Inside Meghan's struggle to crack Hollywood and the one project that actually worked for her: How the Duchess went from 'briefcase girl' on Deal or No Deal and failed TV pilots to her big break on Suits... years before her luxury life
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Long before she was enjoying a life of luxury in Montecito, Meghan Markle was a young actress in Hollywood with dreams of achieving success.

At that time, the Duchess of Sussex led a notably simple life, juggling several jobs in Tinseltown while awaiting her breakthrough.

Even though their $100m Netflix deal is reportedly ‘dead’, the couple has launched a business empire since ‘Megxit’, despite Meghan’s rocky start in acting.

In his biography of the Duchess of Sussex titled *Meghan Misunderstood*, royal author Sean Smith unveiled how Meghan managed to make ends meet in Hollywood.

This included her role as a restaurant hostess, though her most intriguing job was as a calligrapher, specializing in elegantly stylizing words.

‘Meghan had exquisite handwriting, so it seemed a perfect “resting” job and was apparently “super lucrative”,’ Smith wrote. 

During this period, Meghan also worked as a correspondent for Dolce and Gabbana and crafted the souvenir place cards and envelopes for Robin Thicke and Paula Patton’s wedding in June 2005.

Meghan even taught ‘informal classes’ in calligraphy from a stationary store in Beverly Hills.

Meghan Markle as a 'briefcase girl' on the US version of Deal or No Deal

Meghan Markle as a ‘briefcase girl’ on the US version of Deal or No Deal 

Meghan as Rachel Zane alongside her Suits co-star Patrick J Adams

Meghan as Rachel Zane alongside her Suits co-star Patrick J Adams

Meghan in 2010. Her acting career got off to a rocky start in the 2000s

Meghan in 2010. Her acting career got off to a rocky start in the 2000s 

But while her calligraphy work was taking off, Meghan struggled to get her acting career off the ground. 

According to Smith Meghan was ‘trapped on the annual pilot-season lottery’ and she would go ‘five straight years making pilots that never amounted to much’. 

Her first professional film role where she played the part of Natalie Hot Chick in Ashton Kutcher’s romantic comedy A Lot Like Love was released in 2005.

This marked a trend for Meghan where she would either be cast in very minor film roles or failed TV pilots.

These gigs included appearances in popular films from the 2000s and early 2010s including Get Him to Greek, Remember Me and Horrible Bosses.

Her most successful role at this time was as a ‘briefcase girl’ in 34 episodes of the American version of Deal or No Deal. 

Finally her big break came in 2011 when she was cast as Rachel Zane in the legal drama Suits which she starred in for seven seasons.

It has been estimated that Meghan took home $50,000 per episode resulting in a salary of $450,000 a year.

Meghan on Deal or No Deal. She appeared in in 34 episodes of the show

Meghan on Deal or No Deal. She appeared in in 34 episodes of the show 

Meghan's black and white headshot from her early acting days

Meghan’s black and white headshot from her early acting days

Meghan as Rachel Zane in Suits. After years of unsuccessful auditions the Legal Drama proved to Meghan's big break in 2011

Meghan as Rachel Zane in Suits. After years of unsuccessful auditions the Legal Drama proved to Meghan’s big break in 2011

She would leave the show in 2017 when she took a dramatically different career path by marrying into the Royal Family. 

However Meghan’s stint as a working royal was short lived before she and Harry dramatically stepped down as working royals. 

Since ‘Megxit’, the Duchess  has focused much of her energy on her solo business projects. 

In March 2024, she soft-launched American Riviera Orchard before changing the companies name to As Ever. 

Announcing the new venture, Meghan said: ‘This new chapter is an extension of what has always been my love language, beautifully weaving together everything I cherish – food, gardening, entertaining, thoughtful living, and finding joy in the everyday.’

The food products sold by the brand include an assortment of teas, edible flower sprinkles and a £20 jar of honey.

More recently, Meghan launched her latest line of products – Californian rosé wine. Customers were able to purchase three bottles for £66, six bottles for £118, and 12 bottles for £223 and it was sold out within the hour.

She has also invested in a number of companies including the vegan coffee brand Clevr Blends and haircare line Highbrow Hippie.

Meghan holds a briefcase on Deal or No Deal. Writing in his biography of the Duchess of Sussex, titled Meghan Misunderstood, royal author Sean Smith lifted the curtain on how Meghan made ends meet in Hollywood

Meghan holds a briefcase on Deal or No Deal. Writing in his biography of the Duchess of Sussex, titled Meghan Misunderstood, royal author Sean Smith lifted the curtain on how Meghan made ends meet in Hollywood

Meghan in 2009. Her most unusual job was as a calligrapher - a person who specialises in writing word in a beautiful, stylised way

Meghan in 2009. Her most unusual job was as a calligrapher – a person who specialises in writing word in a beautiful, stylised way

She has also invested in asset manager Ethic, which focuses on sustainable investments. 

Harry and Meghan signed a lucrative £18million deal with Spotify in 2020. However, despite it appearing to be a joint venture, the only show they produced was hosted by Meghan. 

In the series, titled Archetypes, Meghan interviewed various celebrities from Serena Williams to Paris Hilton. 

The deal was ‘mutually ended’ in June 2023 with sources claiming the music streaming giant did not see enough content to warrant the full payout.

Earlier this year, the duchess launched her Confessions of a Female Founder with Meghan podcast which saw the royal chat with female business owners from an array of successful companies.     

In a slight career change, Meghan also penned a children’s book in 2021 titled The Bench.

In a slight career change, Meghan also penned a children’s book in 2021 titled The Bench.

The book follows the relationship of a father and son through the eyes of the mother and received mixed reviews from critics. 

Meghan's new podcast is one of her latest solo business ventures

Meghan’s new podcast is one of her latest solo business ventures 

Prince Harry and Meghan on their wedding day in May 2018

Prince Harry and Meghan on their wedding day in May 2018

In her television projects, Meghan and Harry have worked together on a number of projects.

Although an official figure was never announced, Harry and Meghan’s deal with Netflix was allegedly worth around £80million and saw the couple produce multiple shows. 

In 2022, the first  Netflix series about the Sussexes, aptly named Harry and Meghan, was released. 

While it holds the record for the biggest debut for a Netflix documentary, it received mixed reviews.

The pair were also executive producers on the Polo sports documentary series, which followed athletes at the US Open Polo Championship. 

In 2023, Meghan did not join Harry as an executive producer on the Heart of Invictus series, although the duke and duchess did appear together during the show.

In 2022, the first Netflix series about the Sussexes was released. While it holds the record for the biggest debut for a Netflix documentary, it received mixed reviews from critics

In 2022, the first Netflix series about the Sussexes was released. While it holds the record for the biggest debut for a Netflix documentary, it received mixed reviews from critics

Meghan’s first major solo television project was her lifestyle programme called With Love Meghan, which saw the duchess team up with a number of famous guests to cook and create homeware products.

Harry was almost entirely absent from the series aside from a very brief cameo in the last episode.

A source from the show has since reported that neither Harry nor their children will appear in the next season of the show.

And while Harry and Meghan’s Netflix deal is reportedly ‘dead’ it is understood the next season of With Love Meghan will still air.   

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