The next morning, Hugo and Joseph got up at nine, quickly prepared themselves, and set off on foot toward the Loop commercial district, less than two miles away.
The Loop is not only Chicago's traditional central business district but also the second-largest CBD in the United States, after Manhattan. Its importance extends beyond the U.S.—Michigan Avenue owes its global fame in no small part to the Loop, often compared to Paris's Champs-Élysées.
Harpo, the production company founded by Oprah Winfrey, is located right in the heart of the Loop. Walking along Washington Street, one could catch a distant glimpse of the United Center, home of the Chicago Bulls. But Hugo and Joseph paused at the intersection with Madison Street, feeling the gentle breeze from the Chicago River behind them, and gazed at the gray-bricked buildings ahead, roughly thirty stories tall. Among the surrounding skyscrapers, they seemed unremarkable, almost like an ugly duckling—but it was here that a show would be nurtured to dominate American talk television for over a decade.
Harpo Productions, established in 1986, initially owned and produced only The Oprah Winfrey Show. Its operations were modest, yet Hugo knew this unassuming company had leveraged the show to grow steadily. By 1996, it had transformed into a large entertainment conglomerate with divisions in talk shows, film, radio, print, and digital media—a classic ugly duckling-to-swan success story.
Once inside the building, Hugo and Joseph registered at the front desk and received temporary visitor passes. Before they could even reach the elevator, someone came down to greet them, warmly welcoming Hugo for the taping while apologizing again for missing the airport pick-up the day before. They then led Hugo and Joseph to the studio. Even this small detail reflected how much the production team valued Hugo, giving him a ceremonious reception.
Compared with the studios Hugo had previously visited for other show tapings, The Oprah Winfrey Show felt modest. Because production was fully controlled in-house, the budget was limited, and the studio equipment appeared simple. The so-called studio was a warehouse-sized space with various backdrops, two large red armchairs at the front, and four cameras along with a crane camera overhead. Near the entrance was a small audience section, accommodating around 150 people, reminiscent of outdoor bleachers at a high school football game.
As soon as Hugo entered the green room, Oprah herself came out to greet him. The talk-show queen, not yet forty, wore a retro '90s updo reminiscent of a conch shell, and her broad smile radiated warmth. Her robust frame was more endearing than graceful, and her thick lips curved into a kindly arc, instantly putting people at ease.
"It's truly an honor to have you here. Thank you so much for coming to Chicago on such short notice," Oprah said, embracing Hugo warmly.
Hugo returned the smile. "Of course. Being invited to The Oprah Winfrey Show, no matter the distance, I had to come. This is such a rare opportunity, and I'm grateful for the invitation."
Oprah released him and subtly assessed the young man before her. Hugo was dressed casually in a simple T-shirt and jeans, looking like any young adult just starting out. Yet his smile rivaled the sunshine outside, and his striking features were so precise it was as if a painter had captured them in perfect strokes.
Oprah had already seen A Few Good Men , where Hugo, in his naval uniform, exuded charisma that could melt countless hearts. She had prepared herself for his good looks, yet seeing him in person still caused a brief pause. Unlike the commanding presence in the film, this Hugo radiated sunshine—a gentle warmth and brightness that was impossible to look away from.
"I'm really looking forward to our conversation today. I hope this will be a memorable experience," Oprah said, her professional composure returning quickly. "Oh, and congratulations on your double Golden Globe nominations—well deserved."
With that, she politely left the green room, giving Hugo space to prepare.
Hugo settled at the makeup table, waiting for the Oprah Winfrey Show team to style him. In Hollywood, true A-list stars often have their own personal teams. Beyond assistants and managers, security, makeup artists, hairstylists, and stylists are long-term collaborators, especially during press-heavy periods.
The very top stars can afford exclusive teams, paying their salaries indefinitely, but most actors share a fixed team that may also serve other clients. Even the most sought-after makeup artists, hairstylists, and stylists usually have studios or agents, making the field highly specialized yet professional. So, if an actor wants a reliable team but cannot afford exclusivity, they must rely on their agent's connections and pre-scheduled appointments.
In simple terms, every top-tier actor has a dedicated team tailored for each public appearance.
For a premier show like The Oprah Winfrey Show, it naturally maintains its own in-house team. Since the show tapes weekly, the team primarily serves the program—though a single team might work on two or three shows, their main responsibility is television production. Compared to private celebrity teams, TV show teams are somewhat less specialized. One reason is that most guests are ordinary people, and professional actors come with their own teams, so the technical demands are lower. Another reason is time constraints—there's limited opportunity to craft individualized looks for every guest.
This isn't to say the TV team is unskilled, just that their professionalism differs from that of top-tier personal teams.
After the success of the A Few Good Men , Hollywood began treating Hugo like a first-tier actor. But what does it mean to be "A-list"? Hollywood has many metrics. First, pay scale: in the early '90s, earning $8 million per film qualified an actor as top-tier; $10 million marked a higher echelon, and $15 million was extraordinarily rare.
Second, the size of the actor's support team. People joked that the bigger the entourage, the bigger the star. While partly humorous, some top stars embraced this, using massive teams as a status symbol. For instance, around 2000, Mariah Carey had a twenty-plus member team, and every outing was a grand procession. A complete team is undeniably essential for elite actors.
Though many now considered Hugo an A-list actor based on box office and popularity, this was still speculative. Some believed he could command $8 million per film, but until a studio actually offered that, he couldn't claim official A-list status.
Hugo's current promising projects included the no-audition film The Firm and the tentative Sleepless in Seattle. For The Firm, $8 million was plausible depending on the audition outcome; for Sleepless in Seattle, reaching that figure seemed unlikely. So Hugo would have to wait a bit longer before officially joining the A-list.
As for his personal team, Hugo was still woefully under-equipped, with only Joseph supporting him. Not long ago, Joseph had advised Hugo to hire an assistant or manager—not because Hugo was A-list yet, but because the workload was simply too large for one person. Building a proper team wasn't easy, especially with everything happening so quickly, so Hugo would have to wait until things settled before assembling one.
In essence, Hugo's fame was already first-tier, but his support system was still second-tier. At The Oprah Winfrey Show, he came unprepared, relying entirely on the show's makeup and hairstyling team. Fortunately, Hugo's look required minimal effort, and his hairstyle was simple, so the in-house team could manage without issues.
Once Hugo finished getting ready and changed into his stage outfit, the production staff briefly explained the recording schedule. Usually, The Oprah Winfrey Show is divided into two parts: the first half discussing trending topics, and the second half featuring guest interviews. However, to show their respect for Hugo—and with Joseph's approval—both halves would be dedicated entirely to him. This allowed for a comprehensive interview and exploration of Hugo's persona, making it the most high-profile program he had done in two months.
Hugo felt a pang of anxiety. He still lacked full knowledge of his past work and hoped he wouldn't be caught off guard by Oprah's questions. But with no choice but to go forward, he took a deep breath, calming his nerves and preparing himself for the recording.
....
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