These Are the Highest-Paid Celebrity Assistants in Hollywood, but Are Their Awful Bosses Worth It?

From an outsider’s perspective, celebrities have it easy. They’re richer than most people can imagine, they’re given opportunities many spend their lives working towards, and they’re constantly jetting off on vacation. Their whole existence seems like a breeze, but in reality, their daily lives require intense planning and scheduling. That’s where their personal assistants come into the picture.

Almost every celebrity in Hollywood has a personal assistant on their payroll. These assistants organize their diaries, answer their phone calls, manage their travel arrangements, and some are even tasked with smelling their armpits! And while some celebs pay their right-hand people a hefty sum for their hard and often bizarre work, there are others who expect the world for a measly wage. This is how much these celebrity assistants really get paid.

Kim Kardashian – Steph Shep (Estimated Salary $65,000)

Kim Kardashian is a woman who won’t stop, and it’s paid off. Kim started her own journey as a personal assistant to the stars, and now she’s one of the richest businesswomen in the world with a brand that spans across loungewear, skincare, and now private equity. From 2013 until 2017, she had Steph Shep by her side, helping her every step of the way. But Steph was so much more than just a personal assistant on a reported $65,000 salary.

Fans of Keeping Up With the Kardashians will know that Steph is also one of the whole Kardashian family’s BFFs. So, that’s why people were a little confused when Steph resigned from her post in 2017. But Kim was quick to squash any feud rumors, stating that “You guys, we’ve never had a feud. She wanted to go in a different direction. I respect that… Just because people stop working together, doesn’t mean that they’re feuding and stop being friends.”

Robert Downey Jr. – Jimmy Rich (Estimated Salary $62,000)

Robert Downey Jr. may have fans falling at his feet, but the actor likes to keep his circle small. That’s why he knew that he needed to keep his beloved personal assistant, Jimmy Rich, on his payroll for almost 20 years. Robert shelled out a reported $62,000 a year to have Jimmy as his assistant, and during their time together they also became best friends.

Jimmy started working for Robert in 2003, and he imagined them working together for the rest of his career. However, that dream was sadly cut short when Jimmy was involved in a fatal car crash in May 2021. Robert was devastated by the news, writing on Instagram that “He was a brother, my right-hand man, an uncle to our kids and beloved by all who experienced his singular character and wit.”

Brad Pitt – Lara Marsden (Estimated Salary $85,000)

Working as a personal assistant to the stars requires you to spend a lot of time with your boss. And while Lara Marsden was certainly up for the challenge, she didn’t anticipate that a wife would get in the way. She started working for the legendary actor Brad Pitt in 2011 and thought she’d hit the jackpot with her $85,000 salary. However, she was forced to quit just two years later under scandalous circumstances.

When rumors began to circulate that Lara and Brad were having an affair, all eyes were on his wife at the time, Angelina Jolie. Sources close to the couple stated that Angelina “was always jealous of Lara. She was always suspicious that there was something going on between Brad and Lara.” In the end, the rumors became all too much for the young assistant, so she decided to part ways with the actor.

David Bowie – Coco Schwab (Left $2 Million in His Will)

There’s a lot of fakery in the celebrity world, which is why famous faces often like to hire their friends as their personal assistants. This was the case for David Bowie, who hired his friend Coco Schwab to be his assistant in 1973. These two stayed together until his dying day in 2016, and Coco became his assistant, confidante, plus one, and even his savior. Yes, David claims that Coco saved his life on more than one occasion.

Unfortunately, their close relationship didn’t sit well with David’s ex-wife Angie Bowen – but that didn’t seem to phase David. He kept her as his right-hand woman for decades and knew that he would never have dreamed of having anyone else by his side. And while it’s not known how much David paid Coco as a salary, we do know that he thought so highly of her that he left her $2 million in his will.

Chris Hemsworth – Aaron Grist (Estimated Salary $75,000)

Like many other big-name celebrities, Chris Hemsworth is extremely busy. Whether he’s shooting a movie or a magazine cover, he needs someone to help him out – and since 2015, that someone has been his childhood friend Aaron Grist. Those who follow Chris on Instagram may already know that, as his assistant often makes hilarious appearances on social media. After all, these guys are buddies, too.

Chris reportedly pays Aaron $75,000 a year to be his personal assistant, but we have a feeling that there are also some more bonuses for being Thor’s assistant. In fact, for Grists’ birthday in 2021, Chris planned a surprise ’80s-themed birthday party that was full to the brim with celebrities. We don’t think many personal assistants can say that Matt Damon and Idris Elba came to their birthday party.

Meghan Markle – Amy Pickerill (Estimated Salary Unknown)

Meghan Markle’s life has certainly changed since she was on Suits. The former actress may have since stepped down as a working member of the Royal Family, but she’s still married to Prince Harry… which comes with some serious responsibility. Because of this, she utilizes the help of her very own personal assistant, Amy Pickerill.

Pickerill is no stranger to royalty, either. The 36-year-old English native used to work as a senior communications officer in the press office at Kensington Palace, working closely with the likes of Prince Harry, Prince William, and Kate Middleton. It’s now her job to help manage Meghan’s schedule, her official engagements, or to just hold flowers while Meghan’s busy. However, it’s not known how much she earns.

Britney Spears – Victoria Asher (Estimated Salary $70,000)

Throughout a huge chunk of her career, Britney Spears’ life and career was governed by her conservatorship. But when this conservatorship was terminated in 2021, she had free reign over her existence again – and this also allowed her free reign on who she hired to be on her team. It was during this time that she hired Victoria Asher to be her personal assistant, offering her a reported $70,000 salary in the process.

You might recognize this woman, too. Victoria Asher is perhaps best known as Vicky T, a keytarist who once played in the now-defunct band Cobra Starship. She started working with Britney last year, and they now seem to get on like a house on fire. Vicky follows Britney wherever she goes, and judging by Britney’s gushing posts about her, they’re way more than just employee and employer.

Martha Stewart – Kevin Sharkey (Estimated Salary $1 Million)

Celebrities often find it hard to trust people, which is why they choose to keep hold of the ones who prove they are worthy. That’s probably why Kevin Sharkey has worked for Martha Stewart for 27 years. The cooking and lifestyle guru hired Kevin back in the mid-1990s as her personal assistant, and they’ve stuck together through thick, thin, and an awkward stint behind bars.

Kevin’s devotion to Martha has certainly paid off… and in more ways than one. Not only is he paid an estimated $1 million per year, but with each passing year of service, Martha has given Kevin even more responsibility. Now, Sharkey has risen through the ranks and become the Executive Director of Design for Martha Stewart Living.

Beyoncé – Sam Greenberg (Estimated Salary $82,000)

Only a few select celebrities are able to make a name for themselves with just one name, and Beyoncé is one of them. This singer is an icon and known by almost everyone around the world… but she prefers to live a private life. She likes to keep her circle small and has focused her attention on finding a select few friends and staff members who have her best interests at heart. One of those people is Sam Greenberg.

Although not much is known about Sam Greenberg, we do know that she has been Beyoncé’s assistant since 2010, and is on around $82,000 a year. For that price, Sam maintains Queen Bey’s schedule, attends business meetings, helps her on the red carpet, and even helps out during studio sessions. In fact, Beyoncé thinks so highly of Sam that she credited her assistant on her Lemonade album.

Conan O’Brien – Sona Movsesian (Estimated Salary $100,000)

If you’re a fan of Conan O’Brien, you’ll probably know a lot about him. This comedian and talk show host isn’t shy when it comes to talking about his life or letting his fans into his world. That’s why many of his fans are already familiar with his personal assistant of almost 15 years, Sona Movsesian. And while Conan always likes to joke about Sona’s lack of motivation and bad work ethic, they get on like a house on fire.

Yes, these two are more like best buddies than employer and employee. And while Sona has even branched out and written a book called The World’s Worst Assistant, she can’t do too much of a bad job, as Conan pays her an incredible $100,000. Not only that, but this duo has become so famous they now even host their own podcast together.

Jeff Bezos – John Connors (Estimated Salary $125,000)

In September 2022, Jeff Bezos dropped down from second to become the third richest man in the world, but we have a feeling that he’s not too sad about that. With a net worth of around $147 billion, he’s certainly not short on cash. But that begs the question… why can’t be pay his assistant of 22 years a bit more than $125,000? After all, John Connors started working for the businessman in 2000, and has stuck by him through thick and thin.

Organizing the schedule of one of the world’s richest and busiest men can’t be easy, but John seems to do a pretty good job. Jeff even gushed about John in an Instagram post back in 2019, where he wrote: “John Connors has been my executive assistant for the last 19 years. He thinks ahead, sweats the details, and makes things fun… I want to say thank you. You’re a big reason I’m able to be so busy and not go nuts – in fact, you somehow make it calm. Thank you, John!”

Christian Bale – Harrison Cheung (Estimated Salary $0)

Christian Bale has no shortage of fans across the world. There are people who are absolutely obsessed with him and would jump at the chance to meet him or work for him – and Harrison Cheung was one of them. In fact, he loved the actor so much that he was willing to work as his personal assistant for nine years without getting paid a dime. In his words, he was just a “Canadian who loves movies” – but he probably wasn’t expecting to do what he had to do.

Harrison’s experiences of working as Bale’s personal assistant were so bad that he’s since written a book about his ordeal. He reported that he was treated cruelly by the actor, and was forced to do ridiculous tasks – like making emergency trips to the store for socks when the actor didn’t have any clean ones left, and even having to smell Christian’s armpits for body odor.

Rihanna – Jennifer Rosales (Estimated Salary $1 Million)

Rihanna may be a huge singing superstar, but she likes to keep her personal life private – which is why she’s extremely selective about who she lets into her circle. That’s probably why she’s also had the same personal assistant for over 15 years. Jennifer Rosales has been her right-hand woman through the thick of it, so it’s no wonder that Rhi Rhi is willing to shell out $1 million a year on such a wonderful asset.

However, these two are so much more than just work colleagues. Rhianna appointed Jennifer the Senior VP of Fenty Beauty as she thinks so highly of her, and Jennifer asked Rhianna to be her bridesmaid when she got married a few years ago. With all of the new developments in Rhianna’s life, we can assume that Jennifer also has a close relationship with the singer’s new baby.

Megan Fox – Madison Bigos (Estimated Salary $30,000 – $50,000)

Megan Fox is at the top of her game right now. The actress is not only starring in some of the biggest movies in Hollywood but she’s also an icon in popular culture – especially since she started dating Machine Gun Kelly. To help out on a daily basis, she has enlisted the talents of personal assistant Madison Bigos. It’s been reported that Megan pays Madison between $30,000 – $50,000 a year for her services.

While we’re sure that Madison works hard for her salary, online it looks as though these two are constantly having a ball. Madison travels with Megan wherever she goes, and on breaks in filming they’re always going ziplining, hanging out with tigers on safari, or just heading out for dinner. These guys look like they’re great friends, too.

Blake Lively – Jessica Snyder (Estimated Salary $55,000)

Blake Lively has been in the limelight for decades. Since starring in Gossip Girl she has gone on to achieve greatness as an actress, businesswoman, fashion icon, wife, and mother. And as you can imagine, she’s pretty busy. Thankfully, she has Jessica Snyder by her side for all of her wants and needs. And this lady is paid pretty well, with her salary estimated at around $55,000 a year.

However, it seems as though Jessica doesn’t just have a job… she also has a best friend. These two women have been through it all together, and so attending Jessica’s wedding just two days after she gave birth was a no brainer for Blake. For this occasion, Blake wrote on Instagram: “Most beautiful bride on the planet. And the best friend I could ask for. @jessicarose617 thank you for being EVERYTHING. I love you.”

Oprah Winfrey – Libby Moore (Estimated Salary $125,000)

You probably don’t need us to tell you that Oprah Winfrey has a busy schedule. She’s a talk show host, philanthropist, businesswoman, and so much more – and so she needs a competent aid to help her keep her schedule on lockdown. Between 2002 and 2013, that privilege was given to Libby Moore, who served as Oprah’s personal assistant. But Libby was more like a head assistant, when you think about it.

That’s because Libby was actually in charge of Oprah’s five other assistants, which meant that she had a huge amount of work on her shoulders. But she seemed to revel in the challenge. She explained to Women’s Agenda in 2017 that “I hit the job jackpot. It was like winning a Grand Slam. It was extraordinary and even now – five and a half years after leaving – it’s actually hard to articulate because it was so massive.”

Harry Styles – Emma Spring (Estimated Salary $50,000 – $100,000)

Long gone are the days of Harry Styles battling with his One Direction band members for attention. Today, he’s by far the most successful of the lot, and he’s since made waves with his solo music and even his foray into the world of acting. And with so many things on his plate, it should come as no surprise to learn that he needs an assistant. It’s reported that he pays Emma Spring anywhere between $50,000 and $100,000 – but he’s not like every other celebrity.    

While it’s Emma’s job to make sure that Harry is where he needs to be, when he needs to be there, their relationship has gone way beyond that. Harry trusts Emma so much that he made her the trustee of his $8.7 million condo in Manhattan, and she trusts him just as much. This was proven in 2014 when she let Harry take her baby out for a walk during a break in recording at a London studio.  

Tina Fey – Allison Williams (Estimated Salary $30,000 – $50,000)

Everyone knows Tina Fey as one of the funniest women in Hollywood, but what you might not realize is that she once had another famous face as her personal assistant. Yes, anyone who has watched Girls, The Perfection, or Get Out will be familiar with actress Allison Williams. And Allison’s very first job was serving as Tina Fey’s assistant. She reportedly earned between $30,000 to $50,000 for this role.

Their connection doesn’t end there, though. Before Allison started working for Tina, the comedian actually spoke about Allison’s high school graduation ceremony. During her hilarious speech, Tina reportedly gave the graduates two very important pieces of advice. The first piece of advice was to “wear a bra,” and the other was “don’t smoke.”

Kylie Jenner – Maguire Amundsen (Estimated Salary $90,000)

Despite all of the controversy surrounding Kylie Jenner’s “youngest self-made billionaire” title, there’s no doubt about the fact that 25-year-old Kylie is super rich. Not only is she a reality star and mother, but she’s also the founder of a billion-dollar makeup and skincare empire that just seems to be getting bigger and bigger every year. Since 2020, she’s had assistant Maguire Amundsen by her side to help her.

Kylie’s personal assistant is just as Instagram-happy as her boss, and it seems as though she loves her $90,000-a-year position. And from an outsider’s perspective, her assistant has both beauty and brains. After graduating from the prestigious Vanderbilt University with a degree in Organisational Development, Maguire went on to work in a talent agency and as the PA to American entrepreneur Brent Bolthouse.

Bill Hader – D’Arcy Carden (Estimated Salary $25,000 – $50,000)

Bill Hadar is a huge name in comedy, largely thanks to his impressive reign on Saturday Night Live. Like many other celebs in the world of show business, Bill has enlisted the help of an assistant to keep his work/life balance on track – and his former personal assistant was none other than The Good Place actress D’Arcy Carden.

In fact, D’Arcy was so much more than just a personal assistant. She also looked after Bill’s kids, receiving between $25,000 to $50,000 a year for all her hard work. It’s been said that Bill inspired her to really push for her dreams of becoming an actress, and helped her immensely along the way. Amazingly, she’s since worked alongside her former boss in his show Barry.

Elizabeth Taylor – Tim Mendelson (Estimated Salary $50,000 – $100,000)

As one of the most famous women Hollywood has ever seen, it should come as no surprise to learn that Elizabeth Taylor had a team of people around her. From makeup artists to housekeepers, she had a whole entourage. But it was Tim Mendelson she really put her trust in. He was her personal assistant for a whopping 20 years, and during that time she paid him anywhere between $50,000 and $100,000 a year.

This classic Hollywood actress loved her assistant so much that she made Tim the co-trustee of her estate, and it’s not hard to understand why. During her lifetime, Elizabeth went from working on one movie to the next, and it was even the same with her husbands. She married eight times before her sad passing, but Tim was the one constant in her life that she could rely on.

Ariana Grande – Doug Middlebrook (Estimated Salary $75,000)

Despite the fact that Ariana Grande may have millions of “Arianators” around the world who keep her online fan forums busy, the singing sensation likes to keep her personal life private. She has a small circle of friends who largely stay away from the limelight, and she even married a real estate agent rather than a big-name celebrity. That’s probably why her personal assistant is also one of her closest friends.

Doug Middlebrook is so much more than her assistant, though. He’s also her production and tour manager, and it’s down to him to ensure that Ariana is where she needs to be when she needs to be. But when they’re not working, they’re hanging out and posting silly photos of each other on Instagram. It’s pretty cool that Ariana also pays Doug a hefty $75,000 a year salary.

Khloe Kardashian – Alexa Okyle (Estimated Salary $70,000)

Even if you try to avoid the family, it’s hard to not know what the Kardashian family is up to. They’re constantly on television, walking red carpets, or promoting their latest business venture on Instagram. And Khloe Kardashian is no different. In order to keep her life as carefree as possible, she enlists the help of her personal assistant Alexa Okyle, who she pays around $70,000 a year.

It’s no secret that Khloe has suffered some tough blows with people she thought she could trust over the years, but Alexa has stuck by her side through it all and become a part of Khloe’s tight inner circle. She works closely with the reality star on a daily basis, and she’s even been promoted to the Director of Operations at Kardashian Jenner Communications in recent years.

David and Victoria Beckham – Rebecca Loos (Estimated Salary $75,000)

David and Victoria Beckham are one of the most famous power couples in the world, and they have been since they got hitched in 1999. During the early 2000s, they enlisted the help of personal assistant Rebecca Loos to aid in their everyday events, scheduling, and even their childcare. However, some say that Rebecca and David got a little too close and professional boundaries were blurred.

It’s estimated that Rebecca earned around $75,000 for her work as the Beckhams’ personal assistant, but that’s all she got – as she wasn’t asked to return after that first year. That’s because Rebecca sold a story to the press, claiming that she had been involved in an affair with her boss. David denied the claims and Victoria didn’t seem to think there was any truth in the rumor either.

Gwyneth Paltrow – Kevin Keating (Estimated Salary $85,000)

Although Gwyneth Paltrow is perhaps best known for her acting skills, she’s since put her acting career on the back burner to focus on her lifestyle company instead. Of course, Goop has raised major eyebrows since it launched in 2008, but it’s still a huge success. So, Gwyneth needs the right kind of people by her side, and that’s where Kevin Keating comes into play.

Those who have watched The Goop Lab on Netflix will already recognize this guy. Kevin is not only one of Gwyneth’s closest friends, but he’s also her “taskmaster” personal assistant. It’s his job to make sure her life and the company as a whole runs as a well-oiled machine, and it’s clear to see that he absolutely loves his job – not only for the $85,000 salary.

Paris Hilton – Kim Kardashian (Estimated Salary $30,000)

Before Kim Kardashian became one of the richest businesswomen in the world, she was just a young woman with a famous lawyer father. So, she had to try and make her own way up the ladder… and she did this by becoming Paris Hilton’s assistant. Kim stood by the heiress’s side from 2003 until 2006 on a $30,000 salary, but she doesn’t exactly like the word “assistant.”

During an interview with Andy Cohen on Watch What Happens Live, Kim preferred to call herself Paris’s “stylist” as her main job was to organize her closet, choose her outfits, and sell any clothes that Paris no longer wanted or needed. And while this probably wasn’t her dream job, working as Paris Hilton’s stylist certainly gave Kim a taste of the high life before she got there herself.