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Madonna Dear Jessie cover shot by Herb Ritts

Madonna is one of the most influential and successful pop stars in music history. Her career spans over four decades, and she has sold over 300 million records worldwide. I’ve been a fan since her first single through to “Confessions on a Dance Floor” after which I didn’t keep up.

Her first hits – Borderline, Lucky Star and Holiday still sound so fresh today. I didn’t buy her self-titled debut album was released in 1983 but did then buy and love Like a Virgin, True Blue and Like a Prayer on vinyl. Her ‘reinvention’ with Ray of Light was incredible and so too was ‘Confessions on a Dancefloor’ which remains the perfect Saturday night album.

As part of my globe trotting postcard collection, I found a number of Madonna cards to go on the pile. From this collection we can see so many different persoane she adopted over the years!

I love her work with Herb Ritts. They first worked together in the mid-1980s, when he photographed her for the cover of her third album “True Blue” and the single “Open Your Heart.” Over the years, Ritts and Madonna collaborated on a number of iconic photo shoots, including the famous image of Madonna in a black bustier and gloves from the “Express Yourself” video.

Ritts also directed several of Madonna’s music videos, including “Cherish,” “Love Don’t Live Here Anymore,” and “Bye Bye Baby.” He was known for his ability to capture Madonna’s beauty, strength, and vulnerability in his photographs and videos.


I am Jay, the founder of Wine, Travel and Song. UK based, I set this blog up in 2016 to share my passion for food & drink, travel and music - Wine, Travel & Song. In these posts I share some of my passions in the hope that it may inspire you to go there, eat that or listen to this. In return I hope you will comment and share recommendations of where to go, what to eat and what to listen to!