaire real-estate developer. He has little integrity and even less self-control. He’s not above calling Lucy at all hours despite her being a lawyer and not his assistant. He also does not keep his word to Lucy despite her unwavering loyalty. Plus, his philandering ways are grossly unprofessional.
Most Humiliating Moment: George texts Lucy that he is having an emergency. She leaves as a bridesmaid at her friend’s wedding only to find he wanted help choosing an outfit.
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About This Tool
Behind every successful boss or executive is a personal assistant who works around the clock to make their boss look great, and all work arrangements are in order, even on TV and movies. Assistants play an important role in many movies and have shaped many people’s illusions about the work of personal assistants. Some of our favorite fictional personal assistants often face the same harsh bosses on the screen as in real life.
It seems that excellent personal assistants can often save everything in trouble, but the work of the personal assistant is not as gorgeous and interesting as in the movie. The random tool lists 12 famous personal assistant roles in movies.
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