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PHOTO BY: Axel Heimken/picture alliance via Getty Images
October 2: Sting, 70
After bursting on the scene with the Police, Sting has proven to be an musical chameleon: collaborating on an Elizabethan-inspired album with a Bosnian lutist and a reggae album with Jamaican musician Shaggy, writing a Broadway musical (The Last Ship) about shipbuilding, and introducing Western audiences to Algerian folk music with “Desert Rose.” Despite earning a Kennedy Center Honor and winning 17 Grammys, an Emmy and a Golden Globe, the British star has never lost his cheeky sense of humor. Case in point: He’s currently starring as himself in the Hulu crime comedy Only Murders in the Building.
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PHOTO BY: Harmony Gerber/Getty Images
October 2: Tiffany, 50
The 1980s teen icon performed her pop songs at shopping malls — perfect exposure for promoting her second single and biggest hit, a cover of Tommy James & the Shondells’ “I Think We’re Alone Now.” Among her later projects: appearing in a Miracle Whip commercial and on Celebrity Wife Swap, and acting in a few films, including a horror flick called Necrosis.
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PHOTO BY: Gabe Ginsberg/Getty Images
October 3: Chubby Checker, 80
No singer got Americans moving more in the 1960s than this South Carolina–born rock pioneer. His hits, such as “The Twist,” “Pony Time,” “Let’s Twist Again” and “Limbo Rock,” spawned dance crazes that fuel weddings and bar mitzvahs to this day. When the Rock & Roll Hall of Fame introduced a new singles category in 2018, “The Twist” was among the first class of inductees. Checker himself shockingly still hasn’t made the cut as an artist, which led him to publicly protest the snub outside the 2002 induction ceremony.
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PHOTO BY: Desiree Navarro/Getty Images
October 4: Jon Secada, 60
The Havana-born crooner got his musical start as a backup singer for the Miami Sound Machine (he co-wrote Gloria Estefan’s “Coming Out of the Dark”), and he has released songs in both Spanish and English, including popular singles like “If You Go” and “Just Another Day.” He later brought his considerable charisma to Broadway, where he starred as Danny Zuko in Grease and the Emcee in Cabaret, and he helped crown the next generation of pop stars as a judge on Latin American Idol. His last album, 2017’s To Beny Moré With Love, was a tribute to the late Cuban bandleader, and it won the Latin Grammy for best traditional tropical album.
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PHOTO BY: Mark Sagliocco/Getty Images
October 7: John Mellencamp, 70
The Hoosier State hitmaker — who officially dropped the “Cougar” stage name 30 years ago — has earned commercial and critical acclaim for his plainspoken anthems about small-town, working-class Americans, such as “Jack & Diane” and “Pink Houses.” When it comes to heartland issues, the Rock & Roll Hall of Famer and Grammy winner put his money where his mouth is: Farm Aid, which he cofounded in 1985, has raised more than $60 million for American farmers. This August, Mellencamp released a live album, The Good Samaritan Tour 2000, and an accompanying documentary, which is available to stream on the Turner Classic Movies YouTube channel.
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PHOTO BY: Evan Agostini/Invision/AP
October 13: Paul Simon, 80
When the Library of Congress debuted the Gershwin Prize for Popular Music in 2007, the Newark native was a shoo-in to be its first honoree. Alongside Art Garfunkel and later as an acclaimed solo artist, Simon has reshaped the American songbook with poetry-rich classics like “Bridge Over Troubled Water” and “You Can Call Me Al.” In 2001, he became the first artist in Grammy history to be nominated for album of the year in five consecutive decades — an award he’s won three times. He released his 14th solo studio album, In the Blue Light, in 2018 and was set to perform in Central Park this August at the We Love NYC: The Homecoming Concert until a severe storm shut it down.
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PHOTO BY: Rick Rycroft-Pool/Getty Images
October 13: Sacha Baron Cohen, 50
This actor is English, but most recent movie watchers likely have never heard his refined British accent. He replayed his (fake) Kazakhstani schtick as Borat Sagdiyev, a news reporter baffled by America, in last year’s Borat Subsequent Moviefilm, the sequel to his 2006 mockumentary also starring the hapless Borat. And he offered a convincing, dry-humored performance as an American, Yippie protestor Abbie Hoffman, in The Trial of the Chicago 7.
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PHOTO BY: Erika Goldring/Getty Images
October 18: Wynton Marsalis, 60
Born in New Orleans to a family of jazz greats, Marsalis seems to have music in his bones, and he’s become one of the most celebrated trumpeters alive today. The artistic director of Jazz at Lincoln Center, he’s racked up nine Grammys, and his Blood on the Fields oratorio was the first jazz composition to win the Pulitzer Prize for Music. During the COVID-19 lockdown, he and the Jazz at Lincoln Center Orchestra Septet recorded The Democracy! Suite, an inspirational jazz album about the democratic process and the fight for social justice.
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PHOTO BY: Paras Griffin/Getty Images for 2016 Essence Festival
October 18: Terry McMillan, 70
When the Michigan-born author started publishing her crowd-pleasing novels in the 1980s, she was scratching an itch the literary world didn’t even know it had, offering an honest and aspirational look at the lives of contemporary Black women. Her bestsellers have sold 15 million copies and spawned two hit Hollywood adaptations, Waiting to Exhale and How Stella Got Her Groove Back. She released her 12th novel, It’s Not All Downhill From Here, about a 68-year-old beauty entrepreneur and her friends, last year.
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PHOTO BY: Prince Williams/FilmMagic
October 20: Snoop Dogg, 50
Now a multiple-threat entertainment juggernaut, Snoop Dogg first made it big in 1993 with his Dr. Dre–produced hit record Doggystyle. At various points since then he’s — among many other things — embraced reggae and gospel, been a mega mentor on The Voice, and become pals and business partners with Martha Stewart (together they headline the VH1 series Martha & Snoop's Potluck Dinner Party). His advice about getting older? “You got to treat yourself like fine wine,” he told People. “They say fine wine, it gets better over time.” He’s actually released two wines under his name since last year — Snoop Cali Red and Snoop Cali Rosé — through the brand 19 Crimes.
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PHOTO BY: Billie Weiss/Boston Red Sox/Getty Images
October 25: Pedro Martínez, 50
A three-time Cy Young Award winner and eight-time All-Star, this Dominican American powerhouse was one of the most unhittable pitchers in Major League history — despite his small stature, which earned him the nickname “Petey.” Martínez played for five teams across his 18 seasons, most notably the Boston Red Sox (1998-2004), whom he helped win their first World Series in 86 years. After retiring in 2009, he was inducted into the Baseball Hall of Fame in 2015 in his first year of eligibility, and he now focuses his attention on the Pedro Martínez Foundation, dedicated to helping at-risk youth in the Dominican Republic and beyond.
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PHOTO BY: Jeff Kravitz/FilmMagic
October 29: Winona Ryder, 50
Sure the Brat Packers were considered the It crowd of ’80s film, but Winona is Gen X’s top dog — starring in iconic flicks like Reality Bites, Heathers and Edward Scissorhands. Last year she appeared in HBO’s drama The Plot Against America, but her highest-profile project in decades has been her role as mom Joyce Byers in Netflix’s hit horror series Stranger Things, whose fourth season is in the works. How has she coped with this latest surge of media attention? “I’m not on the internet that much,” she told Jimmy Kimmel, “but my parents are, and they forward me the good stuff.”
Nicholas DeRenzo is a contributing writer who covers entertainment and travel. Previously he was executive editor of United Airlines’ Hemispheres magazine and his work has appeared in the New York Times, Conde Nast Traveler, Travel & Leisure, Sunset and New York magazine.
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