Sneak peek: Oxygen’s “Like A Boss”

The boss-assistant relationship gets the reality ensemble treatment in Oxygen's Like A Boss (pictured), a new series from Real Housewives of Beverly Hills producer Evolution Media and executive producer Nick Cannon.
March 29, 2016

The idea for a reality show about bosses and their assistants has been shopped around to networks for years, but Oxygen believes it has tapped into the right formula with the Nick Cannon-fronted Like a Boss (pictured).

Due to premiere on the NBCUniversal-owned cable net tonight (March 29) at 9 p.m. EST, the show follows four Atlanta-based millennial-age assistants as they slug it out doing tasks such as cleaning bathrooms, buying cosmetics, doing Google research and other thankless tasks for bosses with established careers in media and real estate.

Cannon, who has hosted America’s Got Talent and recently starred in Spike Lee’s Chi-Raq, originated the idea through his production shingle Ncredible and took it to Oxygen, which in turn brought in The Real Housewives of Beverly Hills and Botched producer Evolution Media to develop it further.

With a well-known (and well-connected) talent on board to star and exec produce, Evolution saw a project with franchise potential, and with appeal to both young viewers entering the workforce and their older counterparts who are now bosses.

Evolution has worked on 12 other projects with NBCUniversal-owned nets, but this is the company’s first production for female-skewing Oxygen.

“We can all identify with what it’s like to be in your 20s: [you] think you know everything and think you should be doing your boss’ job,” says Alex Baskin, Evolution’s executive VP of programming and development (pictured below, right). “But you’re consigned to the menial tasks that one needs to do to earn your education from the school of hard knocks.”

The cast includes two go-getting assistants with families and career ambitions, and two aimless assistants just entering the workforce and seemingly unaware of the pecking order.

douglas ross, alex baskin

Evolution Media’s Douglas Ross, Alex Baskin

There is Amber Grimes, a former assistant-turned-entertainment manager who grapples with returning to the assistant life for the opportunity to work for Cannon; the perennially broke Devin Simpson, who lives at home with mom while assisting real estate agent Blair Myers; Rian Parish, a busy mom who hopes to break into the media business through assistant radio host Big Tigger; and the temperamental Drekia Glenn, assistant to music exec Abou “Bu” Thiam.

“Whenever we cast an ensemble show, it’s important to try to represent a variety of personalities,” explains Evolution CEO Douglas Ross (pictured, left).

“We also found that because the assistants are part of the millennial generation, this was a pretty good representation of the different kinds of millennials out there,” he continued. “There is a big thrust in [this] generation of people who are a little aimless and maybe a bit spoiled and those who have big dreams.”

The big challenge in casting for Evolution was finding assistants unafraid to open up on camera.

“It’s always difficult to capture the upstairs-downstairs dynamic because employees know that their employers are going to see exactly what they’ve said or corners that they’ve tried to cut,” says Baskin. “Families are stuck with each other, but it’s different when you’re in a professional relationship that might change as a result of being on a television show.”

Meanwhile, casting the bosses was slightly tricky in that Evolution had to persuade employers accustomed to being the center of attention to cede the spotlight to their underlings.

That’s where Cannon came in handy: he would talk to any reluctant bosses, tell them he was on board with the concept and they would fall in line.

“Before we started taping, the bosses started to realize, ‘Oh wait a minute, I’m not the star in this duo story,’” says Ross. “Once they got used to the idea they all played along and didn’t give us any grief.”

If viewers buy in, Evolution, NCredible and Oxygen are hoping for a Housewives­­­-style franchise. New boss-assistants could be added in future seasons and the concept is catered to spin-offs set in other U.S. media markets, such as New York, Los Angeles or Chicago.

“We certainly have enjoyed that on the Real Housewives shows that we do, and we don’t see this as any different,” says Ross.

  • Check out an exclusive clip from Like a Boss below. Please note that the content is currently only available to U.S. viewers.

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