What 20 iconic musicians looked like when they were in their 20s

What 20 iconic musicians looked like when they were in their 20s
  • Many of today's well-known musicians looked very different in their 20s.

  • While in their 20s, Diana Ross, Madonna, and Elton John all released No. 1 songs.

  • Other musicians, like Joni Mitchell and Bob Dylan, found greater success later in their careers.

Stevie Wonder already had two songs reach No. 1 by the time he was 21.

stevie wonder
Stevie Wonder taught himself how to play three different instruments.AP and Willy Sanjuan/Invision/AP

Stevland Hardaway Judkins, known as Stevie Wonder, was born in 1950 in Michigan with an eye disorder that left him blind.

While in his 20s, Wonder released a few albums, including "Talking Book," which featured songs like "You Are the Sunshine of My Life" and "Superstition," both of which hit No. 1 on the Billboard charts.

At age 23, he was in a near-fatal car accident that left him in a coma for a few days. Fortunately, the musician was able to recover and he put out four more albums before his 30th birthday.

Now in his 70s, Wonder continues to perform music and advocate for people who are blind.

By the time he was in his 20s, Mick Jagger was already part of a successful band.

mick jagger
Mick Jagger joined The Rolling Stones when he was around 19 years old.Mario Anzuoni/Reuters and Robert Dear/AP

Now a rock legend, Mick Jagger was born Michael Phillip Jagger in 1943 in England.

At around 19 years old, Jagger joined The Rolling Stones with longtime friend Keith Richards and four other musicians.

The Rolling Stones took off in Jagger's 20s with the launch of the band's debut album in 1964 and first No. 1 international hit in 1965, "(I Can't Get No) Satisfaction."

Today, Jagger is in his 80s, and The Rolling Stones are still performing.

Throughout her early 20s, Gloria Estefan was part of the Miami Sound Machine.

gloria estefan
Gloria Estefan was the lead singer of Miami Sound Machine.Paul Natkin / Getty Images and Demetrius Freeman/Reuters

Gloria Estefan was born Gloria Fajardo in 1957 in Havana, Cuba.

As a teenager, she met future-husband Emilio Estefan, and he asked her to join the Miami Latin Boys. Shortly after, the band was renamed Miami Sound Machine, and she became the lead singer.

After numerous hits including "Rhythm Is Gonna Get You," the band became known as Gloria Estefan and the Miami Sound Machine.

In 2016, she and her husband received the Presidential Medal of Freedom to honor their contributions to American music.

Now in her 60s, Estefan continues to play music. But she's also written two children's books and one cookbook, and she produced the Broadway musical about her career "On Your Feet."

While in his 20s, Paul McCartney released 12 studio albums with The Beatles.

paul mccartney
Paul McCartney started the Beatles with John Lennon.AP and Amy Harris/Invision/AP

Born James Paul McCartney in 1942 in England, McCartney has spent his entire adult life playing music professionally.

As a teenager, he joined John Lennon to form a band that eventually became The Beatles.

Throughout his early and mid-20s, McCartney found great success with iconic hits like "Can't Buy Me Love," "Eight Days a Week," and "Let It Be."

By the time The Beatles officially broke up in 1970, they had released 12 albums. That same year, shortly before he turned 30, McCartney released his first solo album.

Now in his 80s, McCartney continues to make and perform his music.

Madonna launched her music career when she was in her 20s.

Madonna's first single was "Everybody."AP and Jeenah Moon/Reuters

Nicknamed the "Queen of Pop," Madonna was born Madonna Louise Veronica Ciccone in 1958 in Michigan.

When Madonna was in her 20s, she launched her music career with the song, "Everybody."A few years later, her album "Like a Virgin" reached no. 1 on the Billboard charts.

Now in her 60s, Madonna released her most recent album, "Madame X," in 2019, and it debuted at No. 1 on the Billboard charts. The singer is still performing live.

While in her 20s, Dolly Parton released some of her biggest hits.

dolly parton then and now
Dolly Parton made a name for herself in country music.Michael Ochs Archives / Stringer/Getty Images and Lucy Nicholson/Reuters

Born in 1946 in Tennessee, Dolly Parton grew up as one of 12 children. She first found some success at age 21 when she joined "The Porter Wagoner Show," which was a musical variety series.

While in her 20s, Parton signed a record deal and churned out classic hits like "Jolene" and "I Will Always Love You."

Now in her 70s, Parton is focused on her philanthropic work. As part of her organization, Dolly Parton's Imagination Library, she has donated millions of books to children.

In 2019, she also executive-produced "Dolly Parton's Heartstrings," a Netflix anthology series inspired by her extensive music catalog. In 2020, she wrote, produced, and starred in the holiday film "Dolly Parton's Christmas on the Square."

In his 20s, Bob Dylan released one of his most famous songs.

bob dylan
Bob Dylan has a Presidential Medal of Freedom.AP and Dave J Hogan/Getty Images for ABA

Iconic folk singer-songwriter, Bob Dylan was born Robert Allen Zimmerman in 1941 in Minnesota.

He got his big break at 20 years old after one of his shows received a positive review in the New York Times.

A few years later, in 1964, Dylan released "The Times They Are a-Changin'," which quickly become an anthem for people protesting the Vietnam War.

In 1966, he was reportedly in a near-fatal motorcycle accident, though there have been many mysterious and contradictory details about it shared over the years. Following the reported incident, he stepped out of the spotlight and was rather quiet for about a year.

He released music again in December of 1967 and found increased success in his 30s.

Now in his 80s, Dylan has received multiple awards, including the Presidential Medal of Freedom in 2012 for his contribution to American music and the Nobel Prize in Literature in 2013 for his lyrics, making him the first songwriter to win the award.

Carlos Santana played Woodstock shortly after he turned 20.

carlos santana
Carlos Santana performed at Woodstock in 1969.Michael Ochs Archives / Handout/Getty Images and Amy Harris/Invision/AP

Born in 1947 in Mexico, Carlos Santana was the son of a professional musician and was encouraged to learn the violin from an early age. That instrument never stuck, but he eventually developed a passion for the electric guitar.

And in 1966, he formed the Santana Blues Band (later known as Santana) that played a blend of Latin rhythm, rock, and blues.

In his early 20s, Santana played at Woodstock and caught the attention of producers from Columbia Records.

Santana experienced a resurgence of popularity in 1999 after a collaboration with Rob Thomas on the single "Smooth." That year, he won eight Grammy Awards.

Now in his 70s, he continues to create and perform music.

By the time he turned 30, Elton John had already released multiple No. 1 songs.

elton john
Elton John has been rocking his signature colored frames since his 20s.Michael Putland/Getty Images and Denis Balibouse/AP

Elton John was born Reginald Kenneth Dwight in 1947 in England. He taught himself how to play the piano when he was a child, a skill that landed him a scholarship to the Royal Academy of Music in London.

In his 20s, John responded to a newspaper ad looking for a songwriter, which ultimately led to his partnership with longtime songwriting companion, Bernie Taupin.

The pair put out classic songs like, "Your Song," "Crocodile Rock," and "Bennie and the Jets."

By the time he turned 30, John had multiple no. 1 songs on the Billboard charts.

Now in his 70s, John wrapped up his Farewell Yellow Brick Road tour. He said it will be his last one.

He also helped create his Oscar-nominated biopic, "Rocketman," which debuted in 2019 and received stellar reviews.

While in his early 20s, Willie Nelson worked as a DJ.

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Willie Nelson studied farming before becoming a musician.Michael Ochs Archives/Getty Images and Harrison McClary/AP

Born in 1933, Willie Nelson grew up in Texas where his musical interests were encouraged by his grandparents.

During his early 20s, Nelson studied agriculture at Baylor University while working as a DJ at a radio station. At 27, he moved to Nashville where he became a songwriter for other musicians.

But Nelson didn't find mainstream success as a singer until he was in his 40s and his song, "Blue Eyes Crying in the Rain," reached no. 1 on the country music charts and earned him a Grammy.

Now in his 90s, Nelson works as an animal-rights activist while continuing to put out new music. He also published a memoir, "Willie Nelson's Letters to America."

Tina Turner became a lead singer in her early 20s.

tina turner
Tina Turner was the lead singer of the Kings of Rhythm. Michael Ochs Archives/Getty Images and Vianney Le Caer/Invision/AP

Iconic R&B singer Tina Turner was born Anna Mae Bullock in 1939 in Tennessee. In her early teens, she moved to St. Louis, Missouri, where she was fully introduced to the R&B music scene.

She launched her music career in her 20s when she recorded "A Fool in Love" for the Kings of Rhythm.

Two years later, she married Kings of Rhythm leader, Ike Turner, and worked with him to release new music and hit covers of songs like "Proud Mary."

In 1978, Tina divorced Ike, alleging that he physically abused her throughout their relationship. He died in 2007.

In 2018, she released her second autobiography, "My Love Story," and received a lifetime achievement award at the Grammys.

Tina died at the age of 83.

At 27 years old, Joni Mitchell saw commercial success with the release of her second album.

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Joni Mitchell started her career in the folk genre.RB/Redferns/Getty Images and Bruce Glikas/WireImage/Getty Images

Folk singer Joni Mitchell was born Roberta Joan Anderson in 1943 in Fort Macleod, Canada.

Mitchell began singing when she was 9 years old after contracting polio and being left bedridden.

After moving to the US, she released her debut album at age 25, but she did not see commercial success across genres until she released "Ladies of the Canyon" when she was 27 years old.

Throughout her career, Mitchell earned eight Grammy awards. She released her most recent album, "Shine," in 2007.

Now in her late 70s, she's been battling a number of health issues and has made few public appearances. But Brandi Carlile recently brought Mitchell on stage to perform with her during Newport Folk Fest in 2022.

Bruce Springsteen released "Born to Run" when he was in his mid-20s.

bruce springsteen
Bruce Springsteen is still recording top-10 hits.Jim Pozarik/AP and Star Shooter/MediaPunch /IPX

Born in 1949 in New Jersey, Bruce Springsteen first picked up a guitar after seeing Elvis Presley on "The Ed Sullivan Show."

He spent his early 20s playing local bars with his friends, who later became members of the E Street Band.

At 24 years old, Springsteen and his band put out their first record with mild success. Their real success came when "Born to Run" was released two years later, landing at No. 3 on the Billboard charts.

He received the Presidential Medal of Freedom in 2016 for his contributions to American music.

Now in his 70s, Springsteen is still making music. His 2019 record, "Western Stars," reached the top 10 on the Billboard 200 chart.

Springsteen released his 20th studio album, "Letter to You," in October 2020.

When he was 20 years old, Ozzy Osbourne joined Black Sabbath.

ozzy osbourne
Ozzy Osbourne was once the front-runner of Black Sabbath.Michael Ochs Archives/Getty Images and KGC-138/STAR MAX/IPx/AP

More recently known for his reality TV show, "The Osbournes," Ozzy Osbourne was born John Michael Osbourne in 1948 in England.

Throughout his teens, Osbourne said he struggled to keep a job and dabbled with "a bit of burglary" before getting caught after just a few weeks.

But in his 20s, Osbourne joined a band that would eventually become Black Sabbath. By the time the singer was 22, he and Black Sabbath had put out their first album, which charted in both the UK and US.

Throughout his 20s, Osbourne put out a number of heavy-metal albums with the band.

During the late 1970s, Osbourne was kicked out of the band because he missed weeks of practice and had been continuously engaging in erratic behavior that was fueled by drugs and alcohol, according to the BBC archives. He pursued a number of solo projects over the next few decades.

In 2002, Osbourne and his family starred in the MTV reality show, "The Osbournes," which focused on their daily lives. In the 2010s, he reunited with his Black Sabbath bandmates to release a final album and embark on one last tour.

Now in his 70s, Osbourne has been open about struggling with his health, but he is still releasing music and he plans to continue touring as soon as he is able.

Diana Ross was a successful musician and actress by the time she turned 30.

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Diana Ross was a member of The Supremes.Dave Pickoff/AP and Jordan Strauss/Invision/AP

Born in 1944 in Detroit, Michigan, Diana Ross became a member of the acclaimed Motown group, The Supremes, while in her teens.

By the time Ross turned 20, she and The Supremes had already released three no. 1 hits.

While in her mid-20s, Ross left the band to focus on her solo career and she quickly hit No. 1 with "Ain't No Mountain High Enough."

From there, she started to explore a career in acting, starring in "Lady Sings the Blues," which landed her an Academy Award nomination.

Now in her late 70s, she has received the BET lifetime achievement award, the Grammys lifetime achievement award, and the Presidential Medal of Freedom, for her contribution to American music.

The singer also recently collaborated with Saint Laurent by Anthony Vaccarello on a fashion campaign.

In his early 20s, Billy Joel released "Piano Man."

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Billy Joel was working as a lounge singer when he wrote "Piano Man."Michael Putland/Getty Images and mpi04/MediaPunch /IPX/AP

Billy Joel was born in 1949 in the Bronx, New York, and he started playing piano when he was a child.

Joel released his first album "Cold Spring Harbor" in 1971 and two years later, in 1973, while he was working as a lounge singer, he released the hit track "Piano Man," based on his experience.

He went on to release four more albums before he turned 30.

In 2013, he was inducted into the Kennedy Center Honors, an honor for individuals in the performing-arts world who make major contributions to American culture.

Now in his 70s, Joel has mostly retired from creating new music, but he continues to tour and play his hits.

While in her early 20s, Stevie Nicks opened for fellow music legends Jimi Hendrix and Janis Joplin.

stevie nicks
Stevie Nicks is best known for her time in Fleetwood Mac.Larry Hulst/Michael Ochs Archives/Getty Images and Evan Agostini/Invision/AP

Born Stephanie Lynn Nicks in 1948 in Arizona, Stevie Nicks was exposed to music at an early age by her grandfather. He had a love for country music and even made Nicks her own guitar.

In 1968, musician Lindsey Buckingham asked Nicks to join the band Fritz, and the group opened concerts for artists like Jimi Hendrix and Janis Joplin.

After disbanding and putting out some music of their own, Nicks and Buckingham both joined the group Fleetwood Mac in 1975.

That same year, while in her late 20s, Nicks released her first album with Fleetwood Mac and it featured iconic songs like "Landslide" and "Rhiannon."

It quickly rose to no. 1 on the Billboard 200 chart. In 1977, the band's next album "Rumours" also hit No. 1.

Throughout the 1980s and 1990s, Nicks put out more successful solo music and was inducted in the Rock and Roll Hall of Fame with her bandmates in 1998, and then as a solo artist in 2019.

Nicks reunited with Fleetwood Mac for a tour in 2018. Now in her 70s, she is still touring as a solo artist.

Smokey Robinson released his first hit when he was in his 20s.

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Smokey Robinson worked with Motown Records.Donaldson Collection/Getty Images and Kevork Djansezian/Getty Images

Called the "King of Motown," Smokey Robinson was born William Robinson Jr. in 1940 in Michigan. He founded The Miracles as a teenager, which led him to his ultimate success.

When Robinson was in his 20s, he and The Miracles had their first real hit with "Shop Around." He continued to release popular songs with The Miracles, including "You Really Got a Hold on Me" and "I Second That Emotion."

During this time, he was also working behind the scenes producing music with Motown Records.

Now in his 80s, Robinson continues to create and perform new music as a solo artist. In 2017, he released a Christmas album called "Christmas Everyday."

When he was 26 years old, Sting joined the Police.

Sting was the lead singer of the Police.Richard E. Aaron/Redferns/Getty Images and Jorge Guerrero/AFP/Getty Images

Sting was born Gordon Sumner in 1951 in England. He got the nickname "Sting" early in his music career because he used to wear a black-and-yellow-striped sweater that looked like a bee.

At age 26, Sting joined the Police, and the band saw some early success with the album "Reggatta de Blanc." Over the next few years, the Police's popularity soared with hits like "Don't Stand So Close to Me" and "Every Little Thing She Does Is Magic."

Throughout the 1980s and 1990s, Sting released numerous popular solo albums and acted in few movies, including "Dune" (1984).

In 2014, he also composed the music for the musical "The Last Ship," which is inspired by his childhood in England.

Now in his 70s, Sting is still performing. He released his latest album, "The Bridge," in 2021.

He also had a minor role on season one of Hulu's "Only Murders in the Building."

In his late 20s, Jimmy Buffett moved to Key West and found his beach inspiration.

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Jimmy Buffett is best known for "Margaritaville."Tom Hill/WireImage/Getty Images and Tim Mosenfelder/WireImage/Getty Images

Country musician Jimmy Buffett was born in 1946 in Mississippi. After graduating from the University of Southern Mississippi, he moved to Nashville to pursue a career in music.

In his mid-20s, Buffett released his first few albums but did not find much success. And in 1971, he moved to Key West, Florida, where he found inspiration in the tropical islands.

While in his early 30s, he released his beachy album "Changes in Latitudes, Changes in Attitudes" that included his iconic hit "Margaritaville" and cemented him in mainstream culture.

In the 1980s, he turned Margaritaville into a brand and started to expand it into merchandise and cafes.

Buffett continued to perform and release new music into his 70s. He also expanded the Margaritaville brand to include beach-themed resorts, retirement communities, and casinos.

The beloved singer died in September 2023.

This story was originally published on February 24, 2020, and most recently updated on January 19. 2024.

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