When a celebrity hits a certain level of fame and fortune, it becomes something of a rite of passage to hire an entourage. For some, this can mean paying the salaries of an entire team of people devoted to ensuring said celebrity never again has to do the kinds of chores most of us fit into our day-to-day — say, washing the car or taking out the trash.
“There are two types of celebrities,” TMZ‘s Harvey Levin once claimed to the Los Angeles Times, those “that want everybody around them to think it must be the president” and the ones “who just would like to blend” and “don’t make a fuss.” He noted, “The smart celebrities are the ones who realize that a true sign of stardom is somebody who doesn’t have to act like a star.” So while pretty much every star worth their salt has at least a personal assistant, stylist, and publicist on the payroll, others step it up a notch by adding life coaches, spiritual advisers, and more to their entourages. Of course, in the realm of “Hollyweird,” this can be taken to further extremes, with certain celebs hiring employees to perform oddly specific tasks that the average person would find pretty ridiculous.
We’ve dug up some examples of celebrity eccentricity and excess gone wild, so keep on scrolling to find out the weirdest things celebs have hired people to do.
Snoop Dogg has his own dedicated blunt roller
Snoop Dogg’s love of marijuana is legendary — in a 2012 Reddit AMA, he claimed to smoke “81 blunts a day.” Given that prodigious intake, it shouldn’t be surprising to learn that he has a full-time employee whose sole job is to roll those blunts. During a joint interview with Seth Rogen on The Howard Stern Show in October 2019, the rapper clarified that he pays the guy an annual salary of between $40,000 and $50,000 to ensure he never goes without having a freshly-rolled blunt at his disposal. “That’s his J-O-B, his occupation,” Snoop explained to the shock jock. “On his resume, it says, ‘What do you do? I’m a blunt roller.’ P-B-R, professional blunt roller.”
Rogen confirmed that he’d seen Snoop’s staffer in action. “He knows how to gauge the look on someone’s face when it seems like they want a blunt, and if they do, he gives you one,” Rogen said. “Timing. That motherf**ker’s timing is impeccable,” Snoop agreed, even comparing his blunt-roller to Lurch from The Addams Family with, “You rang?”
Rogen admitted he was contemplating hiring his own dedicated roller. “Honestly, the amount of time I spend rolling joints, it might be worth my while financially to hire someone to do that,” he pondered with a laugh.
CeeLo Green reportedly paid a gum handler and sweat wiper before a gig
CeeLo Green is perhaps best known for singing the Gnarls Barkley hit, “Crazy,” churning out the equally infectious song “Forget You,” and serving as a coach in the early seasons of the NBC singing competition, The Voice. But when it comes to what he expects from his employees, the demands are apparently a bit on the unusual side. According to a 2010 gossip item in Page Six, Green attended a release party for his album, Lady Killer, where he also performed. “He had someone wipe the sweat from his brow, as well as put a piece of gum in his mouth, before the show,” a so-called “spy” claimed to the outlet.
Having an employee reportedly place chewing gum in Green’s mouth for the musician may seem weird, but it’s certainly not the shadiest thing about the singer. That said, it does seem to fall in line with Green’s eccentric persona. “I’ve been such an oddball my whole life,” he admitted around that time in an interview with The Guardian. “I like to dress to match my luggage. If my luggage is black, I’ll dress in black, if it’s red, I’ll dress in red. It makes things easier to figure out.”
Lady Gaga supposedly required a bedtime cuddler
Lady Gaga’s personal assistant had some fairly specific job requirements, one of which seemed to be crossing a line. That came to light in 2013, when Jennifer O’Neill, who worked as Gaga’s personal assistant, sued the singer for nearly $400,000 in unpaid overtime wages.
Among the details contained in O’Neill’s deposition, reported the New York Post, was that Gaga allegedly insisted O’Neill sleep with her. “I was by her side virtually 24 hours a day, seven days a week,” O’Neill testified. “That includes sleeping in the same bed with her. Because she did not sleep alone.” Asked if she thought that snuggling up in bed with her boss was a “required” aspect of her job, O’Neill replied, “I felt it was.” When accompanying the Mother Monster on tour, O’Neill claimed, “I did not have my own hotel room … I had no privacy, no chance to talk to any family, no chance to talk to any friends, no chance to have sex if I wanted to have sex.”
Gaga fired back in her deposition, reported The Hollywood Reporter, calling O’Neill a “f**king hood rat who is suing me for money that she didn’t earn.” The case was eventually settled for an undisclosed amount.
Billionaire Larry Ellison hired a yacht basketball retriever
Larry Ellison is one of the richest people on the planet, with Forbes estimating the Oracle co-founder’s net worth to be a staggering $75 billion. Back in 2014, reported The Wall Street Journal, Ellison was part of a consortium (along with media moguls Oprah Winfrey and David Geffen) attempting to purchase the Los Angeles Clippers, after the team’s previous owner, Donald Sterling’s, racist comments had him banned for life from the NBA.
Owning an NBA team, the article suggested, would be right in line for such an extreme basketball fan as Ellison. In fact, that WSJ article also contained an odd factoid about Ellison and his love of basketball. According to Tom Ehman, who took care of all matters for Ellison relating the yacht race, America’s Cup, he “has had basketball courts on at least two of his yachts.” In the words of the outlet, Ehman elaborated by claiming that the hoops-loving billionaire “liked to relax by shooting hoops on these courts, and has had someone in a powerboat following the yacht to retrieve balls that go overboard.”
P. Diddy once had his very own umbrella holder
It’s one thing to hold an umbrella atop the head of one’s boss, but it takes a very special type of person to turn that into a full-fledged career. That’s the case with Fonzsworth Bentley, the one-time personal valet to Sean Combs, a.k.a. Puff Daddy, a.k.a. P. Diddy.
According to a 2004 profile in The New York Times, a photo of Bentley using an umbrella to keep Diddy shaded from sunshine as he walked on a St. Tropez beach became a sensation. “That picture was the biggest marketing campaign that any unknown has ever launched,” said Bentley. “Jay Leno talked about that picture, so did Regis and Kelly. It was in Time, Newsweek, People. It made me famous overnight.”
In fact, Diddy’s umbrella-holder parlayed his instant fame into his own music career, while insisting he was never a “butler,” but rather a personal assistant. Bentley’s duties, the outlet noted, “included waking his boss in the morning, fetching caramel macchiatos from Starbucks, fielding phone calls, packing and unpacking P. Diddy’s suitcases, and picking out his clothes.”
NBA star Nick Young has a security team to guard his shoes
It’s not unusual for celebrities to have security personnel on their payrolls in order to stay safe and secure. Former NBA Star Nick Young, however, has taken the notion of personal security to a whole new level by extending that protection to his footwear.
A 2015 Sports Illustrated profile of the Los Angeles Lakers star, who goes by the nickname “Swaggy P,” included some unique information pertaining to his 6,600-square-foot mansion in Tarzana, Calif. One of the nuggets of intel divulged was that Young was in the midst of converting a standalone building on the property into a “shoe house” to store his vast collection of sneakers at the time.
“He employs not one but two ‘shoe keepers,’ who oversee his 500-plus pairs of sneakers, a collection that includes Vans fitted with roller-skating wheels,” noted SI. Describing his sneaker storage facility in an interview with Mr Porter the following year, Young said, “It’s like a little treehouse for my sneakers.”
Mariah Carey's team apparently ensures she never has to do anything for herself
Unlike some performers who have been described as “divas,” Mariah Carey wears the label with pride. British TV presenter Kate Garroway offered some insights into how much that carried into Carey’s personal life by detailing what happened when the singer appeared on her U.K. morning show, GMTV.
“I’ve heard a lot of rumors about her being a diva over the years and guess what? It turns out it’s all true!” Garroway told the Daily Mail, claiming that “the amount of people she had in her entourage was hilarious.” This crew, she alleged, included “two people to lower her on to the GMTV sofa, in case her dress got crushed, one person to walk in front of her backwards at all times in case she fell over and several people behind the camera making sure she was going to be filmed from the right angle!”
Meanwhile, the singer’s vocal coach, Carrie Grant, revealed in an interview with Virgin radio (via the Mirror) that Carey reportedly employed “a woman that held her drink with a straw. That’s all she does, flies around the world as a drinks holder.”
Prince Charles reportedly has a personal undresser
The perks of being a member of Britain’s royal family are somewhat obvious, yet there are some that are even stranger than anyone realized. This came to light with the publication of Brian Hoey’s 2011 book, Not in Front of the Corgis!, which documents some of the weirder and wackier royal traditions.
One of these, according to some excerpts in the Daily Mail, is that Prince Charles has reportedly never undressed himself or even picked up after himself. The Prince of Wales apparently has a team of valets to take care of all that for him; in fact, one valet’s duties allegedly “include[s] ironing the prince’s shoelaces whenever his shoes are taken off.”
Being a royal valet is not all glamor. Another excerpt from the book alleges that Prince Charles’ mentor, the late Earl Mountbatten, had apparently gained a few pounds when he discovered he was unable to fit into his Life Guard breeches to attend the Queen’s birthday parade. To squeeze him in, Mountbatten’s valet sprinkled talcum powder inside the pants — which, noted the Daily Mail, were so tight “the earl could not sit down or go to the toilet and when the event was over valet William Evans had to peel the breeches off his master’s sweaty legs.”
Justin Bieber's entourage wouldn't be complete without someone to hold his food for him
Justin Bieber made a big impression when he appeared on Saturday Night Live, hosting in 2013 after making his SNL debut as a musical guest in 2010. During an interview with Howard Stern, former SNL cast member Bill Hader recalled one of Bieber’s appearances.
“Justin Bieber showed up with like 20 guys,” Hader told Stern, explaining the difficulties this presented backstage, which he described as “a very small, constricted place.” Bieber, Hader added, “had a guy holding a slice of pizza. A guy holding a Diet Coke. Going around stage, you’re trying to fight through all these people to get dressed.”
Hader had more to say to authors James Andrew Miller and Tom Shales in Live From New York: An Uncensored History of Saturday Night Live. “I really didn’t enjoy having Justin Bieber around,” he admitted. “I didn’t hate the guy, I just wasn’t into it. I’m pitching jokes to this kid?” Noting that the Biebs was “the only one who lived up to the reputation,” Hader continued, “I think that’s the only time I felt that way in my eight years there.”
Oprah Winfrey has employed her own personal 'bra whisperer'
With Forbes estimating Oprah Winfrey’s net worth to be a whopping $2.6 billion, it’s understandable that she would spare no expense when it comes to finding brassieres that fit her perfectly. To that end, Winfrey famously enlisted the services of “bra whisperer” Susan Nethero. So enamored was Winfrey of Nethero’s skills, she invited her on her talk show five times, recalled Simply Buckhead.
In 2014, Nethero shared some of her bra knowledge with USA Today, including her discovery that “most women wear only half the bras they own because they don’t fit, don’t like the style, or they’re plain uncomfortable.” According to Nethero, a woman should own between five and seven “good working bras that they really enjoy wearing.” She also detailed how women can get more wear out of a bra. “You can double the life of a bra with proper wear and care,” she added, advising women to wear a bra twice between washings and to “rotate” usage by not wearing “the same bra on consecutive days. Bras need to rest in between.”
Ludacris once hired a guy to carry extra Gameboy batteries
Ludacris was once apparently so addicted to video games that he took his portable Nintendo Gameboy with him everywhere. According to a brief snippet in Kathryn and Ross Petras’ 2009 book, Unusually Stupid Celebrities: An All-Star Compendium of Stupidity, a member of the rapper-actor’s entourage was once asked to describe what he did. “I do the batteries,” the employee reportedly replied, indicating that he was specifically in charge of ensuring there was always a supply of charged Gameboy batteries on hand for when his boss was struck with the desire to play.
It would seem, however, that the Fast & Furious star’s extreme approach to gaming eventually settled down. In a 2004 interview with IGN, Ludacris admitted, “To be real with you, I don’t even get to play video games as much as I would like to. I used to be a video game freak, but I’ve kind of like eased back.”
Pink's assistant is required to squeeze what before her concerts?
Pink is known for her enthusiastic live performances, and she once revealed a bizarre secret behind her onstage energy. As Today reported in 2004, the “Family Portrait” singer employs her own personal “nipple tweaker” to get her all revved up for the crowd. “I need my nipples squeezed before every show,” Pink said. “It gets me pumped to go on stage. My assistant Jackie has it down to a fine art.”
According to the outlet, the singer’s rep wasn’t available to either confirm or deny this backstage secret — but a source indicated it was a safe bet that the quote did indeed come from Pink. “I’m sure she did say it,” claimed the insider. “She’s a laugh riot.” Need more proof? In an interview with The Daily Star that same year, as quoted by PopDirt, Pink explained the whole thing was part of “this little ritual” that she does before each performance. “I usually drink a couple of beers and do my makeup … Oh, and I also make my best friend grab my nipples — that gets me good to go.”
No word on whether or not Pink and her assistant have since moved on to a less personal pre-show ritual.
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