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Madonna's ex shares rare photos of star with short hair

Sun, October 18, 2026 - 23:45
3 min
Madonna's ex shares rare photos of star with short hair

Archival photos of Madonna taken by her ex-boyfriend Dan Gilroy are being discussed online. The pictures show the future star with short dark hair and wearing casual clothes in New York, according to the Instagram account History Photographed.

What is known about Madonna's archival photos in New York

The photos were taken in 1979, when the future star was a dancer just beginning her career. At the time, her life was closely connected to musician Dan Gilroy, who took the pictures.

After they started dating, Madonna moved into an old synagogue in Corona, Queens, where her boyfriend lived and worked with his brother Ed.

In the photos, Madonna is seen on a bus wearing a sweatshirt, green cargo pants, sneakers, and a short haircut. In these photos, the singer looks completely different from the famous stage look she is known for today.

How Madonna started her music career

While the brothers worked as waiters during the day and performed comedy at night, Madonna was learning to play the drums and beginning to write her first songs.

Dan taught her to play the guitar. They later formed the band Breakfast Club. Madonna initially played the drums before starting to perform her own songs.

In 1980, she left Breakfast Club and formed her own band, Emmy and the Emmys.

How Madonna's relationship with Gilroy ended

The couple's professional and personal relationship lasted around 18 months in total. Their breakup was caused by differences in their views of the future and their ambitions. Madonna wanted to pursue a solo career and eventually took steps in that direction.

After their relationship ended, Gilroy kept personal photographs, videos, and love letters Madonna had written to him during a trip to Europe. Some of this archival material was used in the documentary Madonna and the Breakfast Club, released by director Guy Guido in 2019.

In September 2024, the musician told People that he had initially planned to auction the letters along with musical instruments Madonna had used early in her career. However, she asked him not to make them public. In return, the singer autographed the instruments, and Gilroy returned the letters.

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