Why being a celebrity assistant is truly the worst job in Hollywood

As a recruiter of personal assistants for celebrities and ultra-high net worth individuals – or to use his preferred term, “headhunter to the stars” – Brian Daniel is used to picking up his phone and finding a needy voice at the end of the line.

Traditionally, it’s been the household staff of an A-lister calling to ask if he knows somebody to be at the beck and call of their boss; or perhaps a billionaire CEO looking for a discreet and efficient young buck who’s particularly good at superyacht chartering, mistress management and administering threatening NDAs.

Daniel can handle all those, no problem. But lately, he says, the calls have taken on a different tone. “Did you know that in Japan you get such a thing as coaches to help you quit your job?” he asks, when we speak on a Zoom call.

“Well, a version of that has been going on in private service ever since the MeToo movement started. Because you’ve heard the stories about what was going on behind the scenes with Sean ‘P Diddy’ Combs, or Kanye West, or Scott Rudin, or Harvey Weinstein. It’s been slowly building over time...”

Last month, following the death of Friends actor Matthew Perry from “acute effects of ketamine” in 2023, his longtime live-in former assistant, Kenneth Iwamasa, pleaded guilty to one count of “conspiracy to distribute ketamine causing death”. The 59-year-old admitted to injecting Perry with the drug, including several times on the day he died. That charge could result in a 15-year prison sentence.

Daniel, who gives his age as “over 50” but confirms he lives in the Midwest with his young family after years in Los Angeles, has run the Celebrity Personal Assistant Network since 2007. For a decade before that he was a personal assistant to celebrities, billionaire businesspeople and foreign royalty.

“And you know what? Nothing comes close to the [Iwamasa] case. A huge shockwave has been sent through the industry. People are saying to me, ‘I want to get out of this life’ because they’re being confronted with things they don’t want to do. It chips away at you. It’s death by a thousand cuts, that’s what it can be,” he says.

Since the case against Iwamasa and other involved drug dealers – including doctors and the so-called “ketamine queen” – has been in the public eye, former assistants who served in similar roles have been divided on whether he should be punished for any wrongdoing.

Rowena Chiu, a former assistant to Harvey Weinstein, defended him. “When I read about Mr. Iwamasa’s indictment, I understood all too well that an assistant to a celebrity can be expected to do whatever is asked of them, regardless of ethics or legality… I’m not surprised that Mr. Iwamasa pleaded guilty,” she wrote in the New York Times.

Daniel is not on her side. “This guy was working with Perry for a while [around 25 years]. And that’s why it’s even more egregious. Yeah, you can get kind of scared and [the boss] makes you pee down your leg, but if you’ve worked with someone for that long, you obviously have a very deep personal and professional relationship with them. You’re the Pepper Potts to Iron Man, you know how to say no and when to say no. He should have been the one calling for help.

The Perry and Iwamasa incident was, he says, “a big disgrace.”

“It is the assistant’s job to be the gatekeeper and keep the wolves out of the hen house. I mean, he murdered Matthew Perry, essentially. He was the one pulling the trigger [...] He injects Matthew Perry, and then he leaves him in a hot tub and goes and runs errands? You can’t even write this stuff. This is going to be talked about for a hundred years.”

There are two things Brian Daniel recommends people do if they want to learn about his industry. “One, read my book. The Celebrity Personal Assistant Survival Guide, it’s free on my website. And two, if you haven’t seen the Whitney Houston and Kevin Costner movie The Bodyguard, you should see that right away because it is an absolutely accurate depiction of the posturing and the backbiting and the chaos and the insanity.” Julia Garner also brilliantly played the gruelling role of a Hollywood assistant in the 2019 film The Assistant.

The horror stories of celebrity personal assistants are legend, from allegations that Lady Gaga required her assistant to sleep in the same bed as her in case she wanted her film changed in the night, to claims that Katie Price made hers walk behind her dog so she could pick up its mess and that De Niro demanded back scratches.

Sean Combs once even hosted his own VH1 reality show, I Want To Work For Diddy, in which he challenged “13 determined young men and women with the raw potential to assist one of the most demanding CEOs in the world – Diddy.” The details of the now-unsealed indictment against Diddy have revealed just how “demanding” he really was. The eventual winner, Suzi Siegal, said earlier this year that she “felt sick and violently angry” after CCTV footage from 2016 of her former boss assaulting his girlfriend, Cassie Ventura, was made public. “Not one cell in my body was surprised.”

Legal action has become more common, in part, Daniel says, because smartphones have allowed assistants to “keep the receipts” and record any abuses with their camera or voice recorder, and in part because recruiters like him impress on candidates the importance of ironclad written contracts and work rights.

Despite so much bad press for the job, he’s seen no drop in new applicants. “In fact, the opposite is true.” Somehow a career in A-list servitude still holds an appeal, especially to young people drawn to a perception of glamour – even if the reality involves merciless 14 hour days, six days a week, the high possibility of a fickle employer and savage demands.

“Some people call it a servant’s heart. That’s from the Bible. But there’s something about serving people, right? And in my business it’s at a very, very high level.”

The pay is often dire, too. According to a 2021 survey by #PayUpHollywood, a grassroots support-staff organisation, 95 per cent of respondents said they make less than $70,000 a year, and 54 per cent less than $40,000, despite usually having to live in Los Angeles or New York. As a recruiter, Daniel insists clients pay assistants well into six figures, plus money to offer tips and open doors.

On top there is, he says, a particular thrill that can come with securing the best table at an impregnable restaurant with five minutes’ notice, or pleasing the world’s least grateful people. “And besides, with every bad story that’s out there, there’s two or three people who are with really good bosses.”

Daniel’s own career began as a personal trainer in Los Angeles in the mid-1990s, where he met the great and good of the entertainment and business industries in gyms. One client was a member of the Johnson & Johnson dynasty, who eventually asked him to become a personal assistant. From there, one job led to another, from Hollywood actors to becoming Chief of Staff to the Saudi Royal Family.

A model of discretion, Daniel has travelled the world and seen it all. The billionaire who had a secret sex dungeon in his basement. The unnamed high profile figure who neglected to reveal he was a nudist until his assistant rang the doorbell on her first day. The scions he’s had to “recover” from drug binges, essentially kidnapping them and flying them to residential rehab on behalf of their parents, without the media ever finding out.

The high profile cosmetic surgeon who invented a procedure “we all know”, who turned out to have a particular hidden quirk as a boss – namely that he was prone to bouts of domestic violence when he took lithium. The client who was so bad that Daniel excused himself to use the toilet one day, then promptly climbed out of the bathroom window and literally ran away from the job. And the “internationally known pop star” whose team specifically asked for somebody “who wasn’t a quote-unquote ‘celebrity assistant.’”

On that last one, Daniel knows that asking for somebody with no personal assistant experience is a red flag: more than most industries, assistants talk, relying on one another’s black books and experience for favours when they’re stuck trying to meet a ludicrous ask. Specifying that you’re looking for somebody outside of that network, then, is normally a sign that nobody from within would touch you with a barge pole.

“If you do anything connected to celebrities, you know this: celebrities are absolutely legendary for not paying their bills. Well, this person was asking their assistants to do crazy things, but the bills weren’t being paid. And that’s not worth it. It takes 20 years to build a reputation and five minutes to lose it.”

I say the name of a celebrity, quickly, hoping to catch him out. Daniel doesn’t flinch. “I cannot say who it was, but I did not take that job because, you know, my reputation.” It’s not a no.

Daniel runs vast background checks on all new clients and prospective assistants. Many VIPs only go to an agency when “they’ve burned through all their childhood friends and the neighbour’s nieces”, so he has them reveal every last skeleton in the closet of their personalities in advance. Invariably he fears for his rules – no drugs, no hidden addictions, no responsibilities to do with sex workers, no involvement in crime – and tells them he cannot help them.

It’s an industry that’s had to move with the times as much as any. And when a high profile case involving a celebrity assistant hits the news – whether it’s Lady Gaga, who was sued by Jennifer O’Neill for unpaid overtime in 2012, before the case was settled out of court – or Perry, there is a reaction.

“What inevitably happens is that everyone starts being on their best behaviour for a while, everyone tries to walk a straight line.” And then? “Then, over time, things start reverting back to the way they were.”

But he’s eager to stress the positives. Taylor Swift and Dwayne Johnson are, he’s heard, all terrific and generous bosses. And he was heartwarmed by viral social media footage last week of Beyoncé and Jay-Z attending the Nantucket wedding of her former assistant, Sam Greenberg. When the DJ played ‘Love On Top’, Beyoncé’s longtime bodyguard, Julius, tapped the bride on the shoulder and announced that the original artist would like to dance with her. Greenberg accepted. As you would.

It seems as if Beyoncé runs a good shop. “Yes, she does. There’s another story about her from years ago, where apparently she gave multi-million dollar bonuses to all her staff and crew after a particular tour,” Daniel says.

The fact Beyoncé’s fans knew everything about Greenberg in advance is another evolution in the industry: assistants to megastars now need to prepare to become the story. “The Kardashians did that. So many of their assistants [such as Stephanie Suganami, now an actor and entrepreneur with almost two million Instagram followers] have become celebrities in their own right. I can think of six or eight examples right off the top of my head.” Kim Kardashian, after all, began her career as Paris Hilton’s assistant.

Kenneth Iwamasa has now found himself the story too, only not in a way he’d have intended. Daniel wishes some good news stories about the industry he loves were heard more. The bad always represent “one step forward, two steps back.” He may be waiting some time.

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