Remember When These Celebrities Worked for Other Stars?

Kim’s three-episode The Simple Life arc made it appear as if she was playing assistant to her suddenly mega-famous childhood pal, but in reality she was already on that hustle. Her first stab at living that entrepreneurial life saw Kim running a closet organizing business that counted Paris, Serena Williams and Cindy Crawford as clients. 

“I would work with Paris, and I would love to organize and clean out their closets and get rid of all their stuff and sell it on eBay and then shop for them, shop for her,” she explained on Watch What Happens Live with Andy Cohen of the gig that was dreamt up one night when she was at godparents Bernadette and Sugar Ray Leonard‘s home. “That was my job. I loved it.”

Reality legends and fashion and beauty moguls gotta start somewhere, you know? 

As do future movie stars, Grammy darlings, award-winning designers and even duchesses. Because while we were all answering phones and toiling away at other entry-level positions, these celebrities-in-the-making were getting their foot in the door by doing the bidding of some pretty famous faces.

Nice work if you can get it. So, like, how do you get it exactly…?

Turns out Kim wasn’t the only Kardashian taking on The Simple Life. “I was Nicole Richie‘s assistant,” Khloe told pal Simon Huck during an appearance on his Emergency Contact podcast in October, recalling how they first became acquainted when she was working for Nicole and he was assisting then-publicist and family friend Jonathan Cheban. “I went to school with her,” the Good American co-founder continued. “She was one of my best friends growing up and so we were really, really close. And then, when she started doing Simple Life—I think it was after Simple Life towards the end—she just needed some help and I just needed a job.”

Hey nerds! Who’s got two thumbs and once served as Tina Fey‘s assistant? That’d be the actress who presumably benefited from dad Brian Williams‘ long friendship with his fellow NBC cohort, scoring a gig with the 30 Rock creator while she was on break for her studies at Yale.

“I was a production assistant on Robert Altman‘s last movie, A Prairie Home Companion; I was Tina Fey’s second assistant the summer she was shooting both Baby Mama and 30 Rock; I was the utility stand-in on the pilot of Boardwalk Empire, directed by a young, up-and-coming Martin Scorsese,” Allison shared on the Happy Sad Confused podcast of her good fortune to have entirely positive industry experiences. “Then I was on Girls.”

The actress’ career ascent turned out to be bad news for Connie Britton, who’d been hoping Katie could handle a job caring for her then-infant son Eyob in 2011. “I wanted her to be my nanny so badly and my assistant,” Connie told Page Six of Katie’s stint as babysitter. “She’s just such a phenomenal human and I remember having those conversations. She was helping me with my son, who was then just a baby, and then she said, ‘I got cast in this show called Scandal.'”

Before claiming their hip-hop throne, Jay-Z and Kanye shared an employer-employee relationship, the “Hard Knock Life” artist hiring the Chicago product to create tracks for his Roc-A-Fella Records label. Six years after working on Jay’s 2001 album Blueprint, Kanye detailed the experience in his Graduation single “Big Brother,” writing, “He got me out my momma crib / Then he help me get my momma a crib.”

Then Kanye paid it forward, agreeing to meet with a University of Pennsylvania grad who was navigating the New York music industry. “My roommate was like, ‘You gotta meet my cousin, Kanye. He’s working on Jay-Z’s album,” John recalled during a 2018 the Tribeca Film Festival event of that initial encounter. “He’s working with all these guys from Roc-A-Fella.” 

Soon the two up-and-comers were meeting at Kanye’s Newark apartment. “He would give me beats for my demo and I would write to them, and then I would sing hooks on his,” said John. And when The College Dropout artist finally scored a recording deal with Roc-A-Fella, he got his new pal the green light, too. Shared Legend, “I think they gave him the deal more so he could just make beats for them and they just wanted to keep him in house. But, eventually, he convinced everybody, ‘I’m an artist. I’m not just a producer. I’m an artist. Oh, and, by the way, I signed this really cool kid, John Legend from Ohio, and you should sign him, too.'”

A combined 32 Grammys later, safe to say that was a good call. 

Gotta admire the hustle: After filming guest parts in a 1996 episode of Spin City (“I had maybe 10 lines,” Jennifer recalled to Stephen Colbert during a 2017 appearance on The Late Show, “and you had two”) the future stars commiserated at the end-of-week wrap party. “You said, ‘Well, I’m out of a job,'” the comic remembered. “And I said, ‘I’m out of a job, too. And I said, ‘And I have a baby.'” 

A quick-thinking Jennifer offered her services and soon she was babysitting his daughter Madeline. The steady gig came to an end, however, when the actress hired a new agent that recommended she move out to L.A. “And we said, ‘Oh, that poor thing,'” Stephen recalled of the West Virginia native. “Because you were so nice….We thought, ‘Los Angeles will devour her.'” Butt-kicking Sydney Bristow? Blasphemy!

Quite the long game. Years before scoring a recurring part on Bill Hader‘s dark comedy Barry, D’Arcy actually accepted another gig from the Saturday Night Live alum. “I was his nanny for their oldest two daughters—that was my full-time job,” The Good Place alum shared on a 2018 episode of Late Night With Seth Meyers. “I was with them every day, and I still am very close with them.”

The future duchess couldn’t have scripted a better start to her Hollywood journey. As she was going on the auditions that would land her a gig on Deal or No Deal and, eventually, Suits, the L.A. native who’s said, “I think handwritten notes are a lost art form,” taught calligraphy classes at a Beverly Hills Paper Source. 

But her most high-profile work was as a freelancer, handling the save-the-dates and wedding invites for Robin Thicke‘s 2005 union to Paula Patton. The actress later gushed to Town & Country, “I just thought Meghan did a beautiful job.”

Bethenny’s Housewives roots are deep, the then-aspiring actress scoring an early gig as Kathy Hilton‘s nanny thanks to a friendship with her sister Kyle Richards. Taking care of both Paris Hilton and little sister Nicky Hilton Rothschild, “Part of the job became coming, in my Ford Probe, to get you and Nicky from Lycée, this sort of fancy French school,” Bethenny told Paris during an October episode of her Just B with Bethenny Frankel podcast. “And I remember, we’d go with Kyle to the Mobile Mart or the gas station after. And I would take you guys ice skating.”

She wouldn’t go as far to claim she was the one that helped Justin Timberlake bring his sexy back following his legendarily messy 2002 split with Britney Spears, but the future Step Up standout was dancing backup for the pop star “like, during-after the breakup,” she shared on Watch What Happens Live with Andy Cohen. And while she was clear that she was absolutely “not the rebound,” they did have a brief something. 

“We dated,” she told a stunned Andy Cohen on the 2017 episode. “Not that long. We were, like, friends, friends that then dated and then we’re just really good friends now.” Really, despite that time period being what she called the “craziest, wildest thing,” she insisted, “It’s not as salacious as everyone thinks.”

Think the Full House alum relied on her considerable connections to score a coveted one-to-two-day-a-week gig with Zac Posen while studying at New York University? How rude! Rather, to get the designer to say, “You got it, dude,” the future two-time CFDA Womenswear Designer of the Year “came in person and knocked on the door to get her internship,” he recalled to People in 2007, “which is four steps farther than most interns go. She had that drive and that’s what makes someone special.” Duly impressed by the future cofounder of lines The Row and Elizabeth and James, he told The Daily, “I hired her on the spot. She was great.” 

“It was so glamorous,” the future Mindy Project lead recalled to Conan O’Brien of her time spent working as a 19-year-old intern on Late Night with Conan O’Brien. While she dutifully took the train down from Dartmouth in New Hampshire, she wouldn’t exactly call herself a model employee. “I was also the worst intern that’s ever worked on the program,” she said. “I wanted to work there not to learn how to photocopy things, but to watch you….I wouldn’t do the things I was hired to do. I would just kind of follow you around.”

Entirely starstruck by her “comedy hero,” she dreamed of one day being a guest in front of the camera, but, “It seemed too crazy to think about.”

Who knew the Modern Family standout had friends in low places? Well before Eric was collecting Emmys and making us all love clowns, the Kansas State University sociology major spent one night in 1995 working security for a Garth Brooks concert near campus. “Last night I finally got to say you’re welcome for keeping him safe that night,” Eric joked of meeting up with his former boss at a 2017 show, “and basically giving him the wonderful career he’s had thus far.”

Try to keep up: “People will say ‘assistant.’ They always have it wrong,” Kim told Andy Cohen of her early days as Paris’ sidekick. Rather than fetching dry cleaning, booking travel and performing other menial tasks, Kim’s responsibilities included getting rid of the heiress’ impulse buys and color-coordinating her sizable wardrobe. Getting paid for sorting through designer wares? That’s hot.