Why Madonna, The Rolling Stones and Paul McCartney Could Be Grammy Dark Horses

New, acclaimed albums by The Rolling Stones, Paul McCartney and Madonna could all be Grammy contenders — but this isn’t 1987, the last and only time those three icons were all nominated for Grammys in the same year.

Fast forward nearly four decades and each of these artists’ well-received 2026 albums — Madonna’s club world ­manifesto Confessions II, The Stones’ rock and blues romp Foreign Tongues and McCartney’s folkie nostalgia trip The Boys of Dungeon Lane — are in the conversation for album of the year at the 2027 awards. But considering how the awards have evolved, is this a good year to be a legacy artist at the Grammys?

Twenty years ago, legacy artists went on a surprising run at the Grammys, with Herbie Hancock and Robert Plant & Alison Krauss winning album of the year in 2008 and 2009, respectively. (Those wins were somewhat controversial: Hancock’s album of Joni Mitchell covers, River: The Joni Letters, beat out Amy Winehouse’s Back to Black and Kanye West’s Graduation, while Plant & Krauss’ Raising Sand trumped Radiohead’s In Rainbows and Lil Wayne’s Tha Carter III.)

For legacy acts, this type of later career win can be especially meaningful. “For many artists, the Grammy remains the pinnacle of peer recognition,” says Helen Bruner, a Grammy-nominated recording artist (with Terry Jones), former Recording Academy national trustee and onetime president of its Philadelphia chapter. “An album of the year nomination can affirm that an artist with an extraordinary history is still creating work capable of moving the culture forward.”

In 2005, Ray Charles’ Genius Loves Company (the artist’s posthumously released album of high-profile collaborations) won album of the year over major projects by Green Day and Alicia Keys. Going back further, Steely Dan’s Two Against Nature and Bob Dylan’s Time Out of Mind both won the award long after the artists’ most prolific eras. Bruner posits that this recognition is particularly valuable when it comes at that late date, as it signifies that the artist is “still contributing, still evolving and still capable of shifting culture.”

Such nominations still happen, even if they haven’t recently yielded wins. In 2023, Swedish pop greats ABBA got a nod for Voyage, its first album of new material in 40 years, while classic ­crooner Tony Bennett got the nod in 2022 for Love for Sale, his second collaborative album with Lady Gaga.

But with a voting body that’s now younger and more diverse, the chances of legacy artists earning nods — much less winning — are slimmer than they once were. According to the Recording Academy, more than 3,800 music creators and professionals joined as part of the 2025 new member class (those eligible to vote for the 2026 Grammys), with 50% of that class ages 39 or younger, 58% being people of color and 35% identifying as women. As part of a continued effort to grow and diversify its membership, the academy extended invitations to more than 4,000 music creators and professionals for its 2026 new member class, who are eligible to vote for the 2027 awards. That has likely helped propel artists with younger-­skewing fanbases like Harry Styles, Bad Bunny and Billie Eilish to taking home the top prize in the 2020s.

“A younger voting membership will certainly decrease the dominance of older artists,” says Steve Greenberg, a 30-year voting member, a former member of the New York chapter’s board of governors and a two-time Grammy winner. “That’s probably a good thing, because it’s always good to make room for younger artists.”

Still, with nominations in the album of the year category directly determined by rank-and-file Grammy voters since 2021, when the academy disbanded its nominations review committees, the mass familiarity with The Stones, McCartney and Madonna may give them a competitive edge.

“Artists like these would be most likely to get nominated in an album category,” Greenberg says. “Especially album of the year, where you have people from every corner of the industry and every genre of music voting for the category. The only names everybody’s heard of might be the legacy artist.”

With the album of the year category expanding from five to eight nominees in 2019 (where it remains today, following a two-year bump-up to 10 in 2022 and 2023), artists with such broad recognition may simply have the statistical advantage in a more crowded field. “In some ways getting nominated is the hardest part,” Greenberg says. “Once you get ­nominated, you don’t need such an overwhelming percentage of the vote to win.”

But McCartney, Madonna and The Stones (who collectively have 124 nominations extending back to 1965) will be competing with some of today’s biggest hitmakers, most likely including some combination of Taylor Swift, Olivia ­Rodrigo, Olivia Dean, Bruno Mars, Noah Kahan, RAYE and Rosalía.

“Today, legacy artists exist alongside entirely new generations of superstars who are creating their own cultural moments,” Bruner says. “The voting body also spans generations, bringing different musical experiences and perspectives to the process. I think that makes the conversation more interesting. A legacy artist today isn’t simply being considered in the context of their history.”

Being a megastar for decades has its advantages, though: With their global visibility and sustained name recognition, Madonna, The Stones and McCartney have all gotten major rollouts and top-tier press around their new projects. “I’m sure that attention will help them in the race for a Grammy,” Greenberg says.

That said, The Stones and Madonna have actually only been nominated for album of the year once each — The Stones for Some Girls at the 1979 ceremony and Madonna for Ray of Light in 1999. McCartney has been nominated four times since The Beatles split up: in 1975 with Band on the Run (with Wings), in 1983 with Tug of War, in 1998 with Flaming Pie and in 2006 with Chaos and Creation in the Backyard.

The Stones received the formal lifetime achievement award in 1986, and McCartney received it in 1990. While it’s possible voters may see this year as the final opportunity to recognize these artists in their lifetimes (McCartney is 84, Mick Jagger is 83, Keith Richards is 82 and Ronnie Wood is 79), Madonna’s Confessions II seized the cultural conversation in a way the other two did not, debuting atop the Billboard 200 and making the 68-year-old the first artist to top the chart in the 2020s and three other decades. She was the big winner at the MTV Video Music Awards in September, taking home seven prizes including artist of the year; the Grammys wouldn’t exactly be going out on a limb nominating her for album of the year.

And while wins for legacy artists in previous years seemed like proof to some that the Grammys were out of touch, one for Madonna would be both a nod to a longtime icon and an acknowledgment of one of the year’s buzziest albums — arguably a double win for both Madonna and the academy itself.