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Bob Dylan
Born
Bob Dylan was the acoustic voice of the folk revival when he played an electric set with a rock band at the Newport Folk Festival in 1965 and was booed by part of the crowd. He kept going, with Highway 61 Revisited and Blonde on Blonde, and the move redefined what a rock songwriter could be.
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Scott Walker (singer)
Born
Scott Walker was a screaming-fan teen idol with the Walker Brothers in the mid-1960s, then left the group for orchestral solo albums of Jacques Brel songs and his own dark songwriting. After years in the wilderness he returned with the unsettling avant-garde records Tilt (1995) and The Drift (2006), trading pop stardom for a lasting cult reputation.
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Joni Mitchell
Born
Joni Mitchell's Court and Spark (1974) was her biggest commercial success, and she followed it by moving steadily towards jazz with The Hissing of Summer Lawns, Hejira and Mingus (1979), made with the bassist Charles Mingus. Sales and reviews dipped at the time, but those records are now among her most admired.
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Steve Martin
Born
Steve Martin was playing arenas as the most popular stand-up comic in America when he gave up live comedy in 1981 to concentrate on films. His dark musical Pennies from Heaven flopped that year, but All of Me, Roxanne and Planes, Trains and Automobiles followed, and he later added novels, plays and Grammy-winning bluegrass banjo.
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Neil Young
Born
Neil Young answered his move to Geffen Records with Trans (1982), a vocoder-heavy synth album, and then a rockabilly record, Everybody's Rockin'. Geffen sued him in 1983 for making music unrepresentative of himself, and although the records baffled fans, he kept following his instincts and returned to acclaim with Freedom (1989).
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George Michael
Born
After the global success of Faith, George Michael made Listen Without Prejudice Vol. 1 (1990) and refused to appear in its videos, famously casting supermodels to mime Freedom! '90 instead. He then sued Sony to escape his contract and lost in 1994, a costly fight that ended only when other labels bought out his contract in 1995.
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Kylie Minogue
Born
Kylie Minogue left the Stock Aitken Waterman pop that made her famous for the indie label Deconstruction, and with Impossible Princess (1997) worked with Manic Street Preachers' James Dean Bradfield on an experimental, personal record. It sold modestly in Britain at the time but is now a fan favourite, and it preceded her dance-pop comeback with Light Years (2000).
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Jim Carrey
Born
Jim Carrey was the highest-paid comic actor of the mid-1990s on the back of rubber-faced hits such as Ace Ventura and The Mask. He chose Peter Weir's The Truman Show (1998), Miloš Forman's Man on the Moon and Michel Gondry's Eternal Sunshine of the Spotless Mind (2004), restrained performances that won him two Golden Globes and a new kind of respect.
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Garth Brooks
Born
Garth Brooks was the best-selling solo artist in America when he released Garth Brooks in... The Life of Chris Gaines (1999), a pop-rock album sung as a fictional alter ego for a planned film. The film was never made and the record was widely seen as a misstep, but it remains a rare example of a country superstar risking his image for an artistic experiment.
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Thom Yorke
Born
After OK Computer made Radiohead the most acclaimed guitar band in the world, Thom Yorke steered the group away from guitar rock towards electronic textures and fragmented lyrics. Kid A (2000) was released with no singles or conventional videos, topped the US chart regardless and is now widely ranked among the best albums of its decade.
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Adam Sandler
Born
Adam Sandler's broad comedies were reliable hits when he took the lead in Paul Thomas Anderson's Punch-Drunk Love (2002), a tense, tender study of a lonely man. He returned to that territory with the Safdie brothers' Uncut Gems (2019), whose frantic performance drew the best reviews of his career, while keeping his comedy audience alongside.
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Dave Chappelle
Dave Chappelle walked away from Chappelle's Show in 2005 during production of its third season, leaving behind a reported $50 million deal with Comedy Central and travelling to South Africa. He later said he was uneasy about how some sketches were being received, and he rebuilt his career on his own terms through stand-up, returning to large-scale specials from 2017.
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Daniel Radcliffe
Born
While still playing Harry Potter, Daniel Radcliffe took the demanding lead in Peter Shaffer's Equus on stage in London in 2007, and after the films ended he chose odd, risky projects such as Kill Your Darlings, Swiss Army Man and Weird: The Al Yankovic Story. A Tony Award for Merrily We Roll Along in 2024 confirmed a stage career built on choices few child stars dare to make.
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Joaquin Phoenix
Born
Fresh from an Oscar nomination for Walk the Line, Joaquin Phoenix announced in 2008 that he was quitting acting for hip-hop, and spent more than a year in public as a mumbling, bearded version of himself. Casey Affleck's I'm Still Here (2010) revealed it as a staged performance, and he returned with Paul Thomas Anderson's The Master (2012) and a run of uncompromising roles.
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Robert Pattinson
Born
Robert Pattinson could have stayed a franchise heartthrob after the Twilight films, but he deliberately sought out difficult directors: David Cronenberg for Cosmopolis, the Safdie brothers for Good Time, Robert Eggers for The Lighthouse and Claire Denis for High Life. When he did return to a blockbuster, as The Batman (2022), it was with a reputation for daring work.
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Kristen Stewart
Born
Kristen Stewart moved from Twilight to European art cinema, and for Olivier Assayas's Clouds of Sils Maria (2014) became the first American actress to win a César. Personal Shopper, Spencer, which earned an Oscar nomination, and Love Lies Bleeding followed, and in 2025 she made her feature directing debut with The Chronology of Water.
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Hugh Grant
Born
Hugh Grant spent two decades as the stammering romantic lead of British comedy and said openly that he had grown tired of it. From Florence Foster Jenkins (2016) he switched to vain, comic or sinister character parts: the villain in Paddington 2, Jeremy Thorpe in A Very English Scandal and a menacing recluse in Heretic (2024), the most interesting work of his career.
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