That Year That Killed Careers

Every artist will have their last big hit. However, one year stands clear as the end for more legends than any other. Why did this year kill so many careers? What can it teach us about 2024?

Matt Bailey

Sep 12, 2024

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It’s time to talk about death—of artists’ hit music careers, specifically.

The Beatles, Nirvana, Tupac Shakur and The Notorious B.I.G. are in their own league of legendary, in part, because they never got the time to become irrelevant. (Imagine a world where Bono, Eddie Veddder or Kanye West left us before they had time to… uh… mature.)

Thankfully, most artists do get that chance.

Even for those legendary performers who somehow always evolve with changing musical styles and cultural moods, there comes a time when they, too, can’t keep up with the times.

Is there any pattern to when our collective musical tastes finally turn on our heroes? Is there anything we can learn about when today’s artists’ careers might end?

Here’s the analysis I performed to answer these questions:

(If you’re a time-pressed radio programmer, feel free to scroll to the end to find out why Taylor Swift is safe but Dua Lipa isn't.)

How I analyzed artist career endings by year

I examined every Top 10 hit on the Billboard Hot 100 from its inception in 1958 through today.
Next, I drilled down to those artists who cumulatively spent more than half a year (26 weeks) in the Top 10, a group of 226 artists. (For context, REO Speedwagon, Milli Vanilli, Outkast, and Ellie Goulding barely made the cut. Carly Simon, Tears for Fears, Sheryl Crow, Lifehouse, and Fetty Wap just missed it.)
Finally, I ignored any artist whose most recent Top 10 has been in 2020-2024, since it’s too soon to determine if their last hit is really their last.

I then examined the years each artist had their last Top 10 hit and measured those years by four factors:

How many individual artists’ had their final Top 10 hit in each year? (I did not count remakes, rechartings, collaborations, or Christmas music.)
How many Top 10 hits had those artists totaled in their careers? Madonna’s 38 Top 10s are more consequential than The Real McCoy’s two.
How many cumulative weeks had those artists spent in the Top 10? Mariah Carey’s four and a half years (not even counting Christmas) is more consequential than The Bangles’ six months’ worth of Top 10.
How long was the average career lifespan from first to last Top 10 hit? Stevie Wonder and The Rolling Stones spent a quarter of a century making Top 10 hits. Air Supply only spent three.

Combining these four factors, I created the Career Killer Index (C.K.I.) score for each year to determine how big were the careers that each year killed. 100% is an “average” year.

When are artists’ careers most likely to end?

Only 13 years stand out as career-killing years, with one clearly outranking all others.

Was it 1979, when Disco backlash suddenly took anything remotely soulful off the charts? Nope. Chic, Gloria Gaynor, and The Village People ended their short-lived runs in 1979, but not artists who were big before Disco.
Was it 1964, when the Beatles spawned the British Invasion? Not even close.
What about 1992, when Grunge reported killed Hiar Metal? You’re getting warmer, but you’re off on which generation of artists left the charts.

But one year did mark the end of a massive roster of musical icons: The Year of Our Taylor’s Birth, 1989.

From 1988 to 1990, a slew of Oldies legends with hits dating back to the 1960s had their very last Top 10 hits. Some hadn’t been in the Top 10 for years, Others had never stopped making hits.

Why did the end of the 80s end so many hit-making careers? What were these icons’ last contemporary hits? And is there anything that the end of the 1980s can teach us about the mid-2020s?

Before we answer the “why’s”, let’s look at the who’s, along with the songs that ended their Top 10 hits.

Nine Icons whose Hits Ended in 1989

The artists fall roughly into three categories.

Category #1: Artists that made one last big comeback

These artists’ comebacks may have been short-lived, but their last top 10 hits have stood the test of time. You’re likely to hear them on your local Classic Hits station this week.

1) The Beach Boys

They personified America’s obsession with Southern California when "Surfin' U.S.A.", was #3 in 1963, kicking off a string of 13 Top 10 hits culminating in the masterpiece “Good Vibrations.” Then, their cultural cache tanked. They were done with surf music—it was woefully uncool anyway. But critics and contemporaries panned Brian Wilson’s attempts to create innovative music in the psychedelic era.

They continued making music. 1974’s "Sail On, Sailor" only reached #49 on the Hot 100, but became an album-rock sleeper. Not so remembered was 1987’s colab with The Fat Boys’ “Wipeout.” Other than a forgettable remake of Chuck Berry’s Rock ‘n’ Roll Music in 1976, however, none reach the Top 10.

Then Tom Cruise remade Top Gun as a bartender with a blender. Thanks to Cocktail, The Beach Boys had their first #1 hit in 22 years in November 1988 with "Kokomo.” The comeback wouldn’t last. “Kokomo” accounted for the last of the Beach Boys’ 71 weeks in the Top 10.

2) Roy Orbison

You might not realize just how big he was in his day. From his debut Top 10 “Only The Lonely” in 1960 to 1964’s #1 “Oh, Pretty Woman,” Roy Orbison had nine songs spend 41 weeks total in the Top 10. He kept recording, but other than an Emmylou Harris duet on the Country charts, his hits were over.

Then in 1988, an unlikely Rock supergroup The Traveling Wilburys returned Orbison to the spotlight. The following year—our fabled 1989— “You Got It” returned Orbison to the Top 10 for one final week.

Sadly, Orbison didn’t get to enjoy it. Exhausted from his newly busy touring schedule, he died of a heart attack in 1988 at age 52.

3) George Harrison

Speaking of The Traveling Wilburys, they would also revive Harrison’s career. On his own, he had Top 10 hits with “My Sweet Lord” and “Give Me Love.” Other than his 1981 tribute to John Lennon (“All Those Years Ago”), however, Harrison hadn’t been in the Top 10 since 1973. (1979’s “Blow Away” should have been, imho.)

Then in early 1988, Harrison hit #1 with his last Top 10 hit, “"Got My Mind Set on You". Alternatively sung, “This Song’s Just Six Words Long,” tacked on another eight weeks in the top 10, totaling 32 weeks as a solo artist and 204 weeks in the Top 10 as a Beatle. He’d release four more singles in his lifetime, including the minor Beatles retrospective “When We Was Fab,” before his 2001 death.

1988’s “Got My Mind Set On You” marks the last contemporary Top 10 hit for any solo Beatles member.

Sidenote: Not counting his 2015 collaboration with Rihanna and Kanye West, when was Paul McCartney’s last Top 10 hit?

As a Beatle in the 1960s, front man for Wings in the 1970s, and popular duet partner in the early 1980s, McCartney had 54 hits totaling over six years’ time in the Top 10, the most of any Beatle. And his last Top 10 solo hit?

A forgettable song from an even more forgettable film, 1986’s “Spies Like Us.”

Category #2: Artists who tried one last comeback

These artists also had one last hit, but their comebacks have been largely left in the past.

4) Donny Osmond

Jessica Ettinger, Music Director of New York’s 95.5 WPLJ, had discovered a great song in the U.K. She knew would be a hit. Only problem? The artist was so woefully uncool, her listeners would dismiss it outright if they knew who sang it.

So, Ettinger created a “mystery artist” promotion around the song. Only after her listeners were clamoring for “Solder Of Love” did listeners learn—live on air from the man himself—that they’d been tricked into liking the new song from Donny Osmond.

It’s easy to forget how big the Mormon Michael Jackson was in the early 1970s. Between his family group, duets with his sister Marie, and his solos, Donny Osmond had 11 hits totaling over a year in the Top 10 from 1971 to 1975.

It’s also easy to forget how NOT Michael Jackson Osmond was. "I'm Leaving It Up to You,” Donny & Marie’s remake of the Dale and Grace, is tellingly the absolute most “lost” song of the 1970s, according to radio consultant and music guru Sean Ross. By Ross’ meticulous calculations, it’s the biggest hit of the decade that virtually nobody plays anymore.

Donny Osmond’s comeback wouldn’t last. “Solder of Love” was his last Top 10 hit. (The follow-up, “Sacred Emotion”, was a hit on Adult Contemporary radio.)

Unlike “Kokomo” or “You Got It”, you likely won’t hear Soldier on today’s Classic Hits stations.

5) The Bee Gees

Unless you’re a fellow Oldies fanatic—or over 60—you may have no clue about The Bee Gee’s Debbie Downer phase. In 1968, “I've Gotta Get a Message to You," a tale of a death row inmate, became their first Top 10 hit in the U.S.. It kicked off a string of feel-good favorites about fake mining disasters, broken hearts, lonely days, and causing the whole world to cry.

How unlikely it was, then, that in 1975, the Bee Gees reinvented themselves as Disco kings, with ten Top 10 bangers during rest of the 1970s and racking up almost two years total in the Top 10.

After the Disco backlash, the Bee Gees still wrote hits, from Dionne Warwick’s Adult Contemporary classic “Heartbreaker,” to Kenny and Dolly’s “Islands In The Stream.” But no one wanted to hear them from the Bee Gees.

With Disco backlash faded, The Bee Gees released "One.” It was an appropriately titled comeback. It was Top 10 for exactly one week, peaking at #7 in 1989.

6) The Doobie Brothers

There are two Doobie eras. Swamp Rock featured Tom Johnston on lead vocals and included 1973’s "Long Train Runnin,” and “Black Water” in 1975. Yacht Rock begins with Michael McDonald, culminating in “"What a Fool Believes,” the song that invented that Doobie Bounce.

We Gen Xers—whose wistful childhood nostalgia has made the retroactively named Yacht Rock genre cool—will deny it, but there was absolutely nothing cool about those smooth late 70s classics in 1989.

What was big in 1989? Boomer nostalgia.

Therefore, it was the Swamp Rock Doobies who attempted a comeback in 1989, with Tom Johnson singing how music is “The Doctor” of his soul. It was only top 10 for a week and you probably haven’t thought about it since the fall of the Berlin Wall.

Category #3: Artists whose hits finally dried up

These hit-makers both never went away and continued evolving through music’s trends. However, their relevance finally faded alongside the Reagan Administration.

7) The Rolling Stones

What would have happened had the Beatles never broken up?

Many ponder this question wistfully, imagining a world where the Fab Four remained alive and together for decades. We assume they’d make music as meaningful to folks in the late 1980s as they still did in the late 1960s.

We ignore a more likely scenario---they could have gone out like The Rolling Stones.

Their first U.S. Top 10, 1964’s “"Time Is on My Side", reflected their roots as fans of the blues music America seemingly forgot. From 1965’s "(I Can't Get No) Satisfaction" to 1969’s "Honky Tonk Women," their 10 Top 10 hits define the sound of the Sixties.

Pivoting to Album Rock in the 1970s and dabbling with Disco (“"Miss You" was their last U.S. #1), the Stones kept having hits throughout the 1980s. The last of their Top 10 hits, however, is no, “The Long and Winding Road." It’s not even “Miss You.”

"Mixed Emotions" reached #5 in October 1989, on the excitement of the Stones’ new Steel Wheels album and tour.

Don’t remember it? You’re not alone.

35 years after their hits faded, The Rolling Stones are still releasing new material in 2024. Their 2020 track “"Living in a Ghost Town" was both timely and highly praised by critics who took time to play it.

8) Chicago

There was a time when Chicago was actually a Rock band. Starting with "Make Me Smile" in 1970, their first half-dozen Top 10s in the early 70s were comparable to their contemporaries “Blood, Sweat & Tears,” “The Ides of March,” or ”The Grass Roots.” While those bands’ chart runs didn’t survive the original network run of The Brady Bunch, Chicago—or more accurately their record label—stumbled on two changes. 1) Make Peter Cetera the main vocalist and 2) sing sappy love songs.

They could sing 70s-style sappy ballads, such as “If You Leave Me Now" (#1 and Top 10 for 9 weeks).

They evolved to sing 80s-style sappy ballads, starting with "Hard to Say I'm Sorry" (#1 and Top 10 for 12 weeks).

Ultimately, while they spent 38 weeks in the Top 10 with actual Rock in the 70s, they spent 60 weeks in the Top 10 with their ballad years.

By the late 80s, Chicago and Peter Cetera had split. Their signature horn section was missing, such as on their last #1 in 1988, “Look Away” When "What Kind of Man Would I Be?" became their last Top 10 hit in February 1990, the only thing Chicago about the group was that logo.

9) Don Henley

Technically not contributing to 1989’s colossal Career Killing Index (CKI) above, as his four solo Top 10s only totaled 18 weeks, Don Henley is to the Eagles as George Harrison is to the Beatles—the last hit-making member of a legendary group. (Glen Frey’s two saxophone-laden solo Top 10s both came in 1985). As an Eagle, Henley spent 60 weeks in the Top 10, plus eight weeks with his #1 duet with Stevie Knicks “"Leather and Lace."

True to how we Gen Xers think of Boomers, Henley’s last Top 10 hit was the melancholy, politically tinged harangue “End Of The Innocence,” wherein he somehow uses the bleakness caused by everyone from divorce attorneys to Ronald Reagan to convince some women to have sex with him in some field.

Despite promising otherwise, the Eagles got back together in 1994. The reunited band’s only new single from their live performance album Hell Freezes Over, the hypocritically judgmental Boomer rant. “Get Over It.” Xers weren’t having it. The song stalled at #31 on the Hot 100.

Know a chart geek or Oldies fan who would enjoy this post?

Why Did 1989 Kill So Many Careers?

Name the Hot 100 artist who had more Top 10s than The Beatles, Elvis Presley, Michael Jackson, Madonna, Rhianna, or Drake and who is not Taylor Swift?

From 1945 to 1958, pre-Rock crooner Perry Como had 46 of them. None counted towards this analysis, since they were all before the Hot 100 launched in 1958. In the early 1970s, though, Como came back with two final mainstream hits; "It's Impossible" and the Chris Christopherson penned, “and I Love You So.”

So did crooner Andy Williams, who enjoyed his last Top 10 in the early 1970s with the movie theme, "(Where Do I Begin?) Love Story."

They marked the end of the chart hits for the jazz-based Pop standards that dominated hit music before Rock ‘n’ Roll.

Fast forward to 2009. Guitar-based Rock ended five decades of Top 10 hits when Shinedown’s “Second Chance” unceremoniously became the last contiguous Top 10 Rock hit, (as I showcased in Rock is Dead. Long Live Rock..)

Why—or better asked when—do entire genres have one last hurrah before disappearing from the charts?

It happens right before a new generation becomes the dominant hit-makers and introduces a new genre to the mainstream.

As I detailed in The Generational Music Theorem, these periods in popular music when a new generation becomes the primary hit-making artists are revolutionary periods on popular music. They are times when mainstream music tastes change suddenly, often confusing even music industry captains.

Those last Crooner hits happened just before the Boomers overtook the Silent generation as the hit-makers and ushered in what we now call “Classic Rock”, from The Eagles and The Doobie Brothers to Pink Floyd and Led Zeppelin.
Likewise, Rock left the charts just as Millennial artists made EDM (Electronic Dance Music) mainstream around 2010. (Read about Rock’s death here.)

Generation of the hit-making artists of Top 10 hits in a typical week. For groups, generation calculated by averaging birthrate of the group’s most significant members. Generations defined by birth cohorts defined in “Generations” by William Strauss and Neil Howe.

1988-1990 coincides with the time just before Generation X overtook Boomers as the primary hit-making artists.

When they did, they morphed Rock into Grunge and made Hip Hop mainstream. (I wrote about how Hip Hop overthrew Rock here.)

The tension created in this generational transfer of hit-making power during a revolution creates a short window for one last round of the older generations’ style of music. In 1989, that meant modern “Oldies,” from “Kokomo” and “You Got it” to Rod Stewart’s “The Motown Song,” (with help from the actual Temptations) to Michael Bolton butchering a 1960s R&B classic.

If this pattern is both cyclical and predictable, why did more careers end around 1989 than, say, the late 2000s or the early 1970s?

There were longstanding career deaths during that time.

In addition to crooners, the mid 1970s saw brief but short-lived comebacks for 1950s Teen Idols Neal Sedaka and Paul Anka.
Madonna and Mariah Carey scored their last contemporary Top 10s as the 2000s ended.

However, the 1960s Oldies icons whose last hits came in the late 80s became hit-makers before Pop, Rock and R&B splintered into separate listener bases in the 1970s. It’s a lot easier to have a large fan base and a ton of Top 10 hits when you don’t have to cross over to do it. Back then, it was all Rock ‘n’ Roll.

Plus, let’s be honest here. When the Boomers decided to become nostalgic, they sure as sin were going to make sure the rest of us had to hear about it. Gen Xers can only do nostalgia ironically.

What does 1989 teach us about 2024?

As I wrote in The Generational Music Theorem, we are on the cusp of—or perhaps already in the beginning of—an evolution in popular music. For the next decade, Millennials (born before 2005, according to the historian who invented the label) will continue to perform the hits. However, Generation Z is taking control of which songs become hits.

Our current point on the Generational Music Cycle is comparable to 1982 (I covered that comparison here), when Boomers like Michael Jackson and Madonna made the music, but Generation Xers determined the hits. Gen X also embraced MTV-style New Wave, starting an evolution of popular music that made new music fun again and revived Top 40 radio.

Similar evolutionary periods in the Generational Music Theorem include

The 1964 British Invasion when Boomers spawned Beatlemania, but Silent Generation artists like Simon and Garfunkel still made the hits, and
Crunk ‘n’ B in 2003, when Millennials took away Hip Hop’s Gen X grit and made it party music.

The artists whose careers typically end before a music evolution aren’t the icons whose last hits come before a revolution. More typically, they’re stars who have a lot of hits in a short time with a style that appealed to the older generation.

In 1983, as the New Wave evolution revived pop music, the biggest artist to see the hits end was Air Supply, whose eight sappy hits spent over a year in the Top 10 during their three-year chart run. Rick Springfield, Christopher Cross, and Toto would also end their bright but brief careers during this time frame.
In 1963, just before Beatlemania, it was Brenda Lee (the real Queen of Christmas) whose three-year chart run of 12 Top 10 hits ended. The year before, Connie Francis’ even bigger string of hits ended after only three years.
In the early 2000s, 3 Doors Down, Matchbox Twenty, and Creed typified the artists whose short chart runs ended.

Whose Careers Will Die in 2024?

The careers we can expect to end soon are artists who 1) only began their chart run within the past few years and 2) make music more to the tastes of Millennials than to Generation Z.

It’s a lot more likely Dua Lipa, Lizzo, or Doja Cat are on borrowed time than Taylor Swift or Drake (despite Kendrick Lamar’s efforts), whose careers already span 15 years.

Olivia Rodrigo, Lil Nas X, and Billie Eilish may be safer, as they appeal to younger fans, but they too could be vulnerable to short careers if emerging artists quickly surpass their appeal among Generation Z.

Advice for radio programmers in 2024:

Be mindful of big stars from recent years who suddenly become irrelevant. CHR stations were quick to add Dua Lipa’s “Illusion,” even though the song dramatically under performs on streaming, (as I’ve noted in The Hit Momentum Report for programmers.)
Don’t write off the icons yet. It may become tempting in the next year or so to assume Drake, Beyonce, Miley Cyrus, or Rihanna have grown too old to still be relevant to today’s hit music fans. However, these performers have already proven their ability to evolve with time and taste. There’s no guarantee any of these artists individually have more hits ahead. History strongly suggests, however, that listeners will remain open to any relevant songs they create for at least the remainder of the 2020s.
Expect Millennials’ nostalgia to keep growing this decade. We’re already seeing older Millennials’ newfound interest in the music of the Boy Bands of the late 1990s and the Crunk Hip Hop of the early 2000s. That trend will likely intensify in coming years and ultimately expand to the EDM infused years of the 2010s.

So when can we expect another wave of iconic careers to end? If 2024 is the new 1982, then expect the next 1989 to be around 2031.

Uhm… What about 2001?

The astute among you is noting, “so what’s with that spike in 2001, Matt?”

It’s stems chiefly from just three artists who had their last hits that year—-but they weren’t mere mortal music makers:

Janet Jackson had her last of 28 Top 10 with "Someone to Call My Lover", the follow up to her #1 "All for You"
Whitney Houston had her last of 23 Top 10s before her tragic death when “The Star Spangled Banner” became a patriotic comfort after 9/11. It’s the only Top 10 rendering of our national anthem.
Michael Jackson’s 28-song Top 10 chart run in his lifetime (not even including the 11 hits with his siblings) ended unceremoniously with "You Rock My World" spending one week at #10.

These three artists alone spent over 11 years combined in the Hot 100’s Top 10. That’s more than twice the total weeks in the Top 10 for the three biggest artists whose careers ended in 1989.

For the remaining years with above-average Career Killer Indecies, here are the biggest artists that had their last hits during that year.

1974: The Temptations, The Four Tops, and Three Dog Night
1980: The Eagles, Captain & Tennille, and KC & the Sunshine Band
1985: Aretha Franklin, Diana Ross, and Dionne Warwick
1993: Rod Stewart, Billy Joel, and Duran Duran
1994: Prince, Bon Jovi, and Richard Marx
1996: Barbara Streisand, George Michael, and Eric Clapton
2008: Madonna, Christina Aguiler, and Nickelback
2011: The Black Eyed Peas, Jennifer Lopez, and Britney Spears
2016: Flo Rida, Pink, and Kelly Clarkson