1. Madonna delle Roccie by Fra Filippo Lippi (1465)
I had the great fortune of seeing the original of this one at the Uffizi Gallery on a trip to Florence. Ever since, I've been mesmerized by the beauty of the painting. A copy even graces the entry way to my home.
2. Madonnina by Roberto Ferruzzi (1897)
While Ferruzzi didn't intend to paint Our Lady, this lovely painting immediately gained fame as a devotional portrait. The simplicity with which "La Madonnina" (The Little Madonna) is attired, her gaze heavenward, and the halo-like glow surrounding her (and her child) struck Nineteenth Century Italians as worthy of La Madonna herself.
3. Madonna del Berdone by Coppo di Marcovaldo (1261)
This Madonna holds a special place in my heart as it takes the best of Eastern Iconography and puts a decided step in the direction of the great Renaissance masters to come. Coppo shows Our Lady in her heavenly glory, which is a nice reminder in this day and age, when the temptation to portray Mary as little more than a regular teenage girl (which of course she once was) overwhelms many more recent images.
4. Our Lady of Gaudalupe by Miraculous Image (1531)
No list of Marian pictures could be complete without what might be the most widely familiar (and miraculous) image of them all. The story, of course, is a well known one. The appearance to St Juan Diego. The incredulity of the bishop. The unfolding of the tilma. The shock (which can still be seen on Mary's eyes, under intense magnification) on the bishop's face. The inexplicable image. The conversion of the Americas.
5. The Virgin of the Immaculate Conception by Diego Velazquez (1619)
Here we see Our Mother simultaneously as a girl of thirteen and as the reigning Queen of Heaven. She is surrounded by her crown of stars and gazes down upon us poor sinners as we offer up supplications for her prayers. Her she is at once holy and human. As I gaze upon her gentle face, I'm left glorifying God, who so loves His creatures that He shares with us (and most especially with her) the task of building the Kingdom.