By JT Santana | jtwb768

Which celebrity would you love to meet, and what would you talk about?

Some people become famous for what they accomplish. Others leave something behind that continues to challenge us long after their voices have gone quiet. The people I would most love to meet are not necessarily the ones who dominated television screens, sold millions of records, or collected the most awards. I am drawn to people who made others think, challenged expectations, refused to become smaller to accommodate the people around them, and used their talents to say something meaningful about the human experience.

Two people immediately come to mind: artist Keith Haring and entertainer, activist, and unapologetic truth-teller Eartha Kitt. They came from different backgrounds, worked in different artistic disciplines, and occupied different places in American popular culture. Yet both possessed something I admire deeply: the willingness to challenge the assumptions of their time rather than simply accept the world as it was presented to them.

There is a personal dimension to my answer, too. I had the privilege of knowing Keith Haring. Meeting him again, with the perspective that comes from living through decades of social change, would be an extraordinary opportunity. Eartha Kitt is someone I would have loved to meet, sit with, and listen to for hours. My conversations with these two remarkable people would be different, but both would revolve around art, courage, identity, power, and the price people sometimes pay for telling the truth.

Keith Haring: The Conversation I Would Have Today

Keith Haring occupies a special place in my life, and my interest in him extends far beyond his extraordinary artwork. Our connection began in 1989, when he worked on a school mural in Iowa City. We remained in contact until the day before his death in February 1990. That history makes this answer personal in a way that a list of favorite celebrities could never capture.

I would love another conversation with Keith, not because I need to ask him how he became famous, but because I want to know what he would make of the decades that followed his death. He created art that was accessible, recognizable, and frequently joyful, yet his work confronted serious subjects, including racism, homophobia, violence, AIDS, and the abuse of power. He understood that art could reach people who might never enter a museum or pick up a book about social justice.

My first question would be about the AIDS crisis and the years of activism that surrounded it. What would he think about the medical advances that transformed HIV from a frequently fatal diagnosis into a manageable chronic condition for many people with access to treatment? What would he say about the continuing stigma, the unequal access to healthcare, and the way public attention can fade even when the people affected by an epidemic are still living with its consequences?

I would want to talk about the people we have lost, too. Keith died at 31, at a time when the epidemic was devastating communities and government responses were painfully inadequate. His death was a personal loss for the people who knew him, but his legacy belongs to a much larger history of art, activism, and resistance.

I would ask him whether he believed his art had changed anything, and how he measured the distance between raising awareness and achieving actual change. Did he ever worry that institutions would embrace his imagery and commercialize it without embracing the values behind it? How would he respond to a society that can sell an artist’s image on a T-shirt while ignoring the people and struggles that gave the image meaning?

I suspect we could talk for hours about the difference between being visible and being heard. Visibility can be profitable, fashionable, and temporary. Being heard requires someone to take your message seriously, even when that message makes them uncomfortable.

Most of all, I would want to tell Keith what his work and his example have continued to mean to me. Sometimes we do not fully appreciate the significance of a person or a moment until time gives us a longer view. I would not waste our conversation pretending I had all the answers. I would listen, challenge him, laugh with him, and ask what he thought we still had not learned.

Eartha Kitt: The Woman Who Refused to Make Herself Smaller

If Keith represents a conversation I would cherish having again, Eartha Kitt represents a conversation I wish I could have experienced at least once.

Kitt was an accomplished singer, actress, dancer, and activist whose distinctive voice and commanding presence made her impossible to confuse with anyone else. She possessed extraordinary stage charisma, but her legacy is not simply about entertainment. She challenged expectations about race, gender, sexuality, power, and the roles women were expected to play in public life.

She also demonstrated that speaking truth to power can carry real consequences. In 1968, during a White House luncheon hosted by First Lady Lady Bird Johnson, Kitt spoke against the Vietnam War and raised concerns about the impact of the conflict on young Americans and their families. The episode damaged her career in the United States for years, illustrating the cost that can accompany dissent when influential people would prefer silence.

That is where I would begin.

I would ask her whether she knew, at that luncheon, how dramatically her words might affect her professional life. Did she consider remaining silent? Did she believe she had a responsibility to speak, regardless of the consequences? What did she learn about the relationship between political influence and the entertainment industry after powerful people decided that her criticism was unwelcome?

I would want to hear her thoughts about women who are praised for being outspoken until their words challenge someone important. Society often celebrates a strong woman in theory, then punishes her when she demonstrates strength in practice. The same public that admires independence can become deeply uncomfortable when a woman refuses to be managed, softened, or instructed to stay in her place.

Kitt understood that contradiction.

I would ask how she maintained her sense of self in an industry that frequently expected women, particularly Black women, to fit narrow and convenient roles. How did she protect her individuality when others wanted to turn her into a marketable character? What advice would she offer a young person who knows what they believe but fears the personal cost of saying it aloud?

I would want to discuss activism, too. Is there a point when speaking out becomes more important than preserving a career? How does someone distinguish a principled stand from a performance intended to attract attention? What responsibilities accompany the privilege of having an audience?

I would not assume that every answer would be comfortable. In fact, I would hope she challenged me as much as I challenged her. A meaningful conversation with someone like Eartha Kitt would not be an exercise in collecting inspirational quotations. It would be an opportunity to examine the compromises people make, the courage they summon, and the moments when silence becomes its own kind of decision.

What These Two People Have in Common

Keith Haring and Eartha Kitt remind me that creative achievement and public responsibility do not have to exist in separate compartments. Their work reached audiences through different channels, but both used their visibility to engage with issues that extended beyond personal success.

Neither person’s legacy can be reduced to a simple lesson about courage. Haring’s art emerged from a specific historical moment shaped by urban culture, queer communities, and the AIDS crisis. Kitt’s experiences reflected the racial and gender barriers of the entertainment industry, along with the political pressures surrounding dissent during the Vietnam War. Their lives deserve to be considered in their own historical contexts rather than converted into convenient symbols.

Yet their examples invite a question that remains relevant: What do we do when our values conflict with the expectations of the people who hold influence over us?

For writers, artists, advocates, and ordinary people, the answer is rarely simple. Speaking honestly can cost relationships, opportunities, income, or public approval. Remaining silent can carry its own costs, particularly when silence leaves misinformation unchallenged or vulnerable people without support.

I have spent much of my life interested in the places where personal experience intersects with public responsibility. That is part of why these two people stand out to me. They remind me that a person’s work can entertain, provoke, educate, and leave behind questions that remain relevant long after the original moment has passed.

The Questions I Would Carry Into Both Conversations

If I had the opportunity to sit with Keith Haring and Eartha Kitt today, I would not spend the entire time asking about their careers. I would ask what they had learned about people, what they regretted, what surprised them, and what they believed future generations were getting wrong.

I would ask Keith what he would paint on a wall in 2026, and what message he would refuse to let the public overlook. I would ask Eartha what she would say to political leaders who mistake agreement for loyalty and criticism for disloyalty. I would ask both whether they believed we had become better at listening to uncomfortable truths or simply more skilled at turning them into entertainment.

Their answers would be fascinating, but the opportunity to ask those questions would be just as valuable.

Meeting a celebrity can be an exciting experience. Meeting someone whose work and choices have shaped how you think about life, however, offers something different. It creates an opportunity to revisit your own beliefs, reconsider old assumptions, and learn from a person whose experiences extend beyond your own.

Keith Haring is someone I was fortunate enough to know, and that connection will always remain part of my story. Eartha Kitt is someone I wish I could have met, not merely to tell her how much I admired her, but to hear how she understood the world she inhabited.

If I could spend an afternoon with either of them, I would arrive with questions and leave hoping I had acquired a few more. I would want the conversations to be honest, occasionally uncomfortable, intellectually challenging, and full of the kind of laughter that comes from being able to speak freely.

That would be the real gift: not meeting a celebrity, but spending time with two people who remind us that a life can be measured by more than recognition. It can be measured by the questions we ask, the truths we are willing to speak, the people we stand beside, and what we leave behind for others to carry forward.