Jennifer Aniston’s $300M Empire Began With a Job She Says She Totally Flopped At

Jennifer Aniston is now one of Hollywood’s most recognizable and acclaimed actresses, best known for her roles in “Friends,” “The Morning Show,” “Horrible Bosses,” and “The Break-Up.” With an Emmy Award, a Golden Globe and several Screen Actors Guild Awards to her name, Aniston has built a celebrated career over the past three decades. But before she became a household name, her path to stardom was far from glamorous.

Jennifer Aniston at the 76th Primetime Emmy Awards held at Peacock Theater on September 15, 2024 in Los Angeles, California. (Photo by Michael Buckner/Variety via Getty Images)

In a 2019 interview with InStyle, Aniston reflected on the early days of her career, revealing the string of odd jobs she worked while trying to break into the entertainment industry. Among them: telemarketing.

The Job That Wasn’t

“I had moved away from home. I had been on six failed television shows,” Aniston said. “I waitressed for years in New York before I got anything. And I was a telemarketer selling time-shares in the Poconos. I didn’t make one sale. I was terrible at it. I was like, ‘Why do we have to call people at dinnertime?’”

Long before her breakout role as Rachel Green on NBC’s “Friends,” Aniston also earned extra cash by giving haircuts.

“I cut hair for 10 bucks a head in junior high,” she recalled. “I cut my dad’s hair, and he was on a soap opera. But then he admitted to me 15 years ago that he would go in and have the hairdresser on set clean it up.”

Aniston’s persistence eventually paid off. In 2019, she took on a dramatically different role as co-lead and executive producer of “The Morning Show,” Apple TV+’s high-profile drama series alongside Reese Witherspoon and Steve Carell.

In the series, Aniston plays Alex Levy, a veteran anchor navigating the fallout after her on-air partner, Mitch Kessler (Carell), is fired for sexual misconduct. Witherspoon plays Bradley Jackson, a reporter thrust into the spotlight as Mitch’s replacement.

“The show gives you a behind-the-curtain peek at a lot of things — what it takes to pull off a morning show, the unique lifestyle of these anchors, the obsession with celebrity culture, and humanity in the midst of corruption,” Aniston told InStyle. “Plus we’re addressing the ugly truths of how men have treated women in our society, particularly in the workplace, for all these years.”

Although “The Morning Show” premiered after the rise of the #MeToo movement, Aniston and Witherspoon had pitched the concept earlier.

“The show was always about the abuse of power, and women and sexism. We sold it in the summer, and then Harvey [Weinstein] happened in the fall,” Aniston said. “Reese and I were like… ‘The show is writing itself.’ It was as if the universe were begging for this patriarchal society to be exposed.”

Aniston emphasized that the show aims to spark conversations about systemic issues and inspire meaningful change.

“There’s a new playbook that’s being written in real time, and this show looks at how we’re finally taking steps to acknowledge and dismantle the old, dysfunctional ways of doing business so we can level the playing field,” she said.

From failed auditions and telemarketing calls to award-winning performances and executive producing, Aniston’s journey highlights both resilience and the shifting culture in Hollywood.

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