Hollywood is a fickle place. One day you're the "It" girl, the next you're a footnote in a Wikipedia article about 90s fashion trends. But when you look at the heavy hitters—the people who actually have staying power—it's wild how many of them share a first initial.
I’m talking about the W club.
It’s not just a random letter. Think about it. Will Smith, Winona Ryder, Wendy Williams. These aren’t just names; they’re eras. They’re brands. Some are mounting massive comebacks in 2026, while others are fighting for their literal freedom. Honestly, the drama surrounding celebrities that start with W is usually way more interesting than whatever is happening with the rest of the alphabet.
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Let's get into what’s actually happening with these icons right now.
Will Smith and the Art of the Pivot
Will Smith is basically the final boss of Hollywood. Just when you think he’s done, or he’s retreated to some quiet life after a scandal, he pops back up with something absolutely massive.
Right now, in 2026, he’s not doing another Bad Boys (well, okay, there’s always talk about that). He’s doing something way weirder. Have you heard about Pole to Pole? It’s this National Geographic series where he literally travels from the South Pole to the North Pole.
It took five years to film.
Imagine Will Smith, the guy from Independence Day, skiing across Antarctic ice fields and milking venomous tarantulas in the Amazon. It’s a lot. He’s been out in Dubai recently promoting it at the SEE Institute—the region's first net-zero building. It’s clear he’s trying to shift his legacy toward "global explorer" and away from "guy who did that thing at the Oscars."
But let’s be real. We still want to see him in movies. Luckily, he’s got I Am Legend 2 and a Netflix thriller called Fast and Loose on the horizon. The man doesn't sleep.
The Winona Ryder Renaissance
If Will Smith is the king of the W’s, Winona Ryder is the patron saint of the "cool kids."
She’s always had this ethereal, slightly haunted vibe that Gen Z has absolutely latched onto. Between the Beetlejuice Beetlejuice craze and the final chapter of Stranger Things, Winona is everywhere.
Wait. Did you see the A$AP Rocky music video?
In early 2026, she showed up in Rocky’s "Punk Rocky" video. She’s playing a neighbor, wearing a Beavis and Butthead shirt, eating blueberries. It’s so peak Winona. It’s that effortless "I'm not trying to be a celebrity" energy that makes her so much more likable than most of the people on TikTok.
She reminds us that you can disappear for a decade, come back, and still be the most interesting person in the room.
Wendy Williams: The Battle We Can't Ignore
We have to talk about Wendy. Honestly, it’s heartbreaking.
While other celebrities that start with W are winning awards or traveling the globe, Wendy Williams is in a literal fight for her life and her bank account. As of 2026, she is still under a legal guardianship.
If you haven't been following the court docs, it’s a mess. Her guardian, Sabrina Morrissey, has been in charge of her health and finances since 2022. Wendy, meanwhile, has been vocal—well, as vocal as she can be—about wanting out. She famously called her facility a "luxury prison."
In July 2025, she made a rare appearance at Columbia University looking surprisingly sharp. She was wearing a Gucci belt and her signature "W" pendant. Fans are still rallying for her, especially after her family and her ex-husband, Kevin Hunter, started challenging the guardianship in court.
It’s a complicated situation. You have the medical diagnosis (frontotemporal dementia and aphasia) on one side and her personal pleas for freedom on the other. It’s a reminder that the "W" in Wendy stands for "warrior," whether she’s on a purple chair or in a courtroom.
Why the Letter W Matters (Seriously)
Is there something about the letter W? Probably not scientifically, but culturally? Absolutely.
- The Name Recognition: W names often sound punchy. Willem Dafoe. Whoopi Goldberg. Wes Anderson. They stick.
- The Longevity: Look at Woody Harrelson. The guy has been consistently working since Cheers.
- The Variety: You have the quirky (Wes Anderson), the legendary (Whoopi), and the rising stars like Wolfgang Novogratz.
It’s a diverse group. You’ve got Wiz Khalifa holding down the music side and Wunmi Mosaku killing it in prestige TV.
What You Should Watch (and Follow) Next
If you’re trying to keep up with the "W" crowd, don't just scroll Instagram. Most of the real action is happening on the screen or in the trades.
- Check out Will Smith’s "Pole to Pole" on Disney+. It’s genuinely beautiful and makes you feel like you’re actually doing something with your life, even if you’re just sitting on the couch.
- Track the Wendy Williams court updates. The next big hearing regarding her guardianship status is something everyone in the industry is watching. It could change how conservatorships are handled in New York forever.
- Keep an eye on Winona’s indie projects. Beyond the blockbusters, she usually has a few small, weird films in the works that remind you why she was the face of the 90s.
Hollywood is changing. The way we view celebrities is more about their personal struggles and their "realness" than their red carpet looks. Whether it’s Will Smith facing his fears in the Arctic or Wendy fighting for her rights, these celebrities that start with W are proving that they aren't going anywhere.
They’re messy, they’re talented, and they’re consistently the most talked-about people in the room.
To stay ahead of the curve, keep an eye on the 2026 festival circuits. Names like Wes Anderson are already being floated for major fall premieres, and the "W" legacy is only getting stronger.