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The efforts Hollywood assistants have to make for their bosses

Job postings for assistants rarely list duties that include administering illegal drugs to the boss, sharing a bed or tolerating physical advances that district attorneys classify as rape.

Nor do they warn that the contestants' lives are dominated by needy superstars who regularly test the moral boundaries of those around them. But such is the fate of celebrity assistants.

Consider the afternoon of October 28, 2023, when Kenny Iwamasa, who worked as Matthew Perry's live-in assistant, injected the Friends star with a lethal dose of ketamine.

Iwamasa recalled the last words he heard from his boss – “Shoot me a big one” – as he was harassed by police after his arrest. He pleaded guilty to conspiracy to distribute ketamine. Perry died while floating in his backyard hot tub.

Matthew Perry begged his assistant to inject him with ketamine. This is one of the most unpleasant tasks a celebrity assistant has to do. Los Angeles Times via Getty Images
Kenny Iwamasa sometimes had to inject Matthew Perry with drugs. Other times he took him shopping for sports equipment. Jeff RAyner/Coleman-Rayner

“My first reaction is that it's heartbreaking on many levels,” former celebrity assistant Merryl Futerman, author of the novel “Don't Make a Scene: Struggles of a Celebrity PA,” told the Post. “But I'm also aware that the role of personal assistant is a gray area. That concerns what you can do and how you can't not do things, how hard it can be to say no.”

Speaking to the Washington Post, a veteran Hollywood executive agreed: “You can't say no. When Matthew Perry tells you he needs a refill, you understand him. He helped him get what gets him through the day. Now the least powerful person” – one without access to the expensive lawyers and PR people who can protect celebrities – “has been arrested and pleaded guilty.”

Of course, keeping his boss's drug use a secret was also of paramount importance. Iwamasa's Linkedin profile lists his best qualities at the top: “I am discreet, loyal and maintain absolute confidentiality.”

The arrest of the 60-year-old from Midland, Michigan, is said to have taken friends and family by surprise.

Briana Brancato was described as the late actor's best friend.

Not all of Perry's assistants had it so tough. Briana Brancato was also employed by him. According to her Instagram and his book “Friends, Lovers and the Big Terrible Thing,” his main duties included lounging by the pool and being Perry's best friend.

Former star assistants and entertainment industry insiders told the Washington Post that the life of a star assistant is actually a mix of glamorous living, distance from the intoxicating world of Hollywood stardom and the pressure to do reprehensible things.

“It's a tricky business,” one Hollywood star told the Washington Post. “You're asked to do something unethical, but you don't want to lose your job, and the star makes his assistant feel obligated to do it. I've seen celebrities have their assistants carry drugs through the airport. Some assistants go to extremes.”

One top producer told the Post that “saying no” is generally not an option for someone who wants to stay in the employ of an arrogant superstar. When they are demanding, he said, “it is very hard. And sometimes [the celebrity] is abusive. You either have to accept it or look for another job.”

Stars can console themselves with the fact that assistants are dispensable: “It is not difficult [to find a new one],” the producer continued. “People want these jobs.”

Kenny Iwamasa described a job as one that many people want to have. APEX / MEGA
Author and former personal assistant Marryl Futerman finds Matthew Perry’s death “heartbreaking on many levels.”

Even more critically, they want a new job. In a recent New York Times op-ed, Harvey Weinstein's former assistant Rowena Chiu wrote that Weinstein “tried to rape me.” She added that Weinstein could fire her “on the spot” and that another job in the film industry was out of the question. “The blacklist was permanent.”

However, assistant salaries can help make things feel bearable. The producer estimates that a full-time assistant can make $150,000 a year. Whether they live with the boss or not, enough perks – like fine restaurant meals, car transportation and private jet travel – are included in the package.

As the A-lister put it, “I spent many nights at the Four Seasons because I like nice hotels. Because of that, my assistant stayed in rooms that cost $1,000 a night.”

Although Iwamasa's situation – he had to procure and administer medication for his boss – was extreme, the star experiences how an assistant gets caught up in the vortex. “You get sucked into his life and don't know how to get out of it.”

So much so that the job can take over the assistant's life. Bonnie Low-Kramen was an assistant to actress Olympia Dukakis before Dukakis passed away in 2021. Now she trains others to work in the field and has written a book about it.

She told the Post: “Sometimes I felt like I was spending more time with the Olympics than with my family.”

Bonnie Low-Kramen admits that she sometimes spent more time with Olympia Dukakis than with her own family.
A former assistant claims she was “forced” to sleep in Lady Gaga’s bed. Getty Images for The Recording Academy

It's not like a celebrity assistant's day off is the same as a regular employee's. “You're expected to drop everything and take care of problems,” Futerman said.

“On New Year's Eve afternoon, I got a call about a burst pipe. I had to take myself off work to find someone to turn off the water until we got a proper plumber. It was up to me to take care of it. It was no longer the celebrity's problem. That definitely put a damper on my New Year's Eve plans.”

Lawsuits filed by assistants against their famous bosses show the dark and strange side of life. A former friend who became Lady Gaga's assistant recalled in court documents that the $75,000-a-year job “required” her to sleep in Gaga's bed “because [Gaga] did not sleep alone.” This lawsuit was settled out of court.

Lauren Pisciotta sued Kanye West for sexual harassment and wrongful termination – which he denies. The case has yet to go to court.

Amanda Brack, a former assistant to Naomi Campbell, claimed through her lawyer that the supermodel punched her in the face and shredded her passport after a photo shoot in Morocco. She denied this and the lawsuit was also settled out of court.

Chiu described the job as that of a “frightened butler,” adding, “A celebrity's assistant can be expected to do whatever is asked of them, regardless of ethical or legal issues.” She described the relationship as a “toxic dynamic.”

Kanye West is accused GC Images
Heather H. Howard has done everything from arranging rendezvous for her celebrity bosses to protecting them from the IRS.

Heather H. Howard, author of “Chore Whore: Adventures of a Celebrity Personal Assistant,” struggled with such tasks when she was hired by a star of the TV series “Fame,” she told The Post.

“He said, 'I'm being audited by the IRS and I told them I have all the receipts and everything.' Then he said he needed me to arrange his life for this time [in terms of expense receipts for the IRS auditor to see].

“I wrote a wonderful book for him.”

She arranged “rendezvous” for a “very big producer” while his better half “was in Nepal or somewhere.”

On behalf of another client who had not had sex in a long time, “she recruited a friend who was more than thrilled to have the company of a celebrity for a night… But he didn't want me to leave the house. He wanted me to stay in another bedroom the whole time.”

Low-Kramen (who had a long and pleasant working relationship with Dukakis) says, “We all come to a line that we don't cross. Are you being asked to cover up an affair? Are you being asked to falsify documents?”

One of the perks of working for Matthew Perry was that I was able to stay in his luxury home with a pool and hot tub in the back. TheImageDirect.com

Referring to an assistant in her early 20s who had to endure a celebrity opening the door naked and not even bothering to get dressed, she added: “I think assistants can set the tone right from the interview stage. It's about discretion and mutual respect.”

However, the A-list celebrity pointed out that such a chaste attitude could lead to the work failing before it even begins:

“During the interview, a celebrity might ask his potential assistant what he is willing to do. He might ask if you are willing to cover birth control for his wife.”

Howard even remembers being sent to get an anal wart medication that his boss had prescribed in his name because he was too embarrassed to get caught.

“Will you switch places with him if the police stop him for drunk driving? It's a loyalty test to see how far you'll go.”

The A-lister then added that it can easily go too far: “Being an assistant in Hollywood comes with a lot of liability. You can end up in jail if you give your boss the wrong medication.”