Friar Filippo Lippi’s Madonna has a secret, but not the one you think.

Madonna and Child with Two Angels was completed between 1460-1465, and this has become his most famous painting and one of the favorites of the oft repeated theme of the Virgin Mary and baby Jesus. Between you and me, I find the angels a little creepy and the baby Jesus a bit...sleepy? Drunk? But there’s a great story behind the piece, and that combined with Mary’s pearly crown and blue velvet dress are enough to reel me in.

At first glance, this work appears to be just another Madonna and child portrait, although skillfully rendered and very detailed. However, the relaxed nature of the angel in forefront and the intimacy between the mother and child made this portrait somewhat unprecedented when it hit the scene in the mid 1400’s. Some of the classic elements are still present, like their halos, signifying their holiness, and Mary’s hands clasped in prayer as a symbol of her piety and her act of charity in sacrificing her son. Her expression is somewhat classic as well, not smiling or particularly joyful presumably because of the divine knowledge that her son would die a terrible death. But unlike many portraits of the virgin, Mary does not look into the eyes of the viewer in confrontation, but instead enjoys the moment of joy she has with her son. This intimacy was what made the portrait so popular, but also so so juicy.

Until recently, there was absolutely no doubt in most art historians’ minds that the woman who modeled for this portrait was Friar Lippi’s lover, the nun Lucrezia Buti. You may be wondering Wait...aren’t nuns and friars supposed to be celibate?! You’re totally right! That was kind of a no-no.

Lucrezia and Filippo met when he became the headmaster of her nunnery, Santa Margherita. Some speculate they first got to know each other when she was modeling for paintings in surrounding Prato. We know some basics about the couple. The year Lippi became chaplain of her nunnery, she and her sister moved out of their convent and into Lippi’s cottage. By 1457, they had a son named Filippino. We don’t have first hand accounts of their relationship, and therefore can’t know much about how power played into the whole thing or if they were simply in ~LoVe~. However, Filippino’s will shows Lucrezia and Filippi also had a daughter together and it’s generally agreed that they lived in sin (not married) until Lippi’s death.

There’s no actual proof that this blonde babe is Lucrezia, but most scholars from an earlier time LOVE to speculate that Buti was modeling for this painting, and many other Lippi pieces. Given that the portrait was painted after the birth of his son in 1457, even art historians now can’t deny that at the very least some of the intimacy of watching Lucrezia raise their new son Filippino must have influenced Lippi.

Lippi painted a multitude of Madonnas but this is his most popular with art history buffs, because of its excellent execution in the rendering of faces, sensuous fabrics, and architectural elements. It is also the favorite because of the relaxed and serene intimacy between the Madonna and child, and the impish nature of the little angels. Many art historians cite this painting as one of the earliest intimate depictions of the Virgin and Child, and symbolic of a bigger change in the church. . Eventually more portraits like this became popular, and Lippi is to thank for that.

Not all Madonnas are created equally, and this one depicting a rebellious nun will stay at the top of my list.