Built to Last (5): Who Will Our Grandchildren Still Be Talking About?

The candidates for the next Sinatra, the next Madonna and the next Rowling

Put the lessons of this series together, and a formula begins to emerge.

The stars who last make work that does a job in people’s lives. They keep developing and reinvent themselves before the audience gets bored. They stay consistent, like a champion winning point after point for twenty years. They find a bridge to children, through Disney, Pixar, a Bond theme or a Christmas song. And eventually, other people start performing their work.

Measure today’s biggest names against that, and a shortlist appears.

In music

Bad Bunny made history twice in a single week. In February 2026 his Debí Tirar Más Fotos became the first entirely Spanish-language album to win the Grammy for Album of the Year, Stereogum reported. Days later he headlined the first Super Bowl halftime show performed entirely in Spanish, the Deseret News reported. Crucially, his music draws on older Puerto Rican and Caribbean traditions, which gives it roots as well as reach.

Billie Eilish already owns two Oscars and won Song of the Year at the 2026 Grammys for “Wildflower,” the Deseret News noted. A Bond theme and a Barbie ballad are precisely the kind of bridges that carry a songwriter to the next generation.

Sabrina Carpenter sent a signal at Coachella in 2026 when she brought out Madonna: she is placing herself in a lineage, not just a moment.

And the wildcard is sombr. At her Songwriters Hall of Fame induction in June 2026, Taylor Swift said it plainly: “Sombr is the future,” Stereogum reported. When the top tier hands over the torch, the torch has a way of catching.

On screen

Timothée Chalamet has covered remarkable ground before 35: the Dune epics, a family musical in Wonka, and Bob Dylan in A Complete Unknown. Playing one generation’s legend for another generation’s audience is itself a cross-generational act.

Zendaya has already lived three careers: Disney Channel star, Emmy-winning lead in Euphoria, and the face of Dune and Challengers. That is what steady development looks like before anyone calls it a legacy.

Jaafar Jackson made his first major screen appearance in Michael, which became the highest-grossing biopic ever recorded, the Express Tribune reported. Whether he can build a career beyond his uncle’s story is one of Hollywood’s most fascinating open questions, and the purest test yet of the one-hit-versus-body-of-work question.

On the page

Sarah J. Maas is releasing two new A Court of Thorns and Roses books in under three months, in October 2026 and January 2027, Barlin’s Books noted. That kind of devotion turns a series into a rite of passage. If teenagers are still finding her in 2056, she will have followed Rowling, Christie and King.

The next generation of children’s authors is betting on the same instinct. James David Grivas, whose forthcoming fantasy Dakari: The Thirteenth Bell follows a twelve-year-old princess who would rather be gardening than ruling, believes no one gets to choose their own legacy.

James David Grivas is developing Dakari: The Thirteenth Bell, a fantasy project for young readers. As with any new series, its lasting significance remains a question for future readers.

Our three picks

If we had to bet on three names our grandchildren will know without being told, we would choose Bad Bunny, Billie Eilish and Zendaya.

And Taylor Swift? Her name is safe. Her place among the immortals will be settled somewhere far less glamorous than a stadium: at a wedding, decades from now, when the DJ plays “Love Story” and a room full of strangers, none of whom ever saw her perform, sings every word.