The Dream Costs. Just Ask Basquiat

By Theresa Rézeau

There are no shortcuts to a dream life. Not for those who become icons, nor for those who leave behind legacies etched in brushstrokes, businesses, or bloodlines. If we could ask Jean-Michel Basquiat, he might have told us that greatness is paid for in full , often too soon, often in silence.

He was young. Relentless. Electric. The kind of brilliance you don’t cultivate,  you survive it. Before he became one of the most celebrated artists of the 20th century, Basquiat was a teenage runaway sketching anatomy on torn pages and tagging walls under the moniker SAMO. He moved through the New York underground like a phantom: couch to couch, club to club, canvases stashed beneath the weight of rejection and resolve.

He was radiant, Black, and uncontainable, a trifecta that the art world, still trembling under its own elitism, didn’t know how to embrace. He found a strange kinship in Andy Warhol and a deep creative brotherhood in Keith Haring. His relationships burned hot and fast, including an early, stormy romance with Madonna, long before either of them became mythic. These bonds shaped him, yet they couldn’t save him.

In May 2017, Jean-Michel Basquiat joined “the pantheon of great, great artists” when his 1982 work Untitled sold for a record-breaking $110.5 million at auction, the highest sum ever paid for a U.S.-produced artwork. That breathless assessment was offered by Oliver Barker, chairman of Sotheby’s Europe. So you can imagine just how thrilled the buyer, Japanese billionaire Yusaku Maezawa, must have been. A price like that doesn’t just celebrate an artist. It cements him in the firmament.
(Jean-Michel Basquiat, Untitled, 1982: Photo by Sotheby’s)

But Basquiat never lived to witness his ascension. He died at 27, haunted by heroin and the isolation that genius so often invites. He left no children. No final interviews. Just pigment and pain, frozen on canvas.

And yet, across time and genre, a woman born in Barbados, thousands of miles from New York’s SoHo, began scripting her own version of legacy. Rihanna. Bad Gal. Billionaire. Matriarch.

Her story couldn’t be more different and yet, spiritually, it rhymes. She, too, came from nothing. She, too, understood that the world doesn’t reward you for being talented, it rewards you for being unstoppable. From dropped record deals to global superstardom, from music mogul to Fenty Beauty’s visionary, Rihanna built her empire not just with beauty, but with brutal focus. Every shade of foundation. Every brand partnership. Every silence between albums. It’s all strategy. All signal. No noise.

Where Basquiat painted his truth, Rihanna embodied hers. She moved from muse to mogul, from cover girl to culture-shifter. And unlike Basquiat, she is building a family alongside her fortune. Children in tow. Generational wealth in hand. A living legacy. But make no mistake, she, too, has faced the crucible. Public heartbreaks. Creative burnout. Scrutiny that tried to shrink her. Like Basquiat, she refused to make herself smaller. She refused to give up.

Because that’s what the dream demands: the resilience to rise when no one’s watching, the courage to bet on yourself before anyone else does. Basquiat knew it. Rihanna lives it. In the end, legacy is not a byproduct of luck. It is a luxury earned by endurance. A kind of beauty far deeper than aesthetics, the kind you pay for with everything you’ve got. 

And so, for those chasing the dream life, pause before you ask for the glow. Ask instead: am I willing to walk through the fire for it?

If only we could ask Basquiat.