Born February 24, 1880 in Kharkov. His father was an employee of Botkin’s private firm, his mother ran the house. The sister is an artist of the Maly Theatre V.O. Massalitinova. Childhood and youth passed in Tomsk, gymnasist Massalitinov took part in amateur performances. In 1900 he entered the medical faculty of Tomsk University, for participating in a student demonstration was expelled from the university. He joined the Institute of Technology and was expelled from the institute for the same reason. In 1904, on the advice of his sister (by that time the actress of the Maly Theatre), he moved to Moscow and was admitted to the Moscow Imperial Theatre School in the class of A. A. Fedotov. Those present in 1907 at the graduation performance of the school K.S. Stanislavsky and Vl.I. Nemirovich-Danchenko invited him to the Moscow Art Theater.
In the Art Theatre he played Rock Tooth (Woe from the wit of A. Griboyedov), Doctor (Brand H. Ibsen), Third Worker (Drama of the Life of K. Hamsun). In 1907-1909 he played small roles in the premiere performances: Prince Vorotynsky and Prince Kurbsky (Boris Godunov A. Pushkin), Father (Life of a Man L. Andreev), Father and Buk (Blue Bird M. Meterlinka), Ukhovertov (Inspection Officer N. Gogol), Professor Gilling (At the Royal Gates of Hamsun), Islayev (Month in the village of I. Turgenev). Among the major roles Massalitinov: Claudius (Hamlet W. Shakespeare, 1911), Stanitsyn (Where thinly, there and tears Turgenev, 1912), Shatov (Nikolai Stavrogin by F. Dostoevsky, 1913), Zhivnovsky (Death of Pazukhin by M. Saltykov-Shchedrin, 1914), Rostanev (Village Stepanchikovo by Dostoevsky, 1917). He played more than 30 roles in the MHT. He was introduced into Chekhov's performances Three Sisters (Salty), Cherry Orchard (Lopakhin), in Gorky On the Bottom (Satin).
Massalitinov took part in the work of the 1st Studio of the Moscow Art Theater, in particular, he played the role of Alexei in the play Kaliki the passerby of V. Volkenstein (1915). In 1913, with N. Alexander and N. Podgorny, he opened a theater school (“School of the Three Nikolaevs”), the graduates of which united in the 2nd Studio of the Art Theater.
In June 1919, the Kachalov group (which included Massalitinov) was cut off from Moscow. Massalitinov, together with I. Bersenev and S. Bertenson, was on the board of the group. As a director, together with N. Litovtseva, he restored the performances of Autumn Violins by I. Surgucheva (Lavrov), At Life in the Hands of Hamsun (Bondesen), The Karamazov Brothers by Dostoevsky (Prosecutor), Three Sisters by A. Chekhov (Andrey), At the Bottom of Gorky (Satin). After the performances in Kharkiv, Odessa, Ekaterinodar, Tbilisi, Batuma "Kachalov group" Cherry Orchard opened a tour in Sofia on October 20, 1920. From January 18, 1921, performances continued in Belgrade, Zagreb, Ljubljana, and then in Prague. After the return of part of the group to Moscow, Massalitinov, along with the remaining actors, played in the Prague troupe, headed by M. Hermanova, in the City Theater.
In 1924, Massalitinov established a private theater school in Berlin, in 1925-1944 the chief director of the People's Theatre in Sofia. He became one of the leading figures of the Bulgarian scene.
Among Massalitinov’s productions of Western drama are W. Shakespeare’s Twelfth Night (1925), H. Kleist’s Prince of Homburg (1942), Shakespeare’s Hamlet (1943), and Hernani V. Hugo (1943). From the Russian classics - Woe from the mind of A. Griboyedov (1930), Poverty is not a vice of Ostrovsky (1932), At the bottom of Gorky (1932), Ostrovsky's Bezpridannitsa (1937), Gorky's Enemies (1944), Chekhov's Three Sisters (1953), Talents and Fans of Ostrovsky (1955). Massalitinov considered the creation of a national repertoire his main task. He staged many plays by Bulgarian authors: Master R. Stoyanov (1927), Albena (1929), Millionaire (1930) and Ordinary Man (1936) by I. Yovkov, The Abyss and Throne of I. Vazov (1934), The Struggle Continues by K. Kyulavkov (1946) and others. He staged performances in other theaters in Bulgaria and Yugoslavia, and continued to play on stage. The approval of the scenic principles of the Moscow Art Theater was facilitated by the pedagogical activity of Massalitinov. In 1926 he established a school at the People's Theatre (since 1948 - the Institute), for many years Massalitinov was a professor of the school. In 1948 he was awarded the title of People's Artist of Bulgaria. Laureate of the Dimitrov Prize (1950).
Massalitinov died in Sofia on March 22, 1961.