Pop superstar Ariana Grande hired Doug Middlebrook as a personal assistant many years ago, and the two have grown to become very close friends. This often happens when you trust your personal arrangements in the hands of someone other than yourself.
Doug was Grande’s date for the 2020 Grammy Awards, and he is also the voice you hear at the start of Grande’s hit song, “In My Head.” Apart from being her P.A., Doug is also a production and tour manager, meaning he’s the one who always makes sure Grande shows up for her events and keeps to her schedule.
Tamra Natisin – Katy Perry
Katy Perry has certainly made a mark in the music industry, becoming one of the most famous singers of the 2000s. Logically, a woman this busy needs an assistant, and Perry is lucky enough to have her best friend as hers. Tamra Natisin and Katy Perry were best friends long before Perry became an international celebrity.
Natisin was a production assistant for big Hollywood movies, and once Perry went big, she left her job and became her P.A. The two have been working together since 2008, and are still going strong. Natisin also dated star Kristin Stewart for a while.
Louise Leguen de Lacroix – Emma Watson
After skyrocketing to fame with her role in the Harry Potter film franchise, Emma Watson has steadily kept landing big Hollywood roles. And since 2007, her assistant Louise Leguen de Lacroix (who has one of the coolest, most noble-sounding names we have ever heard) has been right there by her side.
Lacroix is a professional event manager and schedule planner, while also holding a degree in Hospitality Management. These sound like the perfect skills for anyone in her line of work. Watson and she seem to have a fantastic work relationship and are still going strong even after all these years together.
Fiona Young – Kate Moss
The stunning Kate Moss is one of those high-profile celebs that have a great relationship with her assistant. Her P.A., Fiona Young, has worked for the supermodel since 2008, and the two are often seen together outside of working hours – shopping, attending events, etc. Just like in this picture.
Moss says Fiona is like a sister to her; she’s attended Young’s wedding and the birth of her child and has been there for important landmark moments. Sounds like an exceptionally close relationship! Her salary is unknown, but we suspect it has to be quite a hefty number to stick around for that many years.
Sam Greenberg – Beyonce
Working with Queen Bey has to be as exhausting as it is rewarding, and according to Sam Greenberg, that’s exactly how she would describe it. Since her time in Destiny’s Child, Beyonce has gone on to have one of the most successful solo careers in music history. But you already knew that. You'd have to be living under a rock to not have known that.
Since 2010, personal assistant Sam Greenberg has been by her side, witnessing Bey’s crazy work ethic and impeccable fashion taste. Apart from her grand salary, Greenberg is earning priceless inside knowledge of the music industry.
Theresa Marie Mingus – Selena Gomez
Singer and actress Selena Gomez has certainly come a long way since her Disney days. As the international superstar she’s become, she obviously needs a big staff working around the clock to help with her schedule. But no one is closer to the star than her best friend and personal assistant Theresa Mingus.
Mingus has been with Selena since 2014 and is not going anywhere anytime soon if this sweet Instagram picture of the two is any indication. Selena even promotes Mingus’s business — a swimsuit brand — all over her social media accounts. This is definitely a win-win relationship.
Rose Moon – Adele
Apart from having one of the best names ever, Rose Moon also holds the record for one of the best jobs in the world. Moon has been singer Adele’s personal assistant for more than nine years, and she could not be happier. Honestly, Adele seems like a hoot to be around.
Moon goes with the diva on her tours, events, and even day-to-day errands, and has said Adele is very kind and down-to-earth. Also, she’s said that Adele is a huge film buff, and the two of them often go to the cinema every time a new movie comes out.
Victoria Villarroel – Kylie Jenner
Victoria Villarroel is a model and social media influencer from Venezuela, and also Kylie Jenner’s best friend. But once upon a time, she worked as Jenner’s personal assistant – a job that lasted five years.
Even though Victoria quit in 2020 to pursue her own career, she and Kylie remain close friends. It must be quite a transition to go from being someone's personal assistant to having to employ one of your own. Good on you, Victoria! Of course, we imagine that the number of celebrity contacts that Kylie has hooked her up with must be coming in handy now.
Angel – George Clooney
Some high-profile celebrities have a constantly rotating staff, but George Clooney isn’t one of them. The acclaimed Hollywood actor has had the same personal assistant, Angel, for over three decades. Angel started working for the “Ocean’s Eleven” star in the 1990s after they met on the set of the popular TV show “E.R.”
As it turns out, Angel was working for Noah Wyle, Clooney’s co-star on the show, but it didn’t take long for the charming Clooney to win her over. We wonder if George ever refers to her as his guardian angel or if he's more original than that.
Patientce Foster – Cardi B
Patientce Foster started out as Cardi B’s close friend and publicist in 2017 and then added the title of “personal assistant” to her business card. Foster worked like crazy during the music star’s early career days, helping her achieve and handle the international fame she enjoys today. But after four years of non-stop work, Foster decided to call it quits in 2021.
As she explained in a magazine interview, “It became increasingly overwhelming and more difficult to accept that all of my invested time and energy, personal and professional sacrifices, resulted in no real equity or ownership.” That sounds fair.
Irving Milgrom – Hugh Jackman
Ever since his epic role as the Wolverine in the “X-Men” film series, Hugh Jackman has been landing big blockbuster roles. His assistant of the better part of two decades, Irving Milgrom, has made sure he keeps to his schedule and does his day-to-day errands.
Milgrom has been Jackman’s right-hand man on every movie set since 2009, and the two have naturally become close friends. It was bound to happen after so many years of working so closely with each other. In fact, Hugh affectionately calls him “Irv,” which we personally find quite endearing. We always love a good bromance.
Melinda Relyea – Sarah Jessica Parker
Melinda Relyea started working for “Sex and the City” star Sarah Jessica Parker in 1998, when the show was being filmed. On top of being her P.A. for several years, Melinda and Sarah became very close friends, with Sarah even being the bridesmaid for Melinda’s wedding. How sweet!
After her years as an assistant, Melinda moved on to production, becoming the producer for the two “Sex and the City” films that were made after the show’s finale. As if that was not enough to keep her busy, Melinda is also the VP of Sarah Jessica Parker’s production company, Pretty Matches.
Malia Obama – Halle Berry
Imagine having the president’s daughter as your personal assistant; this is what Halle Berry experienced when Malia Obama worked as her P.A. in 2014. Sounds like an incredibly thin tightrope to tread! On the one hand, you need your assistant to work for you, on the other hand, that means you will be bossing the president's daughter around.
The “Monster’s Ball” actress said it was definitely weird to have one of Obama’s daughters working for her, finding it hard to ask her to do things. However, Berry said she had a lot of respect for Malia because she was a hard worker and up to doing the tasks that any regular assistant would do.
Kevin Keating – Gwyneth Paltrow
Actress Gwyneth Paltrow was all over the silver screen back in the late 90s and early 2000s, but most recently, she has been known for her beauty and lifestyle empire, Goop. Needless to say, Paltrow keeps extremely busy with her business endeavors, acting career, podcast, and family, but thankfully, she has personal assistant Kevin Keating there to help her with it all.
Keating has been with the blonde beauty since 2010 and has become one of the Goop queen’s closes friends. In fact, you might have caught a little glimpse of Keating in Netflix’s “The Goop Lab with Gwyneth Paltrow.”
Alexa Okyle – Khloe Kardashian
Anyone who works for the Kardashians can definitely function under pressure, and handle a million things at once. These girls are some of the busiest bees in the entertainment industry. One of the superhumans who can handle them is Alexa Okyle, Khloe Kardashian’s personal assistant, who’s been with her for quite some time.
Not only has Okyle become one of Khloe’s closest friends, but she was also the first to know when the reality star got pregnant with True Thompson. Okyle has also worked for other Kardashian sisters and is currently the Director of Operations of Kardashian Jenner Communications. Well done!
Nichole Pellant – Jillian Michaels
American personal trainer Jillian Michaels has become quite the celebrity in the last few years. So logically, she needs a hand to keep things running (excuse the fitness pun, we couldn't help ourselves). Michaels hired personal assistant Nichole Pellant more than eight years ago, and the two are still working great together.
For someone like Jillian, that has a reputation for being harsh, Pellant is the perfect match. It seems she takes everything quite lightly, not paying too much attention to the fitness queen’s intense rants. We wonder if you have to be able to match Michaels to work for her.
Doug Middlebrook – Ariana Grande
Pop superstar Ariana Grande hired Doug Middlebrook as a personal assistant many years ago, and the two have grown to become very close friends. This often happens when you trust your personal arrangements in the hands of someone other than yourself.
Doug was Grande’s date for the 2020 Grammy Awards, and he is also the voice you hear at the start of Grande’s hit song, “In My Head.” Apart from being her P.A., Doug is also a production and tour manager, meaning he’s the one who always makes sure Grande shows up for her events and keeps to her schedule.
Sona Movsesian – Conan O’Brien
If you’re a fan of talk show host and comedian extraordinaire Conan O’Brien, then you definitely know who his quirky assistant is. Sona Movsesian has been Conan’s P.A. for over 13 years, and the two have even worked together on several projects. Ironically, a good portion of her public image is her not wanting to do any work.
Apart from assistant, Sona is also a writer, and she published a novel with a foreword from Conan himself (which is meant to be hilarious). With a salary of over $100,000 and a podcast with Conan, Sona has definitely done well for herself professionally.
Judy Ogle – Dolly Parton
‘Queen of Country’ Dolly Parton is more than a celebrity, she’s an American icon. This blonde sweetheart has been around since the late 50s, and she’s still being talked about. Right around the time her career blew up was also when she hired Judy Ogle, a friend she had known since childhood.
Ogle has been Parton’s personal assistant and friend since the 1960s, and amazingly, they are still working together! The two do everything together – events, meetings, family trips, you name it. Ogle is always by Dolly’s side and it seems like the two are as close as family.
Justine Ciarrocchi – Jennifer Lawrence
Since her role in “Winter’s Bone” in 2010, Jennifer Lawrence has steadily climbed the Hollywood ladder to become one of the world’s most famous and highest-paid actresses. But 2010 was also the year she hired Justine Ciarrocchi, her best friend, as her personal assistant.
Justine still works for Lawrence to this day and has stood by her through thick and thin. Imagine a job that was basically hanging out with your best friend all day. (Well, you'd also need to take care of her lunch orders and travel arrangements, but still.) Plus, we’re sure the $100,000 salary doesn’t hurt at all, either.
Kevin Sharkey – Martha Stewart
Martha Stewart has built an empire that needs a staff of hundreds to be kept running, but there is one person in particular that Stewart trusts more than anyone – her P.A. Kevin Sharkey. He’s worked for Stewart for more than 27 years and worked his way up to a salary of $1 million. That's what you get for sticking by Stewart for so long, people!
Sharkey stayed with the multimillionaire businesswoman through the worst times, and it was worth it. Nowadays, not only does he have a hefty salary, but he’s also the Executive Director of Design for the Martha Stewart Living brand.
Matt Harrell – Lindsay Lohan
Lindsay Lohan has definitely been through a lot, especially during the 2010s. Being her assistant could not have been an easy job, but her 5-year P.A. Matt Harrell survived it. Harrell was a loyal friend and assistant to Lohan in her darkest hours, staying with her through six spells in recovery institutions.
A very sad Lohan had to fire Harrell in 2014 because she could no longer afford to pay him. Still, Harrell stayed a while longer and helped her sort through all her belongings so she could sell and make some money off of them. Now that’s a true friend.
Betty Robin – Marilyn Monroe
It’s been more than 60 years since she passed, but people are still talking about Marilyn Monroe. Still, even though Marilyn was one of the most beautiful and famous women in the world at one point, she was actually very lonely. This fact was further confirmed by her personal assistant of ten years, Betty Robin.
Contrary to her sometimes outrageous demands on film sets, Marilyn was quite the opposite in her private life. Robin said the actress never really found true friends, often only surrounding herself with people who worked for her. It seems that back then, even more than today, it was nearly impossible to find an honest friend in this industry.
Tim Mendelson – Elizabeth Taylor
Elizabeth Taylor will forever be known as one of the most talented and glamorous women of Hollywood’s golden age. The “Cleopatra” star had a personal life that was as interesting as the roles she played, having been married eight times, each one with a considerable amount of drama.
There was one man that remained a constant through it all – her assistant Tim Mendelson, who worked for her for 20 years. Taylor trusted Mendelson so much that she made him a co-trustee of her entire estate, and Mendelson said the actress was the most loving person he’d ever met. He disclosed that the star wore diamonds around the house!
Jenna Dewan – Justin Timberlake
Everybody knows Jenna Dewan for her amazing dancing skills, which she showed off in “Step Up”, and her marriage to Channing Tatum. But before all of this, she worked as a backup dancer and P.A. to Justin Timberlake — a job that must have been pretty rewarding, even if it didn't gain her the same degree of publicity.
The former NSYNC member and Dewan even dated for a short while after Timberlake broke up with Britney Spears. Dewan only worked with Timberlake for a year, as she also did backup dancing for Mandy Moore, Ricky Martin, Janet Jackson, and Missy Elliott.
D’Arcy Carden – Bill Hader
You might recognize the name D’Arcy Carden as the co-star in Bill Hader’s TV show, “Barry.” But their relationship stretches far past that of co-stars. Long before "Barry" was even in the works, Carden worked as a nanny for Hader’s kids, with whom she has a close relationship to this day.
Apart from “Barry,” you might also recognize Carden from her role as Janet, the all-knowing being in the hit Netflix show, “The Good Place.” She’s also been an extra on "Saturday Night Live" during the time she worked for Hader, which was an impressive seven years. Great job, D'Arcy!
Kelly Engstrom – Karlie Kloss
American fashion model Karlie Kloss has worked with some of the world’s biggest fashion houses, meaning she has quite a hectic schedule. One of the thousands of assistants that have worked with Kloss is Kelly Engstrom, and even though she just lasted one day, she has good things to say about the supermodel.
Engstrom has worked with many A-listers and spilled some tea on the insane screening and vetting process that a P.A. goes through before getting the job. She said that Kloss was a particularly kind and nice person – an admirable quality when you’re one of the world’s most beautiful women.
Allison Williams – Tina Fey
Before she became a Hollywood celebrity herself, starring in “Girls,” “Get Out,” “M3GAN,” and more, Allison Williams worked as a personal assistant. Her boss was none other than genius comedienne Tina Fey, with whom she worked for five years. As you probably know, Fey is the woman behind some of the best pieces of comedy from the last couple of decades.
The two had a good working relationship, and Fey was even asked to speak at Williams’ high-school graduation. Surely, her $50,000 salary helped her save up during her college years before she was earning the hefty paychecks she makes today.
Rebecca White – Claire Danes
Rebecca White is one of those Hollywood assistants that has all the dirty gossip about her former employees. She has worked for Naomi Campbell, Lady Gaga, and a series of other A-listers. But back in the early 2000s, she worked for four years as Claire Danes’ P.A. White even dropped off the “Romeo and Juliet” star at college and helped her move in.
The two became quite close, with White having nothing but praise for the blonde actress. And why wouldn’t she? She had a salary of over $100,000 and lived for free in Danes’ $5 million loft in NYC.
Matthew Ryan – Kris Jenner
If you think that the Kardashian girls need assistants, imagine the actual Kardashian family matriarch who started the whole Kardashian empire, Kris Jenner. The Queen and socialite of reality TV has a team of dozens working around her constantly, but there is one particular guy that Jenner most depends on — her P.A. Matthew Ryan.
Ryan started working for Jenner in 2016, having had some previous experience with Hollywood royalty and the entertainment industry. The two are still working together, and it seems Ryan does great under pressure, which is a requirement to work for a woman like Kris Jenner.
Gilly Iyer – Jennifer Lopez
Gilly Iyer worked as Jennifer Lopez’s assistant for several years, becoming a close friend to the pop star. Unfortunately, and for reasons that remain unknown until this day, Gilly and Jennifer had a falling out that ultimately ended in Iyer resigning in 2013.
It sounds like the number one occupational hazard of trusting another person to manage another person's personal affairs. To make matters worse, Iyer immediately started working for Mariah Carey, who, according to the press, is J.Lo’s archnemesis. It seems the Latina diva didn’t make much of a fuss about it, as she hired another P.A. days later.
Jessica Labrie – Courtney Love
It isn’t surprising to learn that Courtney Love was sued by her assistant; after all, Kurt Cobain’s ex isn’t exactly known for being levelheaded. In 2010, Jessica Labrie started working for Love as her P.A. and was promised that her degree at Yale University (which couldn't have been cheap) would be completely paid for.
Two years, and a whole lot of drama later, Labrie sued the rockstar for unpaid wages. It seems she was never paid for any of her work, which included insane tasks – like being asked to falsify legal documents – which Labrie obviously refused to do.
Holliann Hartman – Taryn Manning
The “Orange Is the New Black” and “Crazy Beautiful” star Taryn Manning met Holliann Hartman in 2007 when she was working as her makeup artist. Similarly to the way you form a close connection with a person whose job requires close physical proximity (anyone poured their heart out to their hairdresser lately?), the two quickly became good friends, and Manning hired her as a personal assistant full-time.
Unfortunately, that didn’t last very long, as five years later, the two had a pretty bad fight. Even though details weren’t published, Manning was charged with assault and spent some time doing community work after being sentenced.
Cheyne Thomas – Miley Cyrus
Cheyne Thomas was Miley Cyrus’s assistant in 2010, and the two were as close as can be, elevating their relationship from the status of boss and worker to an actual friendship. The two girlfriends traveled, partied, shopped, and did everything together. In 2014, they even got matching tattoos as a sign of their forever friendship.
But all that came crashing down in 2016, when Cyrus got back together with Liam Hemsworth. Miley and Liam were known for the on-again off-again nature of their relationship. Nobody knows what happened at that specific time, or what caused the two friends to stop talking to each other. What a drama!
Terrence Smalls – Justin Bieber
Nowadays, you don’t hear much about pop superstar Justin Bieber, other than he’s married to the stunning Hailey Bieber. But a few years ago, this Canadian singer had a reputation for being particularly difficult to work with. Of course, a celebrity superstar like Bieber needs a right hand, and his was called Terrence Smalls.
He was Bieber’s assistant for two years and made an annual salary of around $70,000. However, Smalls was fired after he was caught in an Australian airport with 13 grams of an illicit substance. To boot, the police were also after Bieber since, apparently, he had nearly destroyed his hotel room after a night of partying. Yikes!
Bethenny Frankel – Kathy Hilton
If you google Bethenny Frankel right now, you will immediately notice what a powerhouse she is. Frankel is the founder and CEO of SkinnyGirl, an author of several books, a very successful businesswoman, a famous TV personality, and a known philanthropist. However, this wasn’t always the case; Frankel started out as a personal assistant to multimillionaire trophy wife, Kathy Hilton.
Frankel helped the hotel mogul’s wife with cooking, errands, picking up the kids, and more. She worked for Kathy for five years and made $100,000 a year, which she probably saved up for her future enterprises. The two remain friends, and nowadays, probably have a similar amount of money at the bank!
Laura Ramsay – Billie Eilish
Being a superstar starting in your mid-teens is no easy feat, which is why we’d probably forgive Billie Eilish for reportedly not being so nice to her staff sometimes. Maybe she will grow into the right manners. The chart-topping singer hired assistant Laura Ramsay in 2019, and they are still going strong.
With an annual salary of $50,000, Ramsay handles Eilish’s schedule, travel plans, day-to-day chores, and basically keeps her in check. People around the pop star have said that Ramsay has had a positive influence on the young singer, helping her assert control over her career and personal life.
Khloe Kardashian – Nicole Richie
Before she became one of the most famous media personalities and socialites on TV, Khloe Kardashian worked as a personal assistant for actress and fashion designer Nicole Richie. The two worked together for nearly five years, and Khloe had a salary of around $50,000.
Khloe and Nicole grew up together and were good friends, and as the Kardashian sister explains it, “Nicky needed help, and I needed a job, so I helped!”. But shortly after, “Keeping Up with the Kardashians” blew up our televisions, and none of the Kardashian girls ever had to work menial jobs again. In fact, they employ assistants of their own now.
Emma Spring – Harry Styles
Apart from his insanely hectic schedule, Harry Styles was also very young when he became one of the world’s biggest celebrities. That means he needs someone who is both experienced and can command logistics like nobody's business. The former One Direction boy needed help, and that came in the form of personal assistant Emma Spring.
The British pop star and Spring have worked together for over eight years, and she has a hefty salary of $100,000. But Spring is not just a P.A.; she’s also founded her own record label and is apparently one of the “human beings I most trust in the world,” says Styles.
Libby Moore – Oprah
As far as celebrities go, there probably isn’t a better person to work for than the beloved Oprah Winfrey. In 2002, Libby Moore landed the coveted gig of being Oprah’s chief personal assistant, which meant that, apart from her own tasks, she had to manage a small army of five other junior assistants.
Apparently, things went well, because Moore stayed on for eleven years, becoming Oprah’s close friend. In 2017, five years after leaving the job, Moore still got emotional when saying it had been one of the best jobs she would ever have. And with a salary of $125,000, we believe her.
Michael Doven – Tom Cruise
Back in 1992, when celebrity superstar Tom Cruise was filming “Far and Away,” he met one of the set assistants — Michael Doven. Cruise was so impressed with his work that he offered him a job as his personal assistant and his life changed forever. Doven obviously accepted the offer and worked with Cruise for 12 years.
With a salary of $80,000, Doven helped Cruise with everything from personal errands to travel plans, work schedules, day-to-day tasks, and basically anything you can imagine. In fact, Doven was the star’s right-hand while filming “Minority Report” and “Mission: Impossible.” Now that’s a CV!
Jessica Snyder – Blake Lively
It isn’t surprising to learn that the stunning and talented Blake Lively is as sweet in real life as she appears to be in her acting roles. Lively skyrocketed to fame with her role in the hit show “Gossip Girl” back in 2000. With increasing job offers and a growing family, Lively needed help, so she hired Jessica Snyder. The two became like sisters.
In 2016, Lively went to Snyder’s wedding just 48 hours after giving birth and posted a photo of her and Snyder, with the caption, “Most beautiful bride on the planet. And the best friend I could ask for. Thank you for being EVERYTHING. I love you.”
Kasi Brown – Leonardo DiCaprio
Since the 1990s, Leonardo DiCaprio has become one of the most famous and talented actors in Hollywood history. With a career spanning three decades, it’s only fitting this heartthrob would have several assistants over the years. But one that he dearly remembers is Kasi Brown.
Brown started working for DiCaprio in 2003 while he was shooting “The Aviator,” and she became his personal assistant for nearly two years. Brown said that Leo was kind, smart, and a genuinely down-to-earth guy. And apparently, he’s quite hilarious. With a salary of $100,000 and a boss like that, Brown definitely hit the job jackpot.
Madison Bigos – Megan Fox
The jaw-droppingly beautiful Megan Fox broke out on the silver screen in the early 2000s with the Transformers franchise, and she’s been getting constant work ever since. You might also remember her from her roles in films like "Jennifer's Body" or the latest installments of "Teenage Mutant Ninja Turtels."
For the last few years, Fox’s right hand has been assistant Madison Bigos. Fox hired Bigos in 2019 and has cemented a close relationship with Bigos being her P.A. on “Till Death,” “Big Gold Brick,” “Taurus,” and others. Bigos makes $50,000, and Fox gets her life organized and everything done on time. It’s a win-win.
Angelica Castillo – Sharon Stone
The “Basic Instinct” star Sharon Stone has a marvelous career under her belt. What she doesn’t have is a good reputation when it comes to employees. In the mid-2000s, Stone hired Angelica Castillo as a housekeeper and personal assistant, and the two seemed to be getting along, at least until 2013.
Stone and Castillo had a massive falling out when Castillo sued her for damages, claiming that the movie star forced her to work when she allegedly had a note from her doctor to stay in bed for weeks due to severe back pain. Unfortunately, this isn’t the first time Stone has been sued by an employee.
Jennifer Rosales – Rihanna
Leave it to RiRi to have an incredibly good relationship with her personal assistant; how could she not? The woman is a sweetheart. Rihanna hired P.A. Jennifer Rosales over 15 years ago, and they’re still working together, even throughout Super Bowl halftime shows, pregnancies, tours, and multiple new business enterprises. It looks like nothing can come between the two.
Nowadays, Rosales has a salary of a hefty $1 million and is not only Rihanna’s closest friend but also the Senior VP of the pop star’s iconic beauty brand, Fenty Beauty. Rihanna was even a bridesmaid at her wedding! We hope the bride wasn't overshadowed.
George Jacobs – Frank Sinatra
Even blue-eyed crooners like Frank Sinatra needed assistants – perhaps even more than present-day celebrities do. Sinatra’s right-hand man for over 15 years was George Jacobs, a man that started out as a valet for one of Hollywood’s most famous agents in the 50s. In 1953, Sinatra hired Jacobs, who, apart from his P.A. role, became his confidant and friend.
Sadly, in 1968, Jacobs was fired after Sinatra heard he was dancing with his then-wife, actress Mia Farrow. In a memoir about his years with Sinatra, Jacobs claims it was all a misunderstanding. Guess we’ll never know. Though we are curious.
Crystal Robinson – Usher
With a salary of $100,000 and over six years on the job, Usher’s assistant Crystal Robinson isn’t likely to quit her post anytime soon. We can't think of anyone who would, to be honest. Currently worth over $180 million, Usher started his music career when he was in his early teens.
His mother enrolled him in singing competitions, and soon enough, the talented singer got scouted, and the rest is history. Robinson has been his right-hand woman for a while now, and reportedly, Usher doesn’t go anywhere without her. This sounds like a healthy employer-employee relationship if you ask us.
Tracy McNew – Eminem
Since his “Slim Shady” LP came out in 1999, Eminem has become one of the biggest and wealthiest rappers in the world. Not surprisingly, he walks around with an entourage, providing jobs for a full staff of people – bodyguards, managers, you name it – and one of his most trusted is his personal assistant, Tracy McNew.
McNew has been by the rapper’s side for over 14 years and currently earns a reported salary of around $150,000. Eminem and McNew have become so close that there have even been rumors of the two dating, which they have, of course, denied.
Melissa Rooker – Clint Eastwood
The dashing Clint Eastwood has been a Hollywood staple since the mid-60s when he began starring in Sergio Leone’s spaghetti westerns and became known as the “Man with No Name.” Since then, he has starred in some of cinema’s most famous classics. Eastwood has four Academy Awards and four Golden Globes under his belt and, apparently, is a joy to work with, according to Melissa Rooker.
Rooker was Eastwood’s assistant for over 15 years; she read and analyzed potential scripts, helped him with his production company, and did everything in between. She retired with a hefty savings account in 2001 to spend more time with her family.
Renegade Piranha – Snoop Dogg
Leave it to Snoop Dogg to have an assistant whom he pays a salary of $50,000 to roll his special cigarettes. The lucky woman, Renegade Piranha, is a professional roller and has been rolling for the famous rapper since 2016. We had no idea people could roll for a living!
Since 1992, Snoop Dogg shot to stardom with hits like “Gin and Juice” and “Drop It Like It’s Hot” and continues to be legendary in the hip-hop world. His recent cooking show with Martha Stewart is as hilarious as it is strange, and hey, the man is definitely too busy to roll his own stuff.
Bob Halley – Elton John
One of the world’s most famous musicians and most glamorous rockstars, Elton John, has been gracing us with his music since the early 70s. Of course, it is to be expected that a man like him would need a dedicated personal assistant, which he had in Bob Halley. Halley worked for Elton for 30 years, practically his entire adult life.
Unfortunately, in 2008, they had a falling out, and Halley left his job of three decades. In a crazy turn of events, it appears Halley had been a close friend to Elton’s mother, who left him her entire fortune when she passed in 2018. Drama!
Lianna Shakhnazaryan – Mariah Carey
Mariah Carey’s vocal talent is undisputed – her five-octave range has earned her the nickname “Songbird Supreme,” and she’s been topping the charts since the early 2000s. But apparently, the “All I Want for Christmas Is You” singer doesn’t have a good track record when it comes to keeping employees.
Her former assistant, Lianna Shakhnazaryan, only lasted two years and was abruptly fired after Carey claimed she had violated the NDA clause in her contract and filmed intimate videos of Carey. But the drama didn’t end there, as Lianna sued Carey back and said she’d suffered harassment and battery while working for the diva.
Lauren Weisberger – Anna Wintour
Remember the film “The Devil Wears Prada”? Well, it was based on this personal assistant’s account of working for the legendary editor-in-chief and artistic director of "Vogue" and "Condé Nast," Anna Wintour. Lauren Weisberger went to Cornell, and when she graduated in 1999, landed a job as a P.A. in Vogue.
She worked for Wintour for exactly 11 months and had a junior salary of $25,000, but her biggest takeaway was the book deal she landed after. Weisberger wrote a revealing account of her time working for Wintour, sold it to publishers for a quarter of a million dollars, and then got a movie deal. Apparently, when Wintour was asked to comment, she couldn’t even remember who Weisberger was!
Kim Kardashian – Serena Williams
Before she became one of the world’s most famous socialites and celebrities, Kim Kardashian was a personal assistant. Yes, you read that right – Kim was a P.A. for none other than tennis legend Serena Williams. Apparently, this is how their close friendship relationship started in the first place.
Kim was hired by Serena to organize her closet, which reportedly is one of Kim’s most amazing skills. In fact, in the mid-2000s, Kim was known as the “Queen of the Closet Scene” and worked for several celebrities. Nowadays, she probably has three assistants of her own to arrange her closet.
Stephen Eads – Bruce Willis
Now, this is a relationship for the ages – Bruce Willis and his assistant Stephen Eads have been together for over 30 years. Though he has three siblings of his own, it seems that Willis and his assistant are like brothers. The “Die Hard” star has had Eads by his side since the early 90s, seeing him through some of the biggest moments of his career.
More than a personal assistant, Eads has even produced some of Willis’s films. Apart from a stellar career, Eads earned a lifelong friend. And an impressive salary of half a million dollars, of course.
Ana Charlotiaux – Angelina Jolie
If there’s one thing you should never do, is have a falling out with your assistant. This is exactly what Angelina Jolie learned in 2008. The gorgeous “Tomb Raider” star hired Ana Charlotiaux to help her and Brad Pitt when they were living in their famous Chateau Miraval in France.
After two years of working for Jolie, Charlotiaux, whose job was little more than answering phone calls and emails, got fired by her boss for taking too many sick days. Charlotiaux sued Jolie for ‘wrongful dismissal’ for the amount of $67,000 and gave every major publication detailed accounts of her time working for Jolie and Pitt.
Tony Dennis – Ozzy Osbourne
Ozzy Osbourne started his incredible career in the 1970s, first as the lead singer of Black Sabbath, and then as a solo artist. But even the “Prince of Darkness” needs an assistant, and for Ozzy, that’s been Tony Dennis, who’s been his right hand for over three decades of shows, tours, bat heads, and general Ozzy shenanigans that most of us can only dream about.
Dennis started working for Ozzy in 1983 and was basically portrayed as a family member in the 2002 reality TV show “The Osbournes.” Even though their working relationship ended in 2014, they remained very close.
Janey Bergam – Keanu Reeves
Keanu Reeves has always been one of those celebrities that likes to keep out of the spotlight. And his career speaks for itself, considering he’s starred in some of the biggest blockbusters in the last decades, including “Speed,” “Matrix,” the “John Wick” film series, and dozens of others. But this handsome leading man also needs help to keep up with his busy schedule.
Back in 2008, when he was shooting the sci-fi film “The Day the Earth Stood Still,” his personal assistant, Janey Bergam, was right by his side. Bergam and Keanu had a great working relationship for many years, even remaining close friends after she left.
Harrison Cheung – Christian Bale
Christian Bale is undoubtedly one of the best actors of our time and, apparently, one of the hardest to work for as well. According to Harrison Cheung, Bale’s personal assistant for nearly a decade, he wasn’t paid a cent for all his hard work.
After finally calling it quits, Cheung wrote a memoir about his time with Bale, and the book “Christian Bale: The Inside Story of the Darkest Batman,” is quite hard to read. Cheung says he was often asked to smell Bale to make sure he didn’t have any B.O. and get him clean socks and underwear when the star needed them. Yikes!
Robyn Crawford – Whitney Houston
This diva needs no introduction, as you’d be hard-pressed to find someone that doesn’t know (and love) Whitney Houston. She’s sold millions of records, topped hundreds of Billboard charts, and apparently, was also an amazing human being in her personal life. As documented by her personal assistant of more than 20 years, Robyn Crawford, Houston is an admirable woman.
Crawford stayed by Houston’s side through thick and thin – fame, substance dependencies, secrets, and everything in between. In her memoir “A Song for You,” Crawford tells the whole story of her life with Whitney, who left us way too soon.
Jennifer O’Neill – Lady Gaga
No one really knows who music celebrities are off the stage. But Mother Monster’s personal assistant, Jennifer O’Neill, got a crash course, and not necessarily a good one. During the two years she worked for Gaga back in 2009, during the Monster Ball tours, Jennifer claimed she did seven thousand hours of overtime, for which she did not receive compensation.
Also, she apparently had to sleep in her boss’s bed often for emotional support and give her medicine every day – with a salary of just $75,000! Jennifer ended up suing Gaga for nearly $400,000 and even wrote a tell-all book about the star.
Melissa Toubati – Meghan Markle
When you imagine being Meghan Markle’s personal assistant, few happy thoughts come to mind. You would think that handling the schedules and arrangements of an actress, a duchess, a mother, and a general person of interest would be a special kind of hell, and you wouldn’t be wrong.
Back in 2018, Melissa Toubati was the Duchess of Sussex’s P.A., but she quit after a short six months. Even with a salary of $80,000, Melissa said the job was way too stressful, and she often ended the workday in tears. It seems Miss Markle is a bit too demanding and anxiety-inducing.
Colin J. O’Hara – Matt Damon
Back then he had no idea, but taking on the position of a production assistant in the first film in the Bourne franchise changed life forever for Colin J. O’Hara. Starting off as a production assistant for the hit blockbuster “The Bourne Identity,” the man transitioned into Matt Damon’s personal assistant in 2002.
Things seem to be going well because the two are still working together. Colin manages Damon’s shooting schedule, day-to-day commitments, meetings, events, etc. In fact, he was by Damon’s side during the entire “Bourne” film series and every movie the actor has starred in ever since. Now that’s commitment!
Aaron Grist – Chris Hemsworth
It seems the Australian heartthrob Chris Hemsworth is not only gorgeous but also a sweetheart. According to his personal assistant, Aaron Grist, who’s been with the actor since 2015, Chris has become a very close friend. Hemsworth even threw him a massive birthday party once, with an 80s theme, and a guest list that featured Hollywood’s most famous celebs.
And judging by the dozens of photos they keep posting regularly on social media, it doesn’t seem Grist has plans to leave his job with “Thor” anytime soon. And honestly, with his film career and family of five, Hemsworth sounds like he definitely needs the help.
Coco Schwab – David Bowie
Now, this is an assistant story for the books. Back in 1973, Coco Schwab answered an ad published by David Bowie’s management company – the rockstar needed a personal assistant, and she needed a job. As it turns out, Coco ended up working with Bowie for 46 years, until his passing in 2016.
Coco and David became like family; she saved Bowie’s life many times, helping him with his substance dependencies, severe depression, and the worst parts of the rockstar’s life. Bowie said in an interview once that he wouldn’t have made it without her. When he passed, he left Coco $2 million in his will.
George Koehler – Michael Jordan
You’d think that being one of the world’s most famous athletes, Michael Jordan wouldn’t have time to befriend anyone but his teammates. But as it turns out, the greatest basketball player of all time has a best friend, and it’s his personal assistant George Koehler.
Jordan met Koehler when he was working as his limo driver back in 1992, and the two have been inseparable ever since. In fact, many say that Koehler is one of the few people that can handle MJ’s tough character and super-competitive attitude head-on. He must be one special guy to have that kind of stamina.
Odessa Whitmire – Ben Affleck
Being Ben Affleck’s assistant if you were a woman was probably quite difficult during the time he was with Jennifer Lopez. No one would want to deal with a jealous J.Lo, and actually, that’s exactly what happened to P.A. Odessa Whitmire back in 2002.
After just a year of working for Affleck, Odessa was basically living in the star’s house, and Lopez didn’t approve of that one bit. So, in 2003, Whitmire was let go. Fun fact: Affleck’s best friend Matt Damon was dating Odessa for a while, and things even got serious for a while, but ultimately ended, also in 2003. Not a great year for Odessa.
Lara Marsden – Brad Pitt
From 2011 to 2013, Lara Marsden worked as Brad Pitt’s personal assistant, and everything was going well until the press started hounding her. Why? Because they thought she and Pitt had become an item. Apparently, you can't be a female in the presence of Brad Pitt without people suspecting you having anything romantic going on.
Marsden claims that it was Angelina Jolie that started the rumors so she would get unwanted attention from the press. Many say that Jolie was jealous of her and had motives to make Lara resign, which she ultimately did. Oh well, at least she saved some money from her $85,000 salary.
Michael Davidson – Nicolas Cage
Since the late 1980s, the great Nicolas Cage has been gracing our screens with masterpieces like “Leaving Las Vegas,” “Raising Arizona,” “Lord of War,” and dozens of others. We imagine that working with Cage must be quite a ride — both highly entertaining and intense. Not to mention, working with him throughout all this time probably also means one would have to know at least three of the actor's wives.
It seems that his assistant of more than 13 years, Michael Davidson, agrees with this. Davidson has been by Cage through the making of some of his highest-grossing movies, including “The Sorcerer’s Apprentice” and “National Treasure.”
Vanessa King – Julianne Moore
The incredibly talented and gorgeous redhead Julianne Moore is a true master of her craft. The “Boogie Nights” star has been in countless blockbuster films, as well as in smaller independent projects, and everything in between. And it seems she’s also a sweetheart in real life.
Her personal assistant, Vanessa King, has been with Moore for over 16 years and has since branched out to help more than just Julianne, who sometimes shares King with her husband. So yeah, she also assists Moore’s husband, director Bart Freundlich, with scheduling and travel plans. Moore's family has described her as the “mission control” of their home.
Jimmy Rich – Robert Downey Jr.
Despite being a phenomenal actor, Robert Downey Jr. has earned himself quite the “bad boy” fame due to his chaotic personal life. There were issues with him using various legal or semi-legal substances and his journey to recovery was far from easy. His assistant, Jimmy Rich, has seen it all.
Working with Downey since 2003, Rich saw the actor through the worst of times, helping him with his career and image. Tragically, Rich passed away from a car accident in 2021, and it took a heavy toll on Downey. The actor withdrew from the spotlight for some time to mourn.
Rebecca Loos – David and Victoria Beckham
A celebrity’s worst nightmare is for their personal assistant to go rogue, and that’s exactly what happened to Victoria and David Beckham in 2003. In need of an assistant to help them out with the numerous things that have on their plate, the famous couple hired Rebecca Loos, and for a while, everything was going great.
Until Loos decided to go to the press claiming she’d had intimate relations with David. The press went crazy, and for a while, it was all you could read in the news. The Beckhams denied the rumors and tried to go back to their normal life, which they eventually managed to do.
Chris O’Dell – The Rolling Stones
Making history for becoming one of the first female tour managers in the music industry, Chris O’Dell has worked with the most legendary rockstars, including great names like The Beatles, Bob Dylan, and The Rolling Stones. O’Dell started working as a personal assistant for The Rolling Stones back in 1972, going on every tour and living their wild rollercoaster lives.
In fact, many people claim she’s the “mystery woman” from the Stones’ album “Exile on Main Street.” She’s also good friends with Yoko Ono and was there for the recording of “Abbey Road,” “The White Album,” and “Let It Be.”
Kathy Battaglia – Tiger Woods
Tiger Woods is one of the most famous athletes in history, both for his skills and his personal life dramas. This guy has enough going on in his life to employ a hundred personal assistants but Kathy Battaglia held that position all on her own. Battaglia, Wood's personal assistant of nineteen years, was there for it all.
However, after nearly two decades of loyalty, Battaglia quit in 2020. This was also around the time that his longtime PR manager left him too. It seems whatever happened wasn’t worth keeping the $150,000 salary. Now that’s a story we’d love to hear.
Ann Hiatt – Jeff Bezos
For 20 years, Ann Hiatt worked as Amazon CEO and billionaire Jeff Bezos' executive assistant and executive business partner. She was also the right hand of many Silicon Valley kings, such as Google’s CEO, and other multimillion tech companies. While not very famous to non-techies, she can probably take credit for a substantial piece of today's technological progress.
Throughout her two-decade career with Bezos, Hiatt became an investor, executive consultant, author, and tech strategist. Hiatt amassed enough knowledge and contacts to branch out on her own as a strategist for other companies and currently lives a very luxurious life in Europe.
Amie Castaldo – Naomi Campbell
Everyone knows the gorgeous supermodel Naomi Campbell, who became one of fashion’s most famous names in the 90s and still walks high fashion runways even now. What most people don’t know, however, is that as sweet as this supermodel appears in the media, she’s been sued more than once for alleged mistreatment of her employees.
Back in 2004, Campbell hired Amie Castaldo as her personal assistant, but it wasn’t long until Castaldo sued her for emotional abuse. Apparently, Campbell became enraged over simple things like not being able to go to her favorite hair salon. People are still talking about it!
Stephanie Shepherd – Kim Kardashian
Socialite and reality TV star Kim Kardashian is one of those celebrities that probably has a team of hundreds. Unless we're talking about physical things like taking a shower, she can probably employ anyone to do anything. Back in 2013, one of the most important people on her staff was her personal assistant Stephanie Shepherd.
The two worked together for four years, during which Shepherd also became COO for Kardashian West Brands. For unknown reasons, Shepherd left Kardashian’s side in 2017, and the rumor mill claimed they’d had a huge fight. However, Kim quickly spoke out, saying that no such thing had happened and “Steph just wanted to go her own way.”
Victoria Asher – Britney Spears
From her days as the world’s most famous pop star in the early 2000s to her highly publicized conservatorship matter, we’ve all followed Britney Spears’ crazy life. The pop star hasn’t had it easy, which is why her millions of fans were very happy to learn she’d hired Victoria Asher as a personal assistant in 2021.
Spears seems to be getting along very well with Vicky, posting constantly on her social media accounts. Whatever Victoria is doing, it’s keeping Spears happy, so we’re all for it. If anyone in the industry absolutely must be surrounded by people who make them happy, Spears is most definitely that person.
Mary Beth Brown – Elon Musk
Judging by what we see in the media, working for Elon Musk must be no picnic. However, there’s one woman that managed to swing it for over 12 years – Mary Beth Brown. She worked the same hours as her boss, which often meant staying awake for 24 hours in a row.
For many years, Brown had a salary of $60,000, and when she dared to ask for a raise in 2014, Musk asked her to take some time off so he could think about it. Two weeks went by, and Musk fired Brown, simply telling her that while she was away, he realized he didn’t really need her.
Carline Balan – Jay Z
Probably the closest person to one of the most influential families in the world, Carline Balan hit the jackpot when she started working for rapper Jay-Z back in the 90s. Balan has been a loyal personal assistant to Jay-Z and Beyonce for over 20 years and has even founded her own lifestyle company thanks to her savings and connections – Balan, Inc.
Balan is not a one-gal staff as Jay and Queen Bey obviously have one of the busiest agendas in the world. Apart from her $100,000 salary, Balan is one of 80 employees that work for the superstar couple that received 50K bonuses from their very generous employers.