Prince Harry, Duke of Sussex and sixth in line to the British throne, had slipped away from his fellow royals to meet with the queen of media.

In a London hotel room in 2018, Oprah Winfrey listened as the prince described his mental-health struggles as a member of the world’s most famous family. Even his trip that day to the hotel—through a back door, to avoid the paparazzi—was a reminder of the restrictions and constant scrutiny that he lived under.

It...

Prince Harry, Duke of Sussex and sixth in line to the British throne, had slipped away from his fellow royals to meet with the queen of media.

In a London hotel room in 2018, Oprah Winfrey listened as the prince described his mental-health struggles as a member of the world’s most famous family. Even his trip that day to the hotel—through a back door, to avoid the paparazzi—was a reminder of the restrictions and constant scrutiny that he lived under.

It was a deeply personal conversation, but the prince and Ms. Winfrey weren’t alone. Also in the room, sitting nearby but keeping quiet, was Jon Kamen, a New York-based film and television producer. To him it looked like something else: a hit.

“Guys,” he later told his producing partners, “the format of this show—we witnessed it in that hotel room.”

Nearly three years later, Mr. Kamen, the chief executive of RadicalMedia, would be wrapping up the Hollywood project that resulted from that meeting: “The Me You Can’t See,” a six-episode series on mental health released by Apple Inc. in May. A conversation between Prince Harry and Ms. Winfrey—not unlike that hotel room heart-to-heart—anchored every episode. Prince Harry co-produced the series and shared intimate details of the sweat-drenched anxiety attacks and profound sadness that he said gripped his time in the spotlight.

“I always wanted to be normal, as opposed to Prince Harry,” he says in the documentary.

If there was a moment when the scion of a tradition-bound dynasty bridged the gulf to his new life as a bare-it-all Hollywood producer, it may have been this: working with Oprah Winfrey on a TV show that mined his personal history for a streaming platform operated by the world’s richest company.

Since leaving behind their royal duties last year and moving to California, Prince Harry and Meghan, the Duke and Duchess of Sussex, have netted tens of millions of dollars in deals with media companies like Netflix Inc. and Spotify Technology SA, many of which rely on their proximity to their previous life in England.

Oprah Winfrey arrives at St George's Chapel at Windsor Castle before Prince Harry and Meghan Markle’s wedding in 2018.

Photo: Ian West/WPA Pool/Getty Images

Getting there has been no fairy tale. Interviews with associates and colleagues of the couple reveal years of behind-the-scenes hustling that laid the groundwork for a major Hollywood arrival that will blanket the couple across film, TV, podcasts and books. They mined personal connections and friendships. They met with potential suitors and evaluated streaming services for their ability to reach a global audience, securing a deal reported to be in the $100 million range from Netflix in the process. And they have frequently excavated their own personal lives to draw eyeballs, trying to wrest control of the narrative by lambasting critics and telling the story themselves.

In essence, to escape a life under the microscope, they chose a different microscope.

Mr. Kamen observed how, for Prince Harry, the Apple series wasn’t just a tour of his emotional past, even touching on the trauma of the death of his mother, Princess Diana, in a car crash when he was 12 years old. It was also an educational primer on the producing duties that may define his future.

Prince Harry joined Zoom meetings with Ms. Winfrey—first from England, then in Canada, and finally in Montecito, Calif. He shared with the series’ producers his contacts with the global elite to enlist more participants, and suggested the formation of an advisory board that helped the team navigate the sensitive topics they were exploring. He vetted the subjects and pushed to bring in interviewees from beyond the Western world. He watched early edits and turned in notes faster than Ms. Winfrey.

Streaming companies have spent generously for outsider producers like Barack and Michelle Obama and Pakistani education activist Malala Yousafzai, but skepticism is growing in the industry that big names translate into big profits. The Duke and Duchess’s deal includes shows that have little to do with their personal connections, raising a critical question: Does anyone care about them when they aren’t spilling the tea on the royal family?

Calling Hollywood

Prince Harry and Meghan, a former actor, started building their Hollywood Rolodex almost immediately after their May 2018 wedding—an event watched by 29 million people in the U.S. and attended by Ms. Winfrey.

They met with power brokers like Jeffrey Katzenberg, who contacted them to discuss a project that would highlight their philanthropic pursuits through his short-lived Quibi streaming service. Taking a meeting with the couple then often meant signing a nondisclosure agreement, according to those who met with them.

Meghan began a relationship with Netflix that same year, through a connection to her deceased mother-in-law. David Furnish, a Canadian filmmaker, wanted to produce an animated series with the Duchess. Mr. Furnish’s husband, the singer Elton John, had been close friends with Princess Diana.

In July, Netflix announced it was developing that idea into “Pearl,” a family show about a young girl whose adventures are informed by her interactions with famous women from history.

The prince also had a yearslong friendship with an industry heavyweight to lean on. He met Walt Disney Co. Executive Chairman Robert Iger at an overseas conference years ago, a relationship that has evolved into something of a mentor role since he moved to California, people close to the two men say.

One awkward example of how even those with royal lineage have to hustle in Hollywood came up in 2019, when Prince Harry and Mr. Iger had a mini-reunion on the red carpet at “The Lion King” premiere.

“You do know she does voice-overs?” Prince Harry asked Mr. Iger, gesturing to his wife in a video that circulated after the event. To outsiders, it appeared he was advocating for Meghan to get a job.

At ‘The Lion King’ premiere in 2019, Prince Harry pitched Robert Iger, then Disney’s CEO, while Meghan chatted with Beyoncé.

Photo: Niklas Halle/WPA Pool/Getty Images

“Ah, I did not know that,” Mr. Iger responded. He turned toward his own wife with a smile while Meghan chatted with Beyoncé and Jay-Z on his other side.

“You seem surprised,” Prince Harry said. “She’s really interested.”

Mr. Iger turned serious. “We’d love to try. That’s a great idea,” he said.

A year later, Meghan did voice-over work that associates say had already been planned for “Elephants,” a Disney documentary that the couple had seen filming during an earlier visit to Botswana. When the movie premiered on Disney’s flagship streaming service, Disney+, her involvement drew greater than usual media coverage for a nature documentary.

But the Disney team also grew privately concerned that critical tabloid reports about Meghan would depress viewership in the U.K.—a signal of the challenge of working with a producer better known for her personal life.

Buckingham Palace had no issues with such entertainment projects, which had a philanthropic or advocacy purpose, according to people familiar with the matter. Once the couple left the palace—in part due to personal tensions and constant scrutiny from British tabloids—they were able to pursue more commercial work.

Touchdown in L.A.

Soon after their arrival in Los Angeles in March 2020, the couple crashed at the 25,000-square-foot Beverly Hills home of director Tyler Perry before settling in Montecito, not far from Ms. Winfrey’s mansion. They hired an attorney who had worked on big-ticket streaming deals. For the Duchess, who had worked as Meghan Markle, it was a return to the Hollywood scene she’d known since nearly birth.

Her father, Thomas Markle, was a lighting designer in Los Angeles, and she would often joke that she grew up on the set of the bawdy 1990s sitcom “Married…With Children,” visiting her father after school.

While attending Northwestern University, she studied abroad in Argentina and interned for the U.S. Embassy. She thought she would go into politics. Instead, she went into her hometown industry, booking parts like “hot girl” in the 2005 Ashton Kutcher rom-com “A Lot Like Love” and appearing as Briefcase Model #11, Briefcase Model #12 and Briefcase Model #24 on the game show “Deal or No Deal” from 2006 to 2007. She called the show her “very lucrative waitressing job,” and made ends meet by doing calligraphy for celebrity wedding invitations.

Meghan Markle, center, on ‘Suits.’

Photo: Frank Ockenfels/NBC/Getty Images

Her breakthrough was in the summer of 2011, with USA Network’s “Suits,” a show about an unlicensed attorney who starts working at a law firm. The Duchess was cast as Rachel Zane, a sharp paralegal trying to get into law school. By the show’s second season, more than 3 million viewers were tuning in each week.

“Suits” gave Meghan a platform to explore some of the priorities she’d had outside of show business, traveling to South Carolina to hear the stories of high-school students who overcame bullying and bigotry. By 2014, she was speaking out for gender equality and attending events at the United Nations.

Meghan said she wanted to move behind the scenes after she got married. She has said, in subsequent interviews, including a headline-generating sit-down with Ms. Winfrey that aired on CBS earlier this year, that the tabloids’ prying into her personal life drove her to depression and suicidal thoughts.

The couple’s biggest draws in Hollywood have relied on those personal details—in the interviews with Ms. Winfrey; a podcast about how they and friends spent the pandemic, the sole result so far of a Spotify deal reportedly worth around $20 million; and a book deal with publisher Penguin Random House said to be worth around $20 million that was announced in July and will include the prince’s personal memoir.

The boy who saw his mother die because of the camera’s glare, said “Me You Can’t See” producer Mr. Kamen, “understands the power of media.”

Prince Harry and Meghan’s interview with Ms. Winfrey in March made headlines in British newspapers.

Photo: Chris Jackson/Getty Images

The talks

In Hollywood, the prince has tried to expand his output beyond the personal, casting himself as a next-generation David Attenborough, the nature documentarian famous for films like “Planet Earth.” He already has experience in that realm, working on a 2018 documentary about saving rhinos from dehorning practices called “Stroop: Journey into the Rhino Horn War.”

The Duke and Duchess hit the market during a rush that turned into streaming-service FOMO—fear of missing out on the producer who would deliver a breakthrough hit. For streamers competing against one another, getting J.J. Abrams, the Obamas or any other notable name signed was as much about bringing them in-house as it was keeping them out-of-house elsewhere.

Though they had scant producing experience, Prince Harry and Meghan had a few advantages. They are globally recognized names at a time when streaming services are competing for viewers around the world. They are a young family at a time when most megadeal signers are midcareer professionals, making them a potential draw for younger audiences absorbed in TikTok and other services.

The couple’s lawyers set up meetings with companies only after conveying the range of investment they were looking for, hoping to avoid putting the couple through talks that were just about meeting the famous pair. Disney, Netflix, Apple and NBCUniversal were among those who met with the couple or their team.

Netflix won, signing their Archewell Productions, a division of their company formed last year and named for the Greek word “arche,” which means “source of action” and served as inspiration for their son Archie’s name.

“Through its creative partnership with Netflix, Archewell Productions will utilize the power of storytelling to embrace our shared humanity and duty to truth through a compassionate lens,” the company said when the deal was announced.

Ms. Winfrey interviews the Duke and Duchess.

Photo: Joe Pugliese/Harpo Productions/REUTERS

Netflix wasn’t the highest bidder, according to a person familiar with the matter, but the couple was drawn to the service’s global footprint, its focus on children’s programming and the menu of other shows it could carry, from documentaries to scripted series.

The deal came just as skepticism across the industry was growing over such arrangements. Studios fell over themselves to woo creators like Mr. Abrams in deals worth hundreds of millions of dollars, but only a few such arrangements have yielded commensurate hits. And even as Netflix talent deals produce home runs like Shonda Rhimes’s “Bridgerton,” many of the service’s breakout shows have also come from relatively unknown creators, with programming like “The Tiger King” and “The Queen’s Gambit.”

Archewell is also competing for growing interest in royal-family programming. Netflix’s fourth season of “The Crown,” about the life of Prince Harry’s grandmother, won outstanding drama series at the Primetime Emmy Awards on Sunday. Actress Kristen Stewart is generating awards buzz for her turn as his mother in the coming movie “Spencer.” Princess Diana is even getting the musical treatment in a show called “Diana,” slated to open on Broadway in November.

Prince Harry and Meghan have spent the past several months hiring executives like podcast veteran Rebecca Sananes as head of audio, joining a handful of employees.

She reports to Ben Browning, Archewell’s head of content, who was hired in March. Mr. Browning earned acclaim most recently for co-producing “Promising Young Woman,” a revenge fantasy about surviving sexual assault that was nominated for best picture this year at the Academy Awards.

Prince Harry and Meghan Markle are the latest British royals to seek more financial independence from the monarchy. WSJ explains why, like other family members before them, they weren’t allowed to pursue private ventures while also doing business within “the firm.” Photo illustration: George Downs The Wall Street Journal Interactive Edition

Now Mr. Browning is heading a company that will, in its words, “share impactful content that unlocks action.”

So far, that has meant safe, feel-good programming.

Archewell isn’t going to produce the next “Chucky,” as one business associate described it, but the team is trying to avoid programming that seems overly earnest.

Any production will have a hard time outshining the books and interviews that have broken the seal of custom and reserve that define the royals. In “The Me You Can’t See,” Prince Harry spoke of recalling the sound of horse hooves from his mother’s funeral. He talked of Meghan crying at night because of the cruelty of the London tabloids, and how his son said “Grandma Diana” from an early age. And most notably, in a separate interview with Ms. Winfrey, the couple shared the bombshell that an unidentified member of the royal family openly speculated to Harry on the skin tone of their child.

It’s undeniably good TV, but it also means the Sussexes bring a unique set of baggage to a working relationship. While producing “The Me You Can’t See,” Mr. Kamen was approached by the producers of the Broadway musical “Diana.” It was being filmed for release on Netflix—the kind of adaptation Mr. Kamen’s company had done to great acclaim with the blockbuster musical “Hamilton.” He passed on the opportunity, worried that Prince Harry would be angry with him if he got involved with a show about his mother.

Mr. Kamen never mentioned to Prince Harry how he had passed on the project, but now he doesn’t know if the prince would have cared. After all, the prince and his wife soon signed their own deal with Netflix.

—Max Colchester contributed to this article.

Write to Erich Schwartzel at erich.schwartzel@wsj.com