The singer, 65, took to Instagram to share a video to her 19 million followers of clips and photos from the event.
Rocco, 23, held the joint exhibition with Luigi and Iango, an Italian fashion photography duo who have beautifully captured numerous celebrities over the years - including Madonna.
Budding artist Rocco approached the model, American Lynley Eilers, while smoking a cigarette. They stood on a small stage surrounded by candles and an orchestra.
Lynley then took the cigarette from him and he began to paint her completely naked body, bar a white base coat, with reds, yellows, and blues.
Madonna was every ich the proud parent as she watched her eldest son Rocco Ritchie paint a nude model at his art show in Milan on Sunday
The singer, 65, took to Instagram to share a video to her 19 million followers of clips and photos from the night, including Rocco painting a nude model
Rocco painted American model Lynley Eilers who wore an extravagant, long, and bushy ginger wig
Madonna captioned the post: 'A Magical Evening at The Palazzo Reale ! The Exhibition of @luigiandiango was amazing ⚡️⚡️⚡️
'But to watch my son Rocco's paint a model live @lynleyeilers was Truly a magical experience while musicians played Ravel's " Bolero" — A. moment I will never forget! Bravo @roccoritchie . ♥️
'I am so proud of you and certainly the luckiest Mom in the world! Thank you to everyone who made it possible! Especially @luigiandiango @palazzorealemilano @dolcegabbana @abramovicinstitute
Rocco co-founded his own gallery called Maison Rhed, the name taken from his alias Rhed which he used at the beginning of his career.
The talented artist told Vogue Hong Kong that although neither of his parents are painters, they fostered a love of art in him from a young age.
He said: 'It certainly helped growing up in a house that was passionate about art and culture.
'Neither of my parents are painters, but both are artists in their own right and they taught me to appreciate and respect it. Their shared fascination eventually piqued my interest and since I can remember I've always been surrounded by it.'
Rocco is Madonna's only biological son, conceived with her second husband, Guy Ritchie.
There were previously reports of a strained relationship between Rocco and Madonna, due to Guy and Madonna's custody battle, but all seems to be behind them.
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Rocco approached the model, American Lynley Eilers, while smoking a cigarette. They stood on a small stage surrounded by candles and an orchestra
Lynley then took the cigarette from him and he began to paint her completely naked body, bar a white base coat, with reds, yellows, and blues
Rocco co-founded his own gallery called Maison Rhed, the name taken from his alias Rhed which he used at the beginning of his career
The talented artist told Vogue Hong Kong that although neither of his parents are painters, they fostered a love of art in him from a young age
Madonna wrapped Rocco in a tight hug after the show
There were previously reports of a strained relationship between Rocco and Madonna, due to Guy and Madonna's custody battle, but all seems to be behind them
Madonna was in Milan for the Italian leg of The Celebration Tour which began in October and is due to end in April
Madonna was in Milan for the Italian leg of The Celebration Tour.
The tour is Madonna's twelfth, but is the first to not be in support of a new album, instead revisiting Madonna's old hits.
A celebration of Madonna's forty-year career, Ecommerce The Celebration Tour began on 14 October in London and is due to end on 24 April in Mexico City.
Madonna was forced to cancel some dates when she was rushed to Intensive Care to treat a bacterial infection in June.
Rocco RitchieMadonna
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