(December 14, 2025) – Back in the late 1990s, it was common to see artists from a quarter century earlier still having success on the Billboard charts. Huge success even.
Cher had the biggest hit of her career (“Believe”) in 1999, more than 25 years after her prior No. 1 and nearly 34 years since her first chart topper with late ex-husband Sonny Bono (“I Got You Babe” in 1965).
Similarly, superstar Elton John had scored the biggest hit of his career in 1997-98 with the two-sided “Candle in the Wind”/“Something in the Way You Look Tonight,” which came 27 years after his breakthrough single “Your Song” in 1970. Elton was still a regular chart fixture in the late 1990s having scored at least one top 40 single every year for 30 years straight.
Cher and Elton weren’t alone. Twenty-five-year-plus rock veterans like Aerosmith and Santana were racking up hits with regularity in the late ‘90s and early 2000s. The Boys from Boston — like Cher and Elton — scored their biggest hit, “I Don’t Want to Miss a Thing,” in 1998, more than 25 years after their chart debut in 1973 (“Dream On”). Santana — the band led by Carlos Santana — scored its two biggest hits with “Smooth” and “Maria, Maria” beginning in 1999. The back-to-back hits racked up a total of 22 weeks at No. 1 on the Hot 100. The band had been charting for more than 30 years at that point.
But one look at the charts from 2000-01 and the acts who were dominating them — or even simply appearing on them — and you’d be hard-pressed to find any artists from that period who are still achieving success on the Hot 100 today. Not just huge success like the aforementioned acts who achieved their biggest hits more than a quarter century into their careers, but any singles chart success.
Excluding holiday recurrents by artists like Mariah Carey (she’s been charting since 1990), none of the songs that reached the top 40 this year are by artists who were charting at the turn of the century. Veteran acts from that time aren’t just failing to get big hits, they’re not hitting at all.
Remember names like Savage Garden, Destiny’s Child, Matchbox 20, Third Eye Blind, Jewel, Goo Goo Dolls, Train, Creed, Nickelback, Faith Hill, and Shaggy? How about Usher, Brian McKnight, Joe, Sisqo, Jagged Edge, or TLC? Or what about Jennifer Lopez, Ricky Martin, Christina Aguilera, Enrique Iglesias, and Marc Anthony? And we can’t leave out the period’s biggest acts in Britney Spears, N-Sync, and Backstreet Boys. Or hip-hop legends like Jay-Z, Eminem, DMX, and Nas. Yes, some of these acts have either retired or, sadly, passed on, but many of them are still actively recording today. None of them reached the top 40 in 2025.
Excluding holiday recurrents, the last time an act from that era appeared in the top ten of the Hot 100 was in June 2024 when Eminem reached No. 2 with “Houdini,” his interpolation of Steve Miller Band’s “Abracadabra.” But “Houdini” was far from Shady’s greatest accomplishment and years from now fans won’t be holding it up as a late-career high watermark similar to the tunes by Santana, Aerosmith, Cher, and Sir Elton John.
Speaking of John, even he’s had more recent success than any of the acts who topped the Hot 100 in 2000-01. His “Cold Heart” (with Dua Lipa) and “Hold Me Closer” (with Britney Spears) both hit the top ten in 2022. That would also make Spears one of the more recent acts from the turn of the century to have success in the 2020s. But she hadn’t scored a top ten hit prior to that since 2012 (“Scream and Shout” with will.i.am), and it’s arguable that she wouldn’t have hit in 2022 if not for the nostalgia factor involving John and the momentum from his prior hit with Lipa.
So Why Are Artists from 2000-01 Failing to Chart Today?
The simplest explanation is likely the most uncomfortable: the artists didn’t disappear—the chart system that once sustained them did. What we’re seeing in 2025 isn’t a lack of relevance so much as a structural mismatch between how music used to become a hit and how it does now.
At the turn of the millennium, charts were driven by access. Radio, physical availability of product, and MTV exposure could introduce a song to millions of listeners and often trigger its growth. That’s how late-career smashes like Cher’s “Believe,” Santana’s Supernatural singles, and Aerosmith’s “I Don’t Want to Miss a Thing” slowly built momentum into massive hits. Today’s Hot 100, however, is powered by behavior and virility on social media. Streaming doesn’t reward familiarity or patience; it rewards immediate, repeated engagement, often driven by TikTok success. If a song by a veteran act can’t generate that kind of buzz, it disappears—regardless of the artist’s prior résumé.
Compounding that shift is the reality that nostalgia no longer works the way it used to. While catalog listening is arguably stronger than ever, based on the consistent performance of legendary albums by Fleetwood Mac, Queen, and Michael Jackson on the Billboard 200, that success is limited to those acts’ older material and not any new releases — if there are any. It also tends to be generation-specific, benefitting acts who long predate the turn of the millennium.
Streaming’s Impact
Today’s dominant streaming audience skews young, and their nostalgia touchstones are rooted in the 2010s—not the late 1990s or early 2000s. To many Gen Z listeners, artists like Matchbox 20, Creed, N*Sync, or even Britney Spears are cultural artifacts rather than active participants worthy of a massive comeback on the order of a Cher or a Santana. In the late ’90s, baby boomers and Gen X listeners still controlled radio and retail, creating a powerful lane for veteran artists. That demographic leverage no longer exists. Yes, the acts from that era may find success on the touring circuit, but that doesn’t translate into a major hit record on the charts.
Radio, once a crucial comeback engine, no longer fills that gap. It has become reactive rather than corrective, following streaming trends instead of shaping them. That shift has been especially punishing for adult-leaning pop, R&B, and Latin artists—Brian McKnight, Joe, Jagged Edge, Enrique Iglesias, Marc Anthony, Jennifer Lopez—who once thrived in a crossover lane that has all but disappeared, despite efforts to the contrary. The backlash that engulfed Lopez’ 2025 album was particularly intense. Jagged Edge’s recent comeback single (“Just Might Get It”) found top 20 success on the highly niched Adult R&B Airplay chart but crossover appeal now eludes that genre. Usher tried to ride Super Bowl halftime momentum to a pop chart hit in 2024, to no avail. The romantic mid-tempo songs that once bridged formats simply don’t fit today’s chart logic.
Older Acts Can’t Rely on Reinvention Alone
Reinvention, too, has become harder and less forgiving. It often requires an assist from timing or fate. Cher didn’t just transform in 1999, she also rode a wave of public sentiment in the wake of ex-hubby Bono’s death — and her impassioned eulogy — a few months before “Believe” was released. Santana didn’t rely on nostalgia, he collaborated with contemporary acts — first with then-red hot Rob Thomas of Matchbox 20 and later with the Product G&B and era favorite Michelle Branch.
Aerosmith, who’d been consistent hit makers for most of the ‘90s, had the benefit of a huge movie tie-in with Armageddon. Elton John was a chart staple whose personal connection with the beloved Princess Diana transformed a perfectly reframed 1973 favorite (“Candle in the Wind”) into an authentic tribute that resonated with millions following her tragic death.
But in 2025, reinvention requires not just musical evolution or a big event, but fluency in social media, platform culture, and viral mechanics. Many legacy artists either don’t want to play that game or find their success off the Hot 100, like Creed or Coldplay—because the singles charts of today offer no exemption for those who don’t play along.
Jay-Z Won’t Play; Beyoncé and Taylor Could Change Things
Even the biggest names aren’t immune. Jay-Z didn’t lose relevance; he’s apparently just lost interest in releasing new music. Perhaps he sees the writing on the wall and chooses to leave his No. 1 album legacy intact. Perhaps he knows what happened when period peers like Usher, Lopez, and Diddy attempted comebacks in recent years. Yes, those artists remain relevant in social media and news cycles, but pop radio and the younger TikTok generation steer clear of them.
The key difference between then and now is simple. Hits by legacy artists once combined nostalgia with exposure. Now they come from built-in followers and habit. Those habits will work for the long term success of special artists like Taylor Swift, Beyoncé and others from this era who weren’t charting (at least not solo in Bey’s case) in 2000 but started not too long afterwards. Taylor is enjoying her greatest success nearly 20 years into her chart career and Bey has promised the third installment of her Renaissance trilogy, which will likely coincide with her 25th year as a solo artist. Surely the two of them and a few others will be topping the charts more than 25 years into their careers.
Artists from the class of 2000 didn’t age out of relevance. They aged out of methodology. In another system—another era—many of them would still be charting. But the Hot 100 of 2025 isn’t a legacy scoreboard. It’s a real-time reflection of consumer behavior.
And for this generation of stars, the door wasn’t closed.
It was simply rebuilt somewhere else.
DJRob
DJRob (he/him) is a freelance music blogger from the East Coast who covers R&B, hip-hop, disco, pop, rock and country genres – plus lots of music news and current stuff! You can follow him on Bluesky at @djrobblog.bsky.social, X (formerly Twitter) at @djrobblog, on Facebook or on Meta’s Threads.
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