How Old 14 Iconic Women Were When They Got Their Big Break

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We all have a tendency to think that the sooner we have our shit together, the sooner we’ll become rich, famous and successful. But sometimes that’s just not the case.

Some of the most iconic women of all time didn’t make it their first shot, while others were born bound for fame. So, we compiled a list of some of our favorite women and when they got their big break. Some of these may stress you out (like WTF am I doing with my life) and others may relieve you.

1. Madonna – 24

A far cry from the tweenage Disney-approved pop stars of today, Madge made it on the pop scene when she was 24 in 1982 and struck her first solo record deal. She released her first self-titled album in 1983, which produced her first breakout hit “Holiday.” Celebrate!

2. Cindy Crawford – 16

Cindy won the “Look of the Year” contest in 1982, which was held by the Elite Modeling Agency when she was only 16, which basically jump-started her career. Only five months after that, she was on the cover of Vogue. Ugh, must be nice.

3. Marilyn Monroe – 24

While her teenage husband was deployed, Marilyn was 18 and working in a factory inspecting parachutes. One of the army photographers in 1944 took a photo of her for an advertisement, and by the next year, Marilyn had already appeared on 33 magazine covers. She signed a contract for her first movie role when she was 20, but did not break out in any major films until 1950 when she was 24 and appeared in six major films that year.

4. Billie Holiday – 18

After moving to NYC with her mom and working in a prostitution house, Billie Holiday was discovered at age 18 by producer John Hammond while performing in a Harlem jazz club. John partnered her with an up-and-coming clarinetist and bandleader Benny Goodman, and they recorded several tracks, including her first commercial release “Your Mother’s Son-In-Law”.

5. Oprah – 32

The TV host got her start at age 22 after moving from Nashville to Baltimore to begin hosting a TV chat show called “People Are Talking.” The show was a hit and she hosted it for 8 years before getting recruited to host a show in Chicago. Then at age 32, Oprah hit it big with her own self-titled show where she morphed into the bread-loving Oprah we know and love today!

6. Dolly Parton – 25

Dolly was born into a very poor family in Tennessee. She got her first guitar from a relative, and begin writing songs at age 10. The songs were so fantastic that she started performing in Knoxville, and then three years later appeared on the Grand Ole Opry Stage at age 13. She finished school, and she got her big break when she got her first number one country single at age 25 in 1971.

7. Meryl Streep – 28

Although her career began on the stages of New York in the 60s, she didn’t hit her big break until 1977 she was 28. She starred in the film “Julia” with Jane Fonda, and people really started noticing her after that. She landed many roles after that, including “The Devil Wears Prada” in which she is the villainous Miranda Priestley.

8. Cher – 19

Cher moved to Hollywood when she was only 16 to pursue a career when she met Sonny Bono at a coffee shop. The two worked together, and eventually fell in love. They made their break out album and record in 1965 with “I Got You Babe” when she was only 19.

9. Joan Rivers – 32

After realizing that acting wasn’t her thing, she spent many years performing in New York’s coffee houses and comedy clubs. Joan’s big break finally came around when she was 32 and she booked a gig on “The Tonight Show With Johnny Carson” in 1965. She was a smash hit, and that eventually led to her hosting her own show.

10. Tina Turner – 21

When Tina moved to St. Louis in her early teens, she became obsessed with the R&B scene there. In 1956, she met Ike Turner, and began performing with his group called the Kings of Rhythm. In 1960, when Tina was 21 years old, one of the lead singers for the “Kings of Rhythm” didn’t show up to a recording session, so she took the spot and sang one of the lead songs called “A Fool in Love.” The group sent the demo to a New York radio station, and it instantly became a hit.

11. Winona Ryder – 17

As a teenager, Winona attended the American Conservatory Theater in San Francisco. She made her film debut when she was just 15 in the film “Lucas” in 1986, and then in 1988, Tim Burton cast Ryder in “Beetlejuice” when she was 17, which is where she really took the spotlight. She then went on the star in other cult classics like the “Heathers.”

12. Amy Winehouse – 23

When Amy was 12, she was accepted into the highly regarded Sylvia Young Theatre School in London, and also received her first guitar in that same year. However, when she was 16, she was expelled from that school, but one of her friends, up-and-coming pop star Tyler James, passed her demo onto his label. That led to her record deal with Universal/Island records. Her debut record Frank in 2003 led to success in the UK, but her second record “Back to Black” in 2006 gave way to her most successful hit “Rehab” when she was 23.

13. Britney Spears – 17

Brit was only 11 when she started on the Mickey Mouse Club, starring alongside other bound for fame stars like Justin Timberlake and Christina Aguilera. Then in 1998, her biggest hit, “Baby One More Time” came out when she was 17, basically assuring her route to pop-star fame.

14. Whitney Houston – 22

Whitney was discovered when she was 19 by record tycoon Clive Davis, and he signed her almost immediately. She released her debut self-titled album in 1985 at age 22 and almost overnight became a pop sensation, and became one of the most iconic voices of all time.


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