30 Rarely Seen Photos of Amy Winehouse as a Teenager in the 1990s

“I have this dream to be very famous. To work on stage. It’s a lifelong ambition. I want people to hear my voice and just, forget their troubles for 5 minutes. I want to be remembered for being a singer, for sell-out concerts and sell-out West-End and Broadway shows. For being just... me.” – An extract from Amy Winehouse’s audition letter for the Sylvia Young Theatre School, 1997.

Born in 1983, Winehouse grew up in North London in a Jewish family with a deep connection to music. Her father, Mitch, was a huge fan of Frank Sinatra and other Rat Pack singers, and her mother’s family included several professional jazz musicians. Winehouse was exposed to a wide range of genres from a young age, including jazz, soul, and R&B, with artists like Ella Fitzgerald, Dinah Washington, and Sarah Vaughan being key influences.

When she was 10, Winehouse and her best friend, Juliette Ashby, formed a short-lived rap duo called Sweet ‘n’ Sour, inspired by the hip-hop group Salt-N-Pepa. Winehouse was “the sour one.” This early venture demonstrated her creative spirit and interest in music from a young age.

Amy’s talent led her to enroll at the prestigious Sylvia Young Theatre School at age 12. However, she was later expelled for “not applying herself” and for getting her nose pierced—a sign of her rebellious nature that would later become a part of her public image. Following this, she briefly attended the BRIT School.

By her mid-to-late teens, Winehouse was beginning to find her voice as a performer and songwriter. She bought her first guitar at 14 and started writing her own songs. She sang with local jazz bands in North London and performed with the National Youth Jazz Orchestra.

By the end of the decade, a demo tape of Winehouse’s was sent to a record company scout by a close friend, singer Tyler James. This crucial step led to her signing with Simon Fuller’s management company, 19 Entertainment, in 2002, and ultimately to a record deal with Island Records. While her career truly took off in the early 2000s, the 1990s were the period where Amy Winehouse cultivated her unique sound and set the stage for her future success.