Curated playlist

21st-century American singer-songwriters

Bob DylanAt a 1966 Manchester concert, Bob Dylan told his band to play loud after a heckler called him Judas.
Britney SpearsBritney Spears sold the rights to her entire music catalogue for a reported $200 million. The buyer was the music publisher Primary Wave, and the BBC reported that the purchase closed on the 30th of December 2025. The price reflects a body…
MadonnaMadonna arrived in New York in 1978 with thirty-five dollars. It was her first plane ride and first taxi.
Lady GagaLady Gaga's name may have come from a phone typo. Producer Rob Fusari said autocorrect turned "Radio Ga Ga" into "Lady".
Kate HudsonKate Hudson reached the end of a long awards season in 2025 with a striking comparison. Her first brush with acclaim, she said, had felt like a "shock entrance, or invitation, into this world." This time was different. When you have been…
Bruce SpringsteenBruce Springsteen threw the first acetate of his own album Born to Run into the swimming pool of his hotel in 1975. The record was being mastered while the band toured, and he was furious at what he heard. He briefly considered scrapping…
Janet JacksonJanet Jackson was seen at the 1983 American Music Awards wearing a hoop earring with a key attached to it. She has worn variations of that earring in music videos and live shows ever since. The pair she wore between 1987 and 1990 is now on…
Bruno MarsBruno Mars was five years old when he wet himself on a Honolulu stage in the middle of Elvis Presley's "Can't Help Falling in Love." His parents wondered whether they were making a mistake by putting him in front of crowds. He never…
Justin TimberlakeJustin Timberlake was 11 years old when he appeared on the television show Star Search and sang country songs under the name Justin Randall. The boy from Memphis, Tennessee would one day be dubbed the Prince of Pop. Billboard would name…
Paul SimonPaul Simon, the American singer-songwriter and guitarist, nearly gave one of his best-known songs the wrong name. While writing music for the film The Graduate, he toyed with calling a new song "Mrs. Roosevelt." Art Garfunkel passed the…
James BrownJames Brown pointed out band members' wrong notes with hand signals.
Fergie (singer)Fergie, born Stacy Ann Ferguson, sang on a song that held the top spot on the Billboard Hot 100 for 14 straight weeks in 2009. That song, "I Gotta Feeling," stayed at number one longer than any other song that year. By then her records had…
Tom WaitsTom Waits accepted his place in the Rock and Roll Hall of Fame in 2011 with a joke at his own expense. “They say that I have no hits and I'm difficult to work with. And they say that like it's a bad thing!” The man who inducted him, Neil…
Brie LarsonBrie Larson's 2005 album Finally Out of P.E. sold only 3,500 copies. She later won the Academy Award for Best Actress.
Johnny CashJohnny Cash never served a prison sentence. He was jailed seven times, one night each.
Missy ElliottMissy Elliott and Timbaland wrote and produced nine tracks on Aaliyah's 1996 album One in a Million.
Brian WilsonOn a flight to Houston in 1964, Brian Wilson broke down sobbing. He then quit touring with the Beach Boys.
Jerry Lee LewisJerry Lee Lewis feared his own hit song was blasphemous.
Cyndi LauperCyndi Lauper wore almost a pound of necklaces to the Grammy Awards ceremony in 1985. The excess suited the woman wearing it. Lauper is an American singer, songwriter and actress, born on the 22nd of June 1953. She is known for eccentric…
Iggy PopIggy Pop, born James Newell Osterberg Jr., built a reputation on rolling around in broken glass while a crowd watched. Admirers eventually called him the "Godfather of Punk". His first band sold few records, yet its songs outlasted much of…
Alanis MorissetteAlanis Morissette recorded a demo cassette in August 1989 and sent it to Geffen Records. The tape has never been heard. It was stolen, along with other records, in a burglary of the label's headquarters in October 1989. Whatever it held is…
Ariana GrandeAriana Grande organized a benefit concert after the Manchester Arena bombing. It raised $23 million.
Kendrick LamarKendrick Lamar won the Pulitzer Prize for Music in 2018, the first for a piece outside classical and jazz.
Steven TylerSteven Tyler, the singer born Steven Victor Tallarico, saw his touring career end in August 2024. That month, his band Aerosmith announced that it was retiring from the road. The reason was Tyler's voice. He had fractured his larynx and…
Hayden PanettiereHayden Panettiere was eleven months old when she first appeared on screen, in a 1990 advertisement for a Playskool toy train. That commercial was the start of a working life that now spans several decades. How does an infant in commercials…
Don HenleyDon Henley told interviewer Charlie Rose in March 2001 that "rock bands work best as a benevolent dictatorship." He knew the arrangement from the inside. Henley is a drummer, singer and songwriter, and a founding member of the Eagles. In…
Miley CyrusMiley Cyrus was eight years old when she grabbed her father's arm in a Toronto theatre. In 2001 the family lived in Toronto while Billy Ray Cyrus filmed the television series Doc. He took her to see a Mirvish production of Mamma Mia! at…
Hilary DuffHilary Duff was a child actor cast in the pilot of the NBC comedy Daddio, and producers removed her from the cast before it aired. A week later she won the title role in a new Disney Channel series. Years after that, in 2026, Time named…
Lindsay LohanLindsay Lohan posed for the October 2010 cover of Vanity Fair and then made a blunt request. "I want my career back," she told the magazine. She added, "I know that I'm a damn good actress." The plea carried weight because Lohan, an…
Kid RockKid Rock, born Robert James Ritchie in Romeo, Michigan, was 17 when he signed with Jive Records. Years later, his album Devil Without a Cause sold 14 million copies. Both facts belong to one career, and little else about that career is…
Lana Del ReyLana Del Rey was born Elizabeth Woolridge Grant, and for years she performed under names that almost nobody remembers. One of them was Sparkle Jump Rope Queen. Another was May Jailer. These were the stage identities of a young American…
Stevie NicksStevie Nicks, born Stephanie Lynn Nicks on the 26th of May 1948, could not pronounce her own name as a toddler. The best she could manage was "tee-dee", and that slip turned into the nickname Stevie. Decades later, Rolling Stone placed her…
Patti SmithPatti Smith, the American singer, songwriter, poet and author, lost her place in the middle of a song at the Nobel Prize Award Ceremony in Stockholm. The date was the 10th of December 2016. She was standing in for Bob Dylan, winner of the…
Christina AguileraChristina Aguilera sang "A Sunday Kind of Love" on the television contest Star Search in 1990 and was eliminated in the semi-final round. That loss decided nothing. She would go on to sell more than 100 million records worldwide, and…
Dolly PartonDolly Parton refused to give Elvis Presley half the publishing rights to "I Will Always Love You."
Megan Thee StallionMegan Thee Stallion's mother took her to recording sessions instead of daycare.
Axl RoseAxl Rose, the lead singer of Guns N' Roses, was ninety minutes into a July 1991 concert at the Riverport Amphitheater near St. Louis when he decided to deal with a problem himself. He had asked security on stage to confiscate a fan's video…
Trent ReznorTrent Reznor once worked at Right Track Studio in Cleveland as an assistant engineer and janitor. Studio owner Bart Koster remembered his employee this way: "He is so focused in everything he does. When that guy waxed the floor, it looked…
Reba McEntireReba McEntire, later known as the Queen of Country, nearly missed her Grand Ole Opry debut on the 17th of September 1977. A guard at the gate overlooked her name on the list of performers. Her parents and her older sister Alice had driven…
Alicia KeysAlicia Keys was fifteen years old when Columbia Records tried to win her signature with a $26,000 white baby grand piano. She took the deal. It began a long struggle over who would decide what her music sounded like. Years later she summed…
Kelly ClarksonKelly Clarkson's first single debuted at number 60 on the Billboard Hot 100 in the United States. The following week it rose to number 52. Then it shot to number one, breaking a record for the biggest leap to the top that The Beatles had…
Billie EilishBillie Eilish was 18 years old when she left the 62nd Annual Grammy Awards in 2020 holding all four of the ceremony's general field prizes. Only one person had done that before her, and no woman had. Not long before, she had been a…
Billy JoelWilliam Martin Joel, better known as Billy Joel, left Hicksville High School in 1967 without a diploma. He had missed a crucial English exam after playing a late-night gig at a piano bar, where he earned money to help support his mother…
Gwen StefaniGwen Stefani had a hit in 2005 that changed how Americans bought music. Her single “Hollaback Girl” rose to number one on the Billboard Hot 100. It also became the first song downloaded one million times in the United States. The woman…
Demi LovatoDemi Lovato, an American singer, songwriter and actress, sang the national anthem at Super Bowl LIV in 2020. Eighteen years earlier, in 2002, Lovato was a child playing a character named Angela on the children's series Barney & Friends.…
Jack AntonoffJack Antonoff is an American musician from New Jersey who once heard the same dismissal again and again. He later put it in his own words. "Taylor's the first person who let me produce a song. Before Taylor, everyone said: 'You're not a…
Willie NelsonWillie Nelson plays a classical guitar with a hole worn through its face. Decades of strumming with a pick have scoured a wide sweep of wood away beside the sound hole. Classical guitars are made for fingers, so this one has no pickguard…
Neil DiamondNeil Diamond, born on the 24th of January 1941, once stretched his food budget to just 35 cents a day. Decades later, the American singer-songwriter had sold more than 56.5 million records in the United States alone. That total places him…
Anthony KiedisAnthony Kiedis was born on the 1st of November 1962, and as a young man he walked on stage with a band that existed to play one song, one time. The group called itself Tony Flow and the Miraculously Majestic Masters of Mayhem. Its only…
Addison RaeIn October 2025, Addison Rae walked onto the stage of The Tonight Show with Jimmy Fallon wearing a sparkling gold gown. The burlesque star Gypsy Rose Lee had first worn that gown in the 1950s. Rae put it on to sing "Diet Pepsi", the song…