National Portrait Gallery art: Seven paintings you need to see

Ailis Brennan
National Portrait Gallery, London

The National Portrait Gallery offers plentiful fodder for art lovers – and history buffs, music lovers, bookworms, the politically charged and the fashion forward.

From monarchs to Olympians, musicians to scientists, likenesses of some of the most recognisable faces in the world have been collected by the National Portrait Gallery, to the tune of 11,000 portraits overall.

If you’re short on time, these are the five paintings you shouldn’t miss at one of London’s most famous galleries.

William Shakespeare associated with John Taylor feigned oval, circa 1600-1610

He's the most celebrated writer in history, and has written some of the most quoted epithets in English Literature – but there is still a lot we don’t know about William Shakespeare. The image of Shakespeare as a ruff-wearing, quill-brandishing, long-haired rake is ingrained in our perception of him, but we actually have very little evidence of what he looked like. This portrait, known as the Chandos Portrait, is the only artwork considered by experts to have likely been painted of the playwright from life.

Queen Elizabeth I by Unknown continental artist circa 1575

(National Portrait Gallery London)

Elizabeth I, the daughter of Henry VIII, nearly didn’t become Queen at all – but when she did, she made it count. As she rallied her troops to fight off the Spanish Armada, she famously said “I know I have the body but of a weak and feeble woman; but I have the heart and stomach of a king, and of a king of England too.” She ruled for 44 years, never married, and fixes us in this painting with an authoritarian stare, dressed in a masculine-style doublet.

Kelly Holmes by Craig Wylie 2012

(National Portrait Gallery London)

The National Portrait Gallery isn’t just for historical figures, but a chance to celebrate those making a change here and now. As well as bringing home two Olympic gold medals in 2004, Dame Kelly Holmes has also been a sergeant in the British army, and the founder of a charity seeking to support young people through sport. At nearly 2 metres tall, the work manages to be both imposing and intimate, and displays a remarkable dedication to hyperrealism, with every pore of Holmes’ skin explored.

Lord Byron replica by Thomas Phillips circa 1835, based on a work of 1813

(National Portrait Gallery London)

When it comes to literary characters, you would be forgiven for believing Lord Byron to be a fictional one. The Romantic poet and politician travelled the world, became a Greek national hero after fighting the Ottoman Empire, had affairs with an astounding number of women, died at just 36 and was famously summed up by lover Lady Caroline Lamb as “mad, bad and dangerous to know”. Byron sat for this portrait wearing Albanian dress, and was one acclaimed by his contemporaries for its likeness.

Anne Boleyn by Unknown English artist late 16th century, based on a work of circa 1533-1536

(National Portrait Gallery London)

We all know Henry VIII had six wives – and that they all met various ends. Anne Boleyn, the Tudor king’s second wife and mother of Elizabeth I, was not one of the lucky ones. Henry created an entire new church to allow himself to marry her but, just three years later, he ended up accusing her of adultery, incest and plotting to kill him, before having her beheaded. Although painted after her death, this portrait is thought to be derived from a contemporary one, and captivates viewers with Boleyn’s eyes, which were said to be “black and beautiful”.

Sir Anthony van Dyck by Sir Anthony van Dyck circa 1640

(National Portrait Gallery London)

Anthony Van Dyck is one of the most acclaimed royal portraitists of all time. His masterful likenesses of Charles I and his family are not just historically important artefacts, but are considered outstanding artworks in their own right. This self-portrait, one of just three by the Flemish artist, was saved for the nation in 2014 . The attention to detail brings a piercing realism to his face, a contrast to the broader strokes on his dress. This disparity suggests either that the painting is unfinished, or that Van Dyck was experimenting with his use of paint in this informal work.

Amy Winehouse ('Amy-Blue') by Marlene Dumas 2011

(Marlene Dumas; courtesy of the artist and Frith Street Gallery, London)

The dreamlike quality of South African painter Marlene Dumas’ work here captures singer-songwriter Amy Winehouse. Dumas, who never paints directly from life, took the image of Winehouse from one of the many shots of her in the press. The mix of intimacy and distance provokes us to consider how well we know her iconic image alongside how well we know the troubled individual. The posthumous portrait is tinged blue, as a nod to both the difficulties she faced in her short life, and the influence she took musically from blues and jazz artists.