At the same time Osipov attending evening classes of Tavricheskaya Art School, where he studied with famous teachers Vladimir Sukov and Semion Abugov.

About years of study Osipov left memories: Alexander Alexandrovich Osmerkin was, in my opinion, a born teacher who knew how, like no one else, to explain the difficulties encountered in the work, while finding surprisingly accurate, sometimes not direct, but giving food for thought words.

So, revealing to us the method of Cezanne, he compared it with the picturesque experience of Alexander Ivanov, and then Cezanne's “Mount St. Victoria ”with its transitions of clearly defined color plans – from warm pink and orange to blue and blue – becomes somewhere very close to the Italian canvases of our great Alexander Ivanov.

In the same year Osipov comes to Samarkhand to completed his studies in the Institute of Painting, Sculpture and Architecture in Alexander Osmerkin workshop.

His graduation work was painting named Partisans, dedicated to the guerrilla struggle against the Nazis in occupied territory of the Soviet Union.

Surgeons, including myself, in quilted jackets under dressing gowns, emaciated, sawed bones with difficulty.The wounded man slowly recovered, his life was saved.

The art critic Nadezhda Neshataeva spoke about the life of the artist Osipov Sergey Ivanovich in connection with a personal exhibition of his paintings.

For me and my friends, employees of our surgical department of the hospital, such a belated message about the fate of one of our seriously injured was not only a great joy, but also a reward for our selfless work in the besieged city.

From 1949 until the end of 1970 Osipov taught at the Department of General painting of the Leningrad Higher School of Art and Industry named after Vera Mukhina.

In 1983, with the support of E. E. Moiseenko, a large solo exhibition of Sergey Osipov's works was shown at the Central House of Artists in Moscow.

In the artistic fate of S. Osipov, which began from the work at diploma picture, which developed progressively, without visible zigzags and jumps, researchers distinguish several periods.

Every year trips from the late 1940s to Staraya Ladoga, Izborsk, Pskov, and Staritsa helped the artist to restore his creative skills and establish himself in a circle of preferred topics.

In the future, Osipov will practically abandon the presence of figures of people in the landscapes and the detailed reproduction of panoramic architectural views.

The work of Osipov was inextricably linked with the theme of the Motherland – the Tver land, its nature, ancient Russian cities, and the peasant way of life.

Since the end of the 1940s, he will annually, and often several times a year, travel to Staraya Ladoga, Izborsk, Staritsa, Torzhok, Pskov, bringing from these trips numerous studies, sketches and paintings.

By simplifying and light deformation of objects, Sergei Osipov emphasizes their three-dimensional structure, and internal force, the stress with which they have been created nature or man.

Another notable feature of his art becomes more abstract forms and the entire composition of the painting, a marked tendency to generalize, allegory, the desire to get away from naturalism to the contemplative and philosophical depth.

Tower of XVII Century (1967), Crossing over river, In Suzdal, Izborsk Ancient Town (all 1968), "Still Life with a Balalaika",[32] Silver villows, Wildflowers, Ravine.

Grey Day (all 1970), "House with Arch",[33] "Still Life with White Jug" (both 1972), "Autumn branch",[34] "Staritsa town in winter",[35] Landscape with Fortress, Winter in Staritsa (all 1974), "Cornflowers"[36] (1976), "A Forest River" (1976), "Izborsk's slopes" (1978), "Small rick in rainy day" (1981), "Early green" (1982), "Dandelions" (1985),[37] and others.

Having escaped from some overload of details in composition, which was encountered in his earlier works, Osipov achieves in still life a great depth of image and associativity of hidden subtext.

[38] In his paintings much comes from the art of ancient Russian masters: laconicism of the artistic language, conventionality of form and accuracy of composition, resourcefulness in details, integrity, and expressiveness of the image built on unpretentious peasant material.

By opinion of Svetlana Makhlina, small landscapes of Sergei Osipov are endowed with extraordinary power of influence on the audience.

In 2016, the Elena and Gennady Timchenko Charity Fund donated ten paintings by Sergei I. Osipov with characteristic views of ancient Russian cities and architectural monuments to the Yamalo-Nenets Museum and Exhibition Complex named after I. S. Shemanovsky (Salekhard).

In 2017, painting Autumn Branch (1974) by Sergei Osipov appeared in the TV series CHANCE shot by 20 Century Fox Film Corporation based on the novel of the same name by American novelist Kem Nunn, commissioned by American video streaming service Hulu with popular English actor Hugh Laurie in the title role.

In the final two episodes of the thriller ("A Madness of Two", and "Especially If You Run Away") written by Kem Nunn the painting Autumn Branch by Sergei Osipov is shown in the interior of the house of the protagonist Dr. Eldon Chance, played by Hugh Laurie.

Against the background of the painting, which plays a plot-forming role in these scenes, key dramatic dialogues unfold with the participation of the main characters of the film.