Time deals harsh blows to even our greatest musical heroes. Twenty legends now approach 90, carrying the weight of past traumas alongside their achievements. Many battled addiction while creating timeless songs we still cherish. Others lost children, partners, and even their ability to perform the very art that defined them.
20. Ringo Starr
Growing up on Liverpool’s mean streets prepared Ringo for Beatlemania’s wild ride. Childhood illness kept him hospital-bound for years, developing patience that later defined his steady drumming. With the Beatles, his distinctive backbeat anchored over 200 tracks while the others grabbed headlines. After the breakup, he scored five consecutive top 10 hits before alcohol problems threatened everything. His daughter’s 1995 brain tumor diagnosis became his wake-up call. Ringo got sober, recommitted to family, and kept his All-Starr Band tours rolling. That 2018 knighthood completed his journey from sickly Liverpool kid to Sir Richard Starkey—proof that sometimes the steady drummer finishes first.
19. Tom Jones
TB nearly killed Tom Jones before his voice conquered the world. Bedridden for two years as a kid, he somehow developed vocal cords of steel. Marrying Linda at 16 gave him stability while “It’s Not Unusual” launched his stratospheric rise. Success unleashed temptations—Jones never hid his notorious backstage encounters despite his marriage. His powerful voice brought a TV series and 36 UK Top 40 hits spanning decades. Linda’s 2016 death after 59 years together devastated the usually tough performer. At 84, that thundering baritone still electrifies audiences worldwide—carrying emotional depth absent in his early recordings.
18. Judy Collins
Behind Judy Collins‘ crystalline soprano lurked personal demons few fans suspected. Her “Both Sides Now” interpretation earned a Grammy in ’68 while she secretly battled severe bulimia and alcoholism. When her son Clark died by suicide in ’92 at just 33, Collins channeled devastating grief into mental health advocacy. Her memoir “Sanity and Grace” documented her healing journey without sugar-coating the pain. Miraculously, her voice remains pristine at 85, allowing continued touring where every note resonates with hard-won wisdom and survival.
17. Grace Slick
Counterculture found its queen when Grace Slick brought her operatic power to Jefferson Airplane in ’66. Her commanding vocals turned “Somebody to Love” and “White Rabbit” into revolution anthems. Performing at Woodstock and Altamont placed her at ground zero for rock’s defining moments. Substance abuse derailed her in the late 70s, culminating in a drunken Nazi-referencing German concert that ended her Starship tenure. Despite personal chaos, she helped Jefferson Airplane secure their Rock Hall induction in ’96. Today her trippy canvases fetch thousands at galleries—a second creative chapter proving that artistic reinvention beats retirement any day.
16. Tommy Sands
Capitol Records struck gold when Tommy Sands‘ “Teenage Crush” rocketed to number 2 in ’57. His wholesome image made him the Elvis alternative parents preferred during rock’s rebellious early days. Marrying Nancy Sinatra briefly boosted his profile through Frank’s considerable industry clout. Their divorce coincided with British Invasion bands making his style suddenly obsolete. Despite 14 albums and several film roles, lasting success eluded him professionally and personally. Sands’ trajectory from magazine covers to obscurity serves as the textbook case of how rapidly changing musical tastes can leave yesterday’s sensation wondering what happened.
15. Shirley Bassey
From Cardiff’s rough Tiger Bay neighborhood emerged Shirley Bassey‘s indomitable spirit and hurricane-force vocals. “As Long as He Needs Me” showcased the powerful instrument that would become her trademark. Family crisis hit early—her father’s imprisonment forced teenage Shirley to become a breadwinner. Hard work yielded 70+ albums and 35 million records sold worldwide. Those Bond themes—”Goldfinger,” “Diamonds Are Forever,” and “Moonraker”—showcased her dramatic range perfectly. Her daughter Samantha’s mysterious 1985 death shattered her world completely. Still performing at 87, each Bassey note represents triumph over poverty, racism, and personal heartbreak.
14. Buddy Guy
Louisiana sharecropper’s son Buddy Guy transformed Chicago blues with his emotional intensity and groundbreaking techniques. Early years found him backing legends at Chess Records while developing his distinctive style. His club Legends became Chicago’s blues mecca after opening in 1989. When most guitarists fade away, Guy experienced an astounding renaissance, winning eight Grammys after turning 60. His playing still swings from whisper-quiet to explosive, keeping audiences perpetually on edge. Watch Guy perform at 88 and you’re witnessing living history—the last direct connection to blues’ golden era still pushing boundaries instead of playing it safe.
13. Kris Kristofferson
Tossing aside his Rhodes scholarship and Army captain bars, Kristofferson gambled everything on Nashville songwriting dreams. His “Sunday Morning Coming Down” perfectly captured hangover angst with literary precision when country music played it safe. Industry rejection continued until Johnny Cash’s version won Song of the Year at the 1970 CMAs. Between failures, he swept Columbia Studios floors just to stay near music. Classics like “Help Me Make It Through the Night” found homes with 450+ artists. Later career memory issues sparked Alzheimer’s fears until doctors discovered treatable Lyme disease instead. His intellectual risk-taking elevated country songwriting from simple stories to poetic art form.
12. Engelbert Humperdinck
Few career gambles paid off better than Arnold Dorsey’s transformation into romantic balladeer Engelbert Humperdinck. His 1967 “Release Me” famously blocked the Beatles from their 12th straight #1 in the UK—no small feat during Beatlemania. Across decades, that unmistakable voice sold 140+ million records while maintaining his signature style. Meanwhile, his marriage to Patricia endured 56 years until her 2021 death following Alzheimer’s and COVID complications. His performances now carry added emotional weight as audiences witness a man singing love songs after losing his greatest love—demonstrating music’s unique power to transform grief into connection.
11. Bill Wyman
Holding down the bottom end for the Stones from ’62 to ’93, Bill Wyman provided the rhythmic foundation that freed their wilder elements. His understated bass work on classics like “Paint It Black” created perfect space for Jagger’s swagger. Personal controversy exploded when he began dating teenager Mandy Smith, eventually marrying her when she turned 18—he was 52. Beyond the Stones, Wyman explored archaeology and photography while leading his Rhythm Kings band. His approach prioritized serving the song over flashy technique, anchoring the band’s sound through their most creative period. Wyman’s complex legacy spotlights how we struggle separating artistic contributions from problematic personal choices.
10. Johnny Mathis
Velvet-voiced Johnny Mathis pioneered the “make-out music” genre that soundtracked countless romantic evenings. Hits like “Chances Are” and “Wonderful! Wonderful!” established his career trajectory in 1957. While projecting romantic perfection, addiction demons threatened everything until sobriety in the early 80s brought creative renewal. His astonishing 73 studio albums have sold 350+ million copies worldwide—numbers that humble today’s streaming stars. The Guinness Book recognized his “Greatest Hits” album for an unprecedented 490-week Billboard chart run. In an industry obsessed with disposable trends, Mathis created timeless intimacy that technology can’t replicate.
09. Julie Andrews
Performing since age 10 to help feed her family, Julie Andrews turned necessity into virtuosity. Her perfect pitch and diction won her Broadway’s coveted Eliza Doolittle role at just 21. Personal challenges shadowed professional triumphs—her first marriage buckled under career pressures. The transition from stage to screen brought an Oscar for “Mary Poppins” before cruel irony struck in 1997 when throat surgery permanently destroyed her singing voice. Andrews pivoted to directing and children’s literature, publishing 30+ books with her daughter. Her reinvention demonstrates that creativity finds new channels when original paths disappear—an inspiring second act after losing her defining gift.
08. Doug Kershaw
Known as the “Ragin’ Cajun,” Doug Kershaw brought bayou sounds to mainstream audiences with fiddle pyrotechnics. Speaking only French until age 8 made him a cultural outsider in his own country. His father’s suicide when Doug was just 7 shaped both his emotional life and eventual music. “Louisiana Man” made history as the first song broadcast from space during Apollo 12’s mission. Speed and alcohol nearly derailed everything in the 70s before recovery extended his career decades longer. Unlike classical violinists, Kershaw holds his fiddle against his chest for that distinctive Cajun attack. His cultural ambassadorship ensured authentic Cajun music survived in an industry eager to dilute regional sounds.
07. Frankie Valli
That stratospheric falsetto propelled Frankie Valli and the Four Seasons to 175+ million records sold since their 1962 breakthrough. His voice—instantly recognizable within seconds—helped rack up 40 Billboard Hot 100 hits while maintaining remarkable consistency. Beneath the matching suits and perfect harmonies, personal tragedy struck when his daughter Francine died from a drug overdose in 1980. The Broadway musical “Jersey Boys” introduced his catalog to new generations while documenting the group’s complex history. Defying vocal aging, Valli still tours at 90 with new Four Seasons members—preserving an authentic American sound that remains impossible to duplicate.
06. Quincy Jones
From Great Depression poverty to music’s ultimate renaissance man, Quincy Jones defied every industry limitation. A teenage breaking-and-entering incident introduced him to the piano that changed his trajectory forever. Later surviving a near-fatal 1974 brain aneurysm requiring multiple surgeries, Jones refused to slow down. His production on Michael Jackson’s “Thriller” yielded 70+ million sales—still history’s biggest-selling album. With 28 Grammys from 80 nominations, his versatility spans genres most producers never attempt. After kicking early heroin habits, Jones worked across seven decades with artists from Sinatra to Kendrick Lamar. His career blueprint teaches a valuable lesson: mastering multiple lanes ensures relevance long after one-trick producers fade away.
05. Willie Nelson
The IRS came hunting Willie Nelson with a $32 million tax bill in 1990, forcing him to release “The IRS Tapes” album just to chip away at his debt. His distinctive behind-the-beat vocal phrasing creates tension no imitator has successfully duplicated. Willie’s battered guitar “Trigger” has been his companion for 50+ years despite having a massive hole worn through its body. Personal tragedy struck when his son Billy committed suicide in 1991—grief that permeated his subsequent work. His Farm Aid concerts have generated $64+ million for struggling family farmers. Still touring relentlessly at 91, Nelson remains the gold standard for artistic integrity in an industry where selling out is practically expected.
04. Petula Clark
Breaking barriers few female artists attempted, Petula Clark achieved global domination when “Downtown” topped charts in the US, UK, France, Australia, Germany, and Canada. While American stars stayed monolingual, Clark recorded in five languages, conquering multiple European markets simultaneously. Balancing international stardom with raising three children tested her limits repeatedly. Behind her cheerful public image, perfectionism and depression complicated her personal happiness. Her accidentally groundbreaking 1968 TV moment touching Harry Belafonte’s arm created the first interracial contact on American television—sending sponsors into hysterics while making quiet civil rights history.
03. Yoko Ono
Years before meeting John Lennon, Yoko Ono established herself as a boundary-pushing conceptual artist in New York’s avant-garde scene. Her 1964 “Cut Piece” invited audiences to slice away her clothing—exploring vulnerability decades before such performance art became common. After Lennon’s 1980 murder, vicious public hatred compounded her devastating grief. Depression, suicidal thoughts, and heroin dependency threatened to consume her during this dark period. Against all odds, Ono continued creating challenging work instead of retreating from view. Her album “Season of Glass” confronted loss directly with John’s bloodstained glasses on the cover. For 60+ years, her radical artistic vision has influenced creators across disciplines—whether they acknowledge her pioneering role or not.
02. Kenny Burrell
Jazz guitar elegance found its master in Kenny Burrell‘s sophisticated blues-inflected playing. His 1963 “Midnight Blue” album remains essential in the Blue Note catalog, defining cool jazz-blues fusion. Financial catastrophe struck in 2016 when medical bills created crushing debt that threatened to leave the jazz legend homeless. Fans mobilized through GoFundMe, raising $200,000+ to prevent this national disgrace. Throughout his career, Burrell contributed to 100+ albums alongside giants from Coltrane to Holiday. His UCLA teaching established one of America’s first serious jazz guitar programs in 1978. When Duke Ellington calls you his “favorite guitarist,” you’ve reached jazz immortality—even if healthcare costs nearly took your home.
01. Dick Van Dyke
Overcoming paralzying shyness, Dick Van Dyke developed physical comedy skills that defined television humor for generations. His pioneering sitcom ran five seasons, collecting 15 Emmys while revolutionizing TV comedy. Beneath his wholesome image, alcohol problems threatened both health and career throughout the 60s and 70s. His 36-year marriage ended in 1984, adding personal complications to professional challenges. Dance numbers in “Mary Poppins” showcased balletic precision disguised as effortless goofiness—far harder than it appears. Remarkably, at 99, Van Dyke still performs occasionally, including a desk-dancing sequence in “Mary Poppins Returns” without stunt doubles or effects—demolishing assumptions about creativity’s supposed expiration date.
