In the winter of 2015, when the State Tretyakov Gallery celebrated the 150th anniversary of the birth of Valentin Alexandrovich Serov (1865-1911) with a retrospective of his paintings, almost half a million people flocked to see them. The show was so popular that Muscovites queued for up to four hours in temperatures below −10°C (there were ambulances on standby), and the museum set up a field kitchen serving hot drinks and food. Among the 250 works on show – mostly portraits of the aristocracy, industrial magnates and the cultural beau monde – was one of an unidentified colonel with a penetrating gaze and an air of melancholy. It is offered by Bonhams at The Russian Sale in London this December.

Serov was the greatest Russian portrait painter of his generation, as well as the most valuable (his auction record stands at $14.5m), but he did not set out to flatter his subjects: he was interested in their souls. Look at his treatment of Princess Olga Orlova, now in the State Russian Museum in St Petersburg. Her hat may be splendid, her posture elegant and her fur decorously, even saucily, draped to reveal one marmoreal shoulder – one can’t help thinking of Sargent’s Madame X – but her eyes bulge, her nostrils flare and her expression exudes hauteur. As Serov wrote, “Each time I appraise a person’s face, I am inspired, you might even say carried away, not by his or her outer aspect, which is often trivial, but by the characterisation it can be given on canvas.” As the artist’s daughter, Olga, recalled in her memoir, “Everyone was afraid of his all-seeing eye.” Not to mention the number of sittings he demanded, which could run to 100 or more. As Serov himself said of Vera Mamontova, the 12-year-old subject of Girl with Peaches (1887), “I painted [her] for over a month and tortured her, poor child, almost to death.”

Valentin Alexandrovich Serov (1865-1911). Portrait of a Colonel, 1911, oil on canvas. Estimate on Request

In 1906, Léon Bakst painted this Portrait of Sergei Diaghilev with His Nanny. Bakst designed costumes for Diaghilev’s Ballets Russes

Valentin Serov, Children painted in 1899, housed in the State Russian Museum, St. Petersburg.

That did not discourage the great and the good from submitting to his scrutiny. He painted Tsar Nicholas II three times, and might have continued to do so had he not witnessed the massacre of Bloody Sunday in January 1905 from a window of the Academy of Arts. “A calm, proud and unarmed crowd marching towards gunfire and cavalry was a horrifying sight,” he wrote. “Who commanded this massacre?” He never again worked for the imperial family. A painter of landscapes, genre and historical scenes as well as portraits, Serov was 31 when he was invited to record the coronation at the Cathedral of the Dormition in the Kremlin in May 1896. Very much in the Impressionist style, that painting is crowded with figures. It shows the Tsar in ermine, stooped and in profile on the far left of the immense canvas, as he is anointed, his eyes obscured by a handkerchief held by one of the presiding metropolitans.

Nicholas was sufficiently pleased, however, to sit for Serov twice more, once in his pomp in the full-dress uniform of the Royal Scots Greys, the British regiment of which he was colonel-in-chief, and once at ease in the greatcoat of a life guard in the Preobrazhensky Regiment. This time Serov paints the Tsar not as an absolute monarch but as a man. By then, painter and subject evidently got along. Indeed, Serov passed on the news that Mir Iskusstva (World of Art), the magazine the great impresario Diaghilev had founded, was in financial difficulties. “‘But I have no head for finance,’ confided Serov to Nicholas. ‘Neither do I,’ said the Tsar”, who nevertheless invited him to apply to the chancery for a grant. On 4 June, the first of three annual payments of 15,000 roubles “was transferred to the editorial staff”.

More than a magazine, Mir Iskusstva was the art movement out of which the Ballets Russes grew. And Serov continued to be involved. He drew dancers – Mikhail Fokine, Tamara Karsavina, Vaslav Nijinsky, Ida Rubinstein (a rare nude) and Anna Pavlova (en arabesque in her Les Sylphides costume) – as well as Diaghilev. He designed the curtain for a production of the Rimsky-Korsakov ballet Scheherazade, and collaborated with Léon Bakst, a friend from his student days, on the sets for a production of the opera Judith, written by Serov’s father, the composer Alexander Serov in Paris in 1909.

Serov had grown up in an artistic milieu. His father – who considered himself the Russian Wagner – died when he was six, but his mother Valentina Serova, also a composer, would take Valentin Alexandrovich with her when she travelled in Europe. In 1874, mother and son settled in Paris. Here they met the distinguished Russian artist Ilya Repin, who began to teach the nine-year-old. This training led to a place at the St Petersburg Academy of Arts when Serov was just 15.

Repin introduced the young Serov to railway magnate and patron of the arts Savva Mamontov (who was the father of Vera, the Girl with Peaches), on whose Abramtsevo estate he lived for much of his youth. Here Mamontov had created a kind of artists’ colony, attracting painters (among them Korovin, Levitan, Nesterov, Polenov and Vrubel); composers such as Rimsky-Korsakov; and people from the theatre, notably the director Konstantin Stanislavsky.

Mamontov was not Serov’s only plutocratic patron. By the turn of the century, he was also a regular at the lavish Sunday lunches held by Mikhail Morozov at his mansion on Moscow’s Smolensky Bulvar. Morozov and his brother Ivan were scions of a family of prodigiously wealthy textile-manufacturers, and collectors on a grand scale. And Ivan began to consult Serov on their acquisitions.

It was Serov, for example, who suggested Ivan buy Bonnard’s Mirror Above a Washstand from the Salon d’Automne in 1908, one of 13 paintings by the PostImpressionist that Morozov came to own – and one of 200 of the Morozovs’ paintings currently on display for the first time outside Russia at the Fondation Louis Vuitton in Paris (until 22 February 2022). The following year, Serov also encouraged his acquisition of two van Goghs: The Red Vineyards and Prisoners Exercising. But not every artist the Morozovs revered found favour with Serov. When he painted Ivan in 1910, Serov sat him in front of the gloriously colourful Fruits and Bronze, one of a pair of Matisses Morozov had recently acquired from the artist for 5,000 francs a piece.

Morozov found them “amazing”, he told Matisse in his thank-you letter. Ever candid, Serov begged to differ, conceding Matisse had “talent” and “nobility”, but finding “no joy” in his work. “Technically [his] paintings are good, but something is lacking – they are vapid.” He was no more enthusiastic about Manet, and when Morozov was offered The Rue Mosnier with Flags, Serov dismissed it, first by telegram, then in a letter as “uninteresting. All it amounts to is a hastily painted sketch of the Paris streets on some political celebration of the July revolution.” This time Morozov took his advice. (The painting is now in the Getty Museum.) No wonder the critic Abram Efros called Serov “wilful” and his friends nicknamed him “Surov”, from the Russian for harsh, stern or severe.

So perhaps it is no surprise that the greatest of Serov’s portraits are sombre and introspective. Take his painting of the veteran actress Mariya Yermolova, whom Stanislavsky considered the greatest he had ever seen and for whom Chekhov wrote Platanov. Dressed in austere black, her expression impassive, she faces away from the viewer against a monochromatic background that reduces the architectural features of her evidently splendid central-Moscow apartment to minimally rendered geometric forms. But the most striking detail is the low viewpoint that forces the viewer to look up at her, as if seated in the stalls, gazing up at the stage. The subject of the painting offered by Bonhams – Portrait of a Colonel – maintains eye contact with the viewer. He sits against a black background that is entirely empty, as flat and dense as Malevich’s Black Square, which it precedes by four years, in total contrast to the loose, almost Impressionist brushwork of the uniform.

Painted in 1911, the year of Serov’s death from heart disease aged just 46, the colonel is evidently a distinguished soldier and a wealthy man. (Serov commanded fees of at least 5,000 roubles a painting.) His rank, polkovnik, is evident from his epaulettes, and the decoration denotes him as a member of the Order of St Vladimir 4th Class. But he is wearing a field blouse rather than the dress uniform one tends to see in military portraits, and his posture is slumped, his head resting heavily on his hand. Though his beard and close-cropped hair are kempt, his clear green eyes (a colour Serov also uses to highlight the grey in his beard) are sunken, his skin reddened by exposure (or drink), and his expression is world-weary. This is an image suffused with fortitude and resignation, and a fine example of the genius with which Serov was able to capture and convey character.

Claire Wrathall writes about art and travel for the Financial Times and other publications.

Serov’s Portrait of Sergei Diaghilev dates to 1904. The artist managed to secure fundng from the Tsar for the Ballets Russes founder’s journal Mir Iskusstva

Serov’s most famous work is Girl with Peaches of 1887. It is recognised as a ‘masterpiece of Russian art'