My Top Ten Favourite Portrait Paintings

It’s been a long time since I flexed the old Art History muscles, but I do have a degree in the field, and it’s high time I do something with it (even if it’s just a silly blog post!)

In no particular order, here are some of my favourite portrait artists and an example each of their work. All of the works I chose to share in this list I would classify as classical portrait painting. I tend to enjoy naturalistic work (although I have a penchant for Minimalism.) However, I also selected these simply because my own style is naturalistic. I find these works personally relatable and also accessible to people who may not have studied Art History. And without further ado:


Self Portrait, Rembrandt Van Rijn, c. 1628

I love the way Rembrandt handles light and dark. It’s what he is known for, and with good reason. The way his subjects emerge from the shadows into the light is nothing short of magical. He worked very successfully at times as a portrait artist, and was known for his etchings, which also played extensively with light and shadow. Although he experienced much commercial success in parts of his career, he also encountered much hardship later on. Throughout, his style shifted, but his self-portraits were an ongoing reflection of the self throughout his years as a painter – there are more than 90 documented portraits of the artist, spanning from the 1620s until his death in 1669. I can only hope to be so prolific!


Fray Hortensio Félix Paravicino, El Greco, 1609

El Greco was a visionary of his time, now widely appreciated, but not entirely understood by his contemporaries. His expressionistic work echoed some of the qualities of Byzantine portraiture – the long pronounced fingers and hands, for example – but also incorporated elements of Italian Renaissance painting and Mannerism. His style, some say, is so unique to him that it defies categorization in any conventional school – and in fact, is seen by many as a precursor to Expressionism and Cubism. I’ve been lucky enough to see some of El Greco’s paintings in the flesh and they are unbelievably rich and moving. It’s no wonder he was such a game-changer in the art scene.


The Daughters of Edward Darley Boit, John Singer Sargent, 1882

John Singer Sargent was an American painter, who trained and spent most of his life in Europe. I find his work so appealing – it shows some Impressionist influences with broad and loose brushstrokes, but has almost photographic accuracy. I really love it. I chose this particular painting because I myself do a number of child portraits and I find this to be a really nice example. I enjoy the way in which each girl is separately highlighted and treated as an individual portrait, while the group as a whole works harmoniously.


Kent, Chuck Close, 1970

I cannot tell you how many times I stood in front of this megalith of a painting at the Art Gallery of Ontario during my years in art school in Toronto. Chuck Close’s larger works are completely mesmerizing to me, much in the way that Mark Rothko’s pieces are. I can stand back and view the piece as a whole, but when I stand closer, in its shadow, so to speak, the art consumes me, swallows me. Due to its size, at close range, the work is abstracted, and many of his works are even pixelated into irregular shapes within a grid when viewed up-close. (The grid features prominently in much of his process and resulting work.) His innovative and unusual techniques with colour and layering are even said to have inspired the invention of the first InkJet printer.


Dana Gordon, Alice Neel, 1972

Alice Neel’s portraits of artists, friends and other comrades are ripe with emotion and intensity. Dana Gordon’s is no different. She captures his expression with a seemingly effortless command of the paintbrush. This and Neel’s other subjects make very direct – even piercing – eye contact with the viewer, drawing us into their world and psyche. There is a rawness to these portraits. I find them very compelling.


Georg Gisze, Hans Holbein the Younger, 1532

I was again fortunate enough to view some of Holbein’s work in Europe while traveling over there several years ago, and it is quite enchanting. The technical skill is undeniable, from the absolutely tactile rug draped on the table at which Gisze sits, to the exactness of his face and hair. But what I also find so intriguing is the wealth of objects (and clothing) that represent the subject’s life as a merchant. Many of these objects are also symbolic. The vase sitting precariously close to the edge of the table, for instance, represent the fragility of life, while the carnations therein represent Gisze’s engagement. I could get positively lost in the details.


Self Portrait, Phillipe Auguste Renoir, 1899

This painting isn’t typical of Renoir’s well-known colourful Impressionist works, but I think it is a beautiful and telling self portrait. Perhaps I’m reading too much into it, but the darker palette to me suggests some sadness, which would make sense, given that the artist developed rheumatoid arthritis around 1892. He eventually moved to warmer climes, but was so debilitated by his arthritis, that he had to bandage his hands and strap a brush to his fingers. He also used a picture roll, due to his very limited mobility, to continue to paint larger pieces. Nonetheless, he continued to make art, right up until his death.


Portrait of Maude Abrantes, Amadeo Modigliani, 1907

I find this painting so beautiful and unusual. It predates the simplified, geometric figures for which Modigliani is more well-known, but hints at what was to come. The figure’s neck is elongated, her expression somber. Although there is some detail in the woman’s clothing, it is still fairly abstract. If I’m totally honest, I much prefer Modigliani’s earlier portraits, but his influence on modern art and Cubism is undeniable.


Girl With a Pearl Earring, Johannes Vermeer, c.1665

This painting is actually a “tronie,” or a depiction of a head that wasn’t intended to be a portrait of a specific person. Perhaps this is why the identity of the sitter remains unknown. However, it is such a beautiful specimen of work, and conveys so much feeling about the girl that I had to include it. Vermeer was a master of light and colour, often depicting his subjects near windows, with natural light pouring in on them. I love how this girl is bathed in light, but shown against a solid, dark background. It is visually striking and irrefutably soft and beautiful.


Self Portrait, Lucien Freud, 2002

Lucien Freud was certainly a preeminent painter of the 20th century. His work is deeply psychological and often jarring. Not surprisingly, connections have been made between him and his very famous grandfather Sigmund Freud. For instance, his figures often recline on a couch or settee, which has been speculated to be a nod toward his grandfather and the therapist’s couch. He also had an interesting way of working, in which he would start by painting the subject’s head, and work out from there, intentionally leaving a section of the canvas blank until the end, as a reminder that the piece was in progress. Toward the end of the portrait, he would return to the head, as his knowledge and understanding of the sitter at that point would be deeper. So, a psychological connection with important in his working process. The results are often uncomfortably intimate.

This was an interesting exercise for me and a bit of a walk down Memory Lane. Thanks for reading. I’ll give some thought to putting together a list of pet portraits too. Might be fun!

xo melody

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