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14 Celebrities Who Make the Best or Most Horrendous Bosses

Kenny Chesney Kept Over 100 People Employed During the Pandemic

When his tour was postponed during the chaotic early months of the pandemic, he paid his crew out of his own pocket: “I had to make a decision if I was gonna keep my lifestyle the way it was, or if I’m gonna take care of my people.”

Taryn Manning Needs Her Employees Squeaky Clean

The Orange Is the New Black star (allegedly) headbutted her assistant, whipped her with a wet towel and drenched her face with Windex. And that was the second (alleged) assault on the same assistant.

Jennifer Hudson Is Outrageously Generous

Hudson bought her assistant, Walter Williams, an entire house for Christmas in 2013. All he had to do in return was have his reaction posted to her Instagram (and also serve her every whim at all hours of the day).

Jennifer Lopez Made the Quarterly Check-In Quite Awkward

She fired her makeup artist, Scott Barnes, for leaking unflattering details about her life to the press. Except he was able to prove that he wasn’t the leaker, and she was forced to hire him back: “I went right back to work with her, and we just never spoke about it again, which is even weirder.”

Emma Watson Is Extremely Passive Aggressive

One employee said that she “takes perfectionism to the extreme,” meaning that if you screwed up, “she’d give you the silent treatment! It was so awkward.”

Sandra Bullock Is a Huge Proponent of Little Treat Culture

She reportedly gives out gifts like spa treatments for employees’ birthdays, and one year shelled out $10,000 year-end bonuses for pretty much no reason.

Ellen DeGeneres Has a Zero-Tolerance Policy

She reportedly leaves feedback for her household employees in the form of passive-aggressive sticky notes, berating them for poor light-switch etiquette or misplacement of a salt shaker.

Courtney Love Tried to Turn Her Personal Assistant Into a Criminal Mastermind

Her assistant accused her of acting “with an improper and evil motive amounting to malice or despicable conduct” when she made her send fake legal orders and try to source a computer hacker.

Rihanna’s Forced Happy Hours

She describes compulsory partying among her reports: “After work, when I’m literally in my kitchen having a drink, I invite all my staff. And we work.” She did serve as her assistant’s bridesmaid, which was pretty cool of her.

Naomi Campbell Won’t Stop Throwing Phones at People

She’s been accused of physically assaulting employees at least 10 times, but she has a special place in her heart for phones as projectiles. She pled guilty to assaulting a personal assistant with a cell phone in 2000, and threw a Blackberry at her housekeeper in 2007. When she was assigned a PR person to improve her public image after that, she (allegedly) assaulted them as well.

Mariah Carey Fired Her Nanny for Being a Good Nanny

Carey’s nanny filed a lawsuit claiming that she “terminated Plaintiff after berating her for exhibiting too much affection towards her children.” They eventually settled out of court.

Oprah Winfrey Went on Strike to Get Her Producers a Raise

She went on strike in the ‘80s in support of her producers, and when her bosses refused, she gave them sizable bonuses out of her own pocket.

Christian Bale’s Assistant Had to Sniff His Pits

Bales personal assistant claims it took five years of intensive therapy to recover from the PTSD his job gave him: “I would do anything from sniffing Christian’s armpits for B.O. right before he hit the red carpet to making emergency sock runs if Christian was all out of clean ones.”

Dolly Parton Pays for Her Employees’ Education

She covers 100 percent of tuition, books and other fees for Dollywood employees seeking a degree.


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