Job ads for assistant positions rarely include jobs that involve injecting your boss with illegal drugs, sharing his bed or enduring the kind of physical assault that district attorneys consider to be rape.
Nor does it warn that candidates’ lives will be dedicated to being beleaguered superstars who routinely test the moral limits of those around them. But that’s the life of a celebrity assistant.
Consider the afternoon of Oct. 28, 2023, when Kenny Iwamasa, who was working as Matthew Perry’s live-in assistant, injected the Friends star with a lethal dose of ketamine.
Iwamasa recalled his boss’ last words to him as he was confronted by police after his arrest: “Shoot the big one.” He pleaded guilty to conspiracy to traffic ketamine. Perry died while floating in a hot tub in his backyard.
“My initial reaction is that it’s heartbreaking in a lot of ways,” Meryl Futerman, a former celebrity assistant and author of the novel Don’t Make a Scene: Struggles of a Celebrity PA, told The Post. “But I also know that being a personal assistant is a very gray area — in terms of what you’re asked to do, what you can’t help but do, and what’s hard to say no to.”
Speaking to the Post, a veteran Hollywood executive agreed: “You can’t say no. When Matthew Perry asks for a refill, you get it. He was helping him get what he needed to get through the day. Now the person with the least power” — someone without access to the expensive lawyers and publicists who can protect celebrities — “has been arrested and pleaded guilty.”
Of course, keeping his boss’s drug habit a secret was paramount. Iwamasa’s LinkedIn profile begins with his most notable qualities: “I am discreet, honest and maintain absolute confidentiality.”
The arrest of the 60-year-old man from Midland, Michigan, was said to have come as a “surprise” to his friends and family.
Not all of Perry’s assistants had a hard time. He had Briana Brancato, whose job, judging by her Instagram and his book, Friends, Lovers and the Big Terrible Thing, mainly consisted of lounging poolside and being Perry’s best friend.
Former celebrity assistants and entertainment industry insiders told The Washington Post that the reality of being a celebrity assistant is a mix of glamorous living, being within reach of the glamorous world of Hollywood stars, and being forced to do reprehensible things.
“It’s a dangerous road,” a top Hollywood star told The Post, “and they don’t want to lose their job if they’re asked to do something unethical, so they make their assistants feel obligated. I’ve seen celebs get their assistants to carry drugs through the airport. Some assistants will do anything.”
One top producer told The Post that saying no is generally not an option for those who want to continue working for privileged superstars. If they’re demanding, “it’s very difficult, and sometimes[celebrities]get violent. You either put up with it or find another job,” he said.
Stars can take solace in the fact that they don’t need an assistant. “It’s not hard,” the producer continued. “People want these jobs.”
More importantly, they’re looking for the next 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 “at a moment’s notice” and that it would be impossible for her to get another job in the film industry. “The blacklisting was permanent.”
But the assistant’s salary might help make things tolerable: Producers estimate that a full-time assistant could make $150,000 a year, and whether or not they live with their boss, ample perks come with the package, including meals at fine restaurants, car rides, and trips on private jets.
The A-list star said: “I like luxury hotels, so I stayed at the Four Seasons a lot, so my assistant was staying in a $1,000-a-night room.”
Iwamasa’s situation is extreme – having to source and administer drugs for his boss – but the A-list actor sees first-hand the way his assistants get caught up in it: “I get so caught up in his life, I don’t know how to get out.”
The job can even determine the assistant’s life: Bonnie Law-Claymen was assistant to actress Olympia Dukakis until her death in 2021, and now coaches others in the field and has even written a book about it.
“At times it felt like I was spending more time with Olympia than I was with my family,” she told the Post.
A celebrity assistant’s days off aren’t the same as a regular employee’s: “They’re expected to drop everything and address the issue,” Futerman said.
“On the afternoon of New Year’s Eve, I got a call that a water pipe had burst. I was forced to stop what I was doing to find someone to turn the water off until a proper plumber could arrive. It was up to me to deal with it. It wasn’t a celebrity issue anymore. This completely ruined my New Year’s Eve plans.”
A lawsuit filed by an assistant against her famous boss reveals the dark and strange side of assistant life. A former friend who now works as an assistant to Lady Gaga recalled in court documents that her $75,000-a-year job “required” her to sleep in Gaga’s bed because “Gaga wouldn’t sleep alone.” The suit was settled out of court.
Lauren Pisciotta has sued Kanye West for sexual harassment and wrongful termination, which West denies. The case has yet to go to court.
Naomi Campbell’s former assistant, Amanda Black, claimed through her lawyer that the supermodel slapped her in the face and shredded her passport after a photo shoot in Morocco, charges she denies and the suit was settled out of court.
Chiu described the job as being like a “frightened butler,” adding that “celebrity assistants are made to do whatever they’re asked to do, regardless of whether it’s ethical or legal.” She described the relationship as a “toxic dynamic.”
Heather H. Howard, author of “The Errand Girl: The Adventures of a Celebrity Personal Assistant,” struggled with such a job, she told The Washington Post when she was hired by the star of the TV series “Fame.”
“He said, ‘I told them I’m being audited by the IRS and I have all my receipts and everything,’ and he wanted me to make his living in the meantime (in terms of expense receipts for the IRS auditors to see).”
“I created a great book for him.”
She set up a secret rendezvous for a “big producer” while his partner was “in Nepal or somewhere.”
On behalf of another client who hadn’t had sex in a long time, she “hired a friend who was more than happy to have a celebrity with me for a night… but he didn’t want me to leave the house. He wanted to stay in a separate bedroom the whole time.”
According to Law-Clamen (who had a long and successful working relationship with Dukakis), “There are lines that nobody should cross. Are you being asked to cover up an affair? Are you being asked to forge documents?”
Referring to a female assistant in her early 20s who had to endure celebrities opening doors naked and not making an effort to get changed, she added: “I think assistants can set the tone from the interview stage onwards. Talk about discretion and mutual respect.”
But the A-lister pointed out that such chaste behavior could derail the job before it even begins.
“During the interview, the celebrity might ask the potential assistant what they would do for him. They might ask if he would pick up his wife’s birth control pills.”
In fact, Howard remembers being dispatched to get a prescription for her boss’s anal wart treatment written in her name because she was embarrassed to be seen doing it herself.
“If the police pulled him over for DUI, would you trade seats with him? It’s a test of your loyalty.”
And the A-list actor added that it could easily go too far: “Being an assistant in Hollywood comes with a lot of responsibility. If you give your boss the wrong pills, you could go to jail.”
