Any of the great portrait painters in the History of Art may have had some sympathy with Schopenhauer’s remark above. To distil a person’s entire being into one single face, whether it be painted in oils or drawn with charcoal, is a true test of the perception of an artist. Whether painting emperors, kings, courtiers, artistic friends, or oneself, the best painter’s never fail to interrogate as well as flatter their sitters both visually, intellectually and emotionally.

The Hotung Evening Sale features works by some of the most significant portraitists in the History of Art. With works spanning no less than four centuries, these five pictures exhibit an enormous breadth. As a group, they document the infinitely varying ways artists have approached capturing the likenesses and characters of their sitters.

Beginning in the seventeenth century, Sir Anthony Van Dyck’s superb and intimate Portrait of Lucas Van Uffel (estimated £400,000 - £600,000) is a technical masterpiece of how little paint is required to capture a portrait in the grand manner. The artist’s grisaille, undertaken using just two colours, has been noted as scholars as the benchmark against which all Van Dyck’s sketches for his famous Iconographie series may be judged.

Turning from Antwerp to Haarlem, Fran’s Hals’s Portrait of a man, three-quarter-length, wearing black with a white collar (estimated £600,000 - £800,000) was created at the height of the artist’s powers during the years 1634-5. Known for creating one of the most famous painted faces in London, The Laughing Cavalier preserved at the Wallace Collection, Hals’s male portraits were innovative during his lifetime. His bold and confident brushwork, features of his immediately recognisable style, are evident here in abundance and affords this unknown sitter a remarkably living presence.

Moving into the nineteenth century, Édouard Vuillard’s Autoportrait dans un mirroir (estimated £500,000 - £700,000) is a striking performance at one of the most difficult of all portrait types. Created when the artist was barely twenty years old, Vuillard here attempts that most vital and trying process of self-interrogation with paint. The psychological undertones witnessed here sets the tone for all portraits of the modern age, which peer beneath the facades of flesh and bone to deeper truths.

Henri Matisse’s Tête de femme (Madame Paley) (estimated £600,000 - £800,000) builds on increasing primacy of the line and geometric shapes. The artist’s use of charcoal here is perfectly suited in capturing the effortless elegance of his sitter Dorothy Paley, once regarded as the world’s best-dressed woman. Reducing Paley’s spellbinding beauty to its essentials in a spontaneous manner, this work makes it clear why Matisse favoured the process of drawing rather than painting portraits.

Alberto Giacometti’s Portrait de Peter Watson (estimated £150,000 - £250,000) brings us full circle from Van Dyck’s intimate and economic grisaille. In this lightening fast pencil drawing it is quite possible to appreciate what has been described as the artist’s 'lifelong and admittedly hopeless struggle with reality'. In depicting the enigmatic collector and philanthropist Watson, Giacometti’s pencil is constantly exploring form and never settles for precision.