15 Hollywood Celeb Personal Assistants Tell All

For those people who are blinded by the glitz and glamour of those in the spotlight, it’s easy to forget that Hollywood can be an unforgiving place — especially to those in the background who are burdened with the task of keeping that particular spotlight as soft as possible. Sure, being a personal assistant sounds extremely attractive. You are technically the person who's constantly a mere heartbeat away from a superstar. A personal assistant is so involved in a celebrity's day-to-day lives that they might be even closer to the celeb than some of their own family members. But when you pull back the curtain, you find that being that close to the sun has its consequences. Years ago, I myself worked for a Hollywood producer as an executive assistant, and while it was enjoyable for me to tell my friends about this exciting life I was living, it was an actual nightmare. This producer once told me that if I didn’t go home crying every single day, he wasn’t doing his job properly. But that was actually nothing compared to what these 15 assistants had to go through for a simple paycheck. I'll let you decide if it was worth it.

15 Kim Kardashian

The Inquisitr

Anyone who watches Keeping Up With the Kardashians is familiar with Kim Kardashian’s personal assistant and apparent BFF, Stephanie Sheppard. Kim is even a pro at trolling her bestie assistant: she managed to post a series of hilarious tweets wishing Sheppard a happy birthday once by only posting gorgeous pics of herself with Sheppard somewhere off in the distance in each photo. It was actually pretty funny (she did wish her assistant a heartfelt happy birthday in a tweet following the string). But does Sheppard keep mum about her boss’ odd practices? I’m pretty sure she does, so she wasn’t the assistant who leaked that Kardashian happens to save the fat she has removed from her body during her typical liposuction procedures she has done yearly. According to a source, she freezes the fat and uses it as a filler for wrinkles on her face. And wait, it’s not only saved for her face, but for her rear end as well. You have to be crazy to think that all that junk-in-the-trunk is actually nature-made.

14 Lady Gaga

New York Daily News

You have your cutesy whootesy assistant stories like Kim Kardashian’s, and then you have your “WTF, OH HOLY CRAP, WHAT IN THE WORLD??!” stories, like Lady Gaga’s former assistant’s. Once upon a time, Jennifer O’Neill thought she had the job of the century when she landed the job as the personal assistant of superstar Lady Gaga. O’Neill worked for Gaga during her Monster Ball tours and sued the singer for a crap load of back pay. O’Neill apparently “had no privacy, no chance to talk to any of [her] family, no chance to talk to any friends, no chance to have sex if I wanted to have sex,”, O’Neill apparently told the court during her deposition against Gaga. “There was no chance to do anything.” The assistant was forced to sleep in Gaga’s bed and even take a shower with her because she couldn’t do anything alone. Not only did Gaga end up settling out of court, but O’Neill is also in the process of writing a “tell-all” book about her experiences which means SHOWER STORIES FOR EVERYONE!

13 Angelina Jolie

The Inquisitr

It absolutely CANNOT be a field day being a personal assistant for the estranged former Mrs. Pitt. And it’s not just because she has an entire slew of kids, some below kindergarten age (who are hopefully potty trained?). Good news is those kids are the nanny’s issue. Bad news is that you still have to work for Angelina Jolie. A former assistant of the actress (who goes by the name Ana Charlotiaux) claims that Jolie not only suffers from alcoholism, but she locks her six kids in their bedrooms when she gets entirely too drunk. Rumors circulated that Jolie actually would make her assistants watch her movies, even the horribly crappy ones. Ms. Charlotiaux is actually in the process of suing the management of Jolie and Pittfor for 35 million dollars after she was fired from missing work due to an illness. She worked for the duo when they were married and living in France.

12 Jennifer Aniston


She once was considered “America’s Sweetheart” during her Friends days. Jennifer Aniston then moved on to become Mrs. Brad Pitt (before Jolie seemingly stole him out from under the NBC golden girl when they worked on the thriller Mr. and Mrs. Smith). However, not everyone is a fan of the Smart Water spokeswoman, including some of her former assistants. It has been said that Aniston isn’t a fan of sweat and downright refuses to be all dewy on hot days. During takes on the set of her movies, she would make her assistants either personally fan her or hold ice cubes to her face to keep her body temperature cool. This actually doesn’t seem as bad as other assistant nightmares, so I think whoever was complaining about this needs to work their way around Hollywood a little bit more before attempting to throw an actress under the bus. No one looks good with sweat stains on their clothes, come on!

11 Christian Bale


The former Batman appears to be as dark as his movie persona displays. Former assistant, Harrison Cheung revealed some odd things Christian Bale made him do while he was working for him years before. “If Christian was away filming on location, I would take care of his five pets, along with stray possums in the backyard,” Cheung said in a 2012 biography he wrote about the actor. “I would do anything from sniffing Christian’s armpits for B.O. right before he hit the red carpet to making emergency sock-runs if Christian was all out of clean ones.” Not all of that sounds too appalling (except maybe taking care of possums – who the hell does that?), so it’s hard to imagine that Cheung filled an entire book with Bale complaints. He apparently talks about Bale’s dark childhood and how it had a profound affect on his life and even how he picks his movie roles.

10 Anna Wintour


If you’re familiar with the movie The Devil Wears Prada, the little story about how Anne Hathaway’s character is brutally terrorized by Meryl Streep’s character at some fashion magazine, you’re familiar with Anna Wintour. The author of the original novel the movie was based after, Lauren Weisberger, was Mrs. Wintour’s assistant at Vogue, which means, yes, while the book is a work of fiction, a lot of the events in the story are based off of true happenings. While all of the assistants of the artistic director went on to lead glamorous careers elsewhere (hey, like Anne Hathaway’s character!), they had to go through hell in order to get there. Her nickname is even Nuclear Wintour. There was a huge controversy when the book, and later the movie, was released because it painted Wintour with the same likeness as a tyrant, which only some of her assistants have denied.

9 Jessica Simpson

Evil Beet Gossip

If you’re a fan of Jessica Simpson, you know all about her relationship with her BFF personal assistant, Cacee Cobb, who hopped on the B-List star train after working for the blonde songstress. She appeared with Jessica and then-husband Nick Lachey on their reality show Newlyweds: Nick & Jessica, and then when Jessica went solo with Jessica Simpson: A Public Affair, but then went her own way after marrying Scrubs actor Donald Faison. But before then, Simpson was said to have gone through a string of personal assistants who couldn’t stand working for her (one even quit after a couple of weeks, claiming that she was “too smart” to work for the singer). One even gossiped (via the Star) that Simpson enjoyed skipping the tab whenever she went out to restaurant or bars. Apparently, this source claimed that Simpson believed her stardom was payment enough for these establishments. Yikes!

8 Mariah Carey

Entertainment Daily

We’ve all heard the Mariah Carey-diva stories – from the crazy things she requests be in her dressing room every day when she shows up for a gig (one of the less crazy items is an array of exotic fruits) to demanding her dog have its own chauffeur. Carey certainly stands out as one of the most high-maintenance singers in history – a role I’m sure she loves endlessly. The level of stress must be extreme for personal assistants to attempt to maintain all her demands themselves. One assistant, Molly, who was seen on E! Entertainment’s reality show, Mariah’s World, even broke down crying because she couldn’t get the star’s Apple TV working correctly at her hotel in the UK. “The Apple TV is the most important thing for Ms. MC,” Molly said direly. “If she can’t have the Apple TV playing while she’s sleeping, then she can’t sleep. If she can’t sleep, she can’t perform.” It took Carey’s entire staff to console Molly when she (and hotel employees) couldn’t get the device to work. Thing is, Molly isn’t allowed to cry while working (nor is she allowed to date anyone for a year), so she probably was in more trouble after that mini meltdown than for the Apple TV failing to work.

7 Kylie Jenner


Chances are when a superstar allows their personal assistant to “open up” about the work they do, it’s not going to be very revealing. This is what, I’m sure, Victoria Gamero went through when she talked about having to work for the youngest Jenner/Kardashian on Kylie Jenner’s app. At first, Victoria started out as Kylie’s house manager who was in charge of making sure her household ran as smoothly as possible by having her place always stocked with groceries and doing maintenance on her cars. She then moved up to being a personal assistant, which meant she was on call 24/7, which has to be extremely stressful, despite how easy Gamero makes it sound. A couple of her other assistants joked about Kylie’s particular smoothie obsession via Snapchat. They joked that Kylie demands her assistants should know exactly what type of smooth she wants and that she won’t drink it if the straw has been touched or if it’s too warm.

6 Naomi Campbell


Supermodel Naomi Campbell has been long known to be a terror to people who are employed by her. Not so long ago, former assistant, Amie Castaldo made claims that she had to flee her job as Campbell’s personal assistant due to a “month-long reign of abuse” that was inflected upon her. Cataldo claimed that the model physically attacked her, head butted her, bit her on the lip, called her a “f***ing worthless b*tch”, and even pulled her hair in one traumatic experience. Castaldo filed a suit against her former boss and reported that “Naomi hundred percent needs to get help. She was incredibly mean to me and very cruel. She would scream at me every day – in public places – in front of people I knew. It really didn’t matter.” Castaldo claimed to be the model’s personal punching bag. This almost puts every other personal assistant story to shame.

5 Taryn Manning


While Taryn Manning character on Netflix’s hit series, Orange is the New Black, is a violent offender, it appears her real life persona can be just as violent and cruel. A few years ago, Manning had to appear in court after her former assistant filed a lawsuit against her for choking and punching the woman. The court ordered the actress to stay away from her former assistant after photos were released that showed the bruising on the body of the young woman after Manning allegedly attacked her and even slammed her head into a wall. Manning’s lawyer claimed that the assistant was actually a “long-time friend" of Manning’s entire family and even stays with Manning’s mother from time to time. Even if she was a longtime friend as the lawyer claimed, that gives her no right to physically abuse someone she claims to be a friend. While it can be considered unforgivable to most people, the assistant apparently “forgave” the actress later down the line.

4 Justin Bieber


We’ve heard a lot of wild stories over the years about the antics of the young Canadian pop star who rose to fame. A few years ago, Bieber was touring Australia and happened to be busted for carrying an illegal substance at the airport. Genius move on his part. However, while the singer was just slapped on the wrist with a 12-month good behavior bond, his personal assistant, Terrence Reche Smalls, appears to have taken a majority of the heat. Smalls pleaded guilty to two charges of importing marijuana (13 grams) and was handed a 12-month good behavior bond, as well as having to pay a fine of $1,000. That’s not the only thing: apparently, Bieber has to stick with male personal assistants because he tends to enjoy embarking in intimate flirtatious relationships with his more attractive female staffers. Try to keep it in your pants, bro.

3 Sarah Jessica Parker

Marie Claire

The former Sex in the City star has been known to take good care of her personal assistants. She pays extremely well (six figures a year) and was even the bridesmaid of her former assistant, Melinda Relyea, during her seaside wedding. Parker’s requirements for hiring an assistant is rather high, which could explain why her relationships with her personal assistants always work out so well. One requirement is education (the higher the degree, the better). And if the degree is from an Ivy League university – jackpot. Although, I’ve never met someone who desires to go to Harvard University in order to become the go-to ice coffee delivery person for a celebrity. While she apparently is a super boss, some oddities that Parker does in her everyday life have been revealed by former assistants. One of which being she practices witchcraft. While it’s not known how much witchcraft she practices, this does make sense considering she took that one role in the movie Hocus Pocus.

2 Madonna


This former 1980’s pop superstar appears to ALWAYS be at the height of her game. Whether she’s starring in a movie (that probably totally tank – her bizarre fake British accent is always a weird turn-off), or going back on tour, Madonna is always on the go. It’s known that Madonna is also an extreme perfectionist, which has to be rough on the many assistants that she tends to hire. She even had a “food intake” assistant who was said to monitor every single thing she put her in her mouth (I will not make a joke here, I will not make a joke here…). The singer herself even joked about it during an interview with The Mirror. “I call her the food police,” she said. “Are you eating? Did you drink enough water?” I’m like, b***h, get off my pole!” So, you’re saying she hires people to get angry at when she can’t eat because she doesn’t WANT herself to eat? Okay, sure.

1 Keri Hilson

Celebrity Net Worth

While she was rising to fame years ago, the singer was faced with a pretty massive debacle when her assistant forgot to take off a store tag from the back of Keri Hilson’s pants before a performance. Hilson discovered the tag while performing on stage and apparently stormed off the stage in a heated rage and went after her assistant. She started screaming at the woman for “not being able to do anything right”. She even started screaming that the assistant forgot to “pack her eye drops and throat spray,” which then almost led to an full out brawl. Hilson’s bodyguard, and even her manager, had to intervene and break the two apart when the assistant stood her ground. No matter how famous anyone gets, they should never, ever treat the people who work for them with such disrespect. Karma has a way of coming back ten-fold with people like this.

Sources: femalefirst.co.uk, thehollywoodreporter.com, themirror.co.uk

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