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Home Celeb Style

What It’s Really Like Working for Leonardo DiCaprio: An Insider’s Look

James Graham by James Graham
11/05/2026
in Celeb Style
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What It's Like To Work For Leonardo DiCaprio
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It’s been over two decades since Leonardo DiCaprio took to the skies in the 2003 blockbuster The Aviator, and a full ten years since he finally clutched that long-awaited Academy Award. But for actress Kasi Brown, the memories of working alongside the Hollywood heavyweight remain as fresh—and fond—as ever.

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Stepping into the coveted role of DiCaprio’s personal assistant during the filming of the Martin Scorsese epic, Kasi was given a rare, behind-the-curtain look at one of the world’s most famously private stars.

“Leo and I always had fun on set,” she recalls, painting a picture of a surprisingly relaxed working environment. “[We loved] to observe people and goof around playing characters, doing accents, whatever.”

Far from the demanding diva stereotype, Kasi fostered a playful dynamic with the A-lister. She would often poke fun at his immense fame, jokingly bowing and adopting a subservient, beaten-down voice. “‘Yes, sir, anything you like sir, anything else, sir?'” she would tease. His reaction? A genuine laugh and a swift command to knock it off.

It’s All About Connections

Landing a gig with one of the biggest actors on the planet usually involves mountains of resumes and gruelling interviews, but Kasi admits it was a natural connection that got her foot in the door.

Her friend, Kayce Brown, was already established as DiCaprio’s assistant, having worked with him during the 2002 filming of Catch Me If You Can. When Kasi flew out to simply hang out with her friend on the set of The Aviator, fate stepped in. As the production moved to Los Angeles and Kayce bowed out of the position, Kasi was the automatic choice to seamlessly take over the reins.

The Man Behind the Movie Star

Spending exhaustive hours on set allowed Kasi to see the nuances of DiCaprio’s personality that the cameras rarely capture. Among her biggest takeaways was his deep, underlying desire for a normal life.

He confessed to her that Halloween was his absolute favourite holiday. The reason? The costumes offered a rare shield of anonymity, allowing him to “walk amongst people and interact with them without recognition.”

Beyond his desire to fly under the radar, Kasi notes his sharp intellect. She describes him as incredibly smart, armed with an in-depth knowledge of “politics, pop culture, history, you name it,” perfectly balanced by a “wicked sense of humour.”

“He’s extremely down to earth, and he likes to share stories and life experiences with people,” she adds.

A Lasting Loyalty

Perhaps the most telling aspect of their time together is what happened after the director yelled “cut” for the final time. In an industry notorious for its fleeting, transactional relationships, DiCaprio’s support didn’t end when Kasi’s employment did.

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As she stepped away from assisting to chase her own Hollywood dreams as an actress, her former boss remained a steadfast supporter. Proving his loyalty, she notes that he continues to make the effort to keep in touch, offering invaluable professional feedback and encouragement as she navigates her own path in the industry.

Tags: assistantcelebritydream jobLeonardo DiCaprioOscarsworking
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James Graham

James Graham

With over 20 years as a journalist and TV producer, James Graham has a wealth of experience covering the full media spectrum. James has a formidable reputation as a talented media veteran and worked as a reporter, script writer and as the producer of the TV documentary The Road To Athens. He has worked across newspapers, radio and the biggest flagship magazine brands in Australia and New Zealand. Previously, James was the News Director at Woman's Day and New Idea. Whether filing celebrity exclusives, or some of the biggest real-life splashes of recent years, James’ career has always been at the frontline of mainstream media. When not writing, you’ll find him at Royal Randwick, his beloved Long Reef Golf Club on the Northern Beaches – or visiting his mum in his native New Zealand.

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