Samiilenko was best noted as a satirist for his combination of poetry and political humour, and he was praised by intellectual leader Ivan Franko for his usage of lyricism.

Born in modern-day Poltava Oblast to a serf and a landowner, Samiilenko was a polyglot, and began his career in literature and translation while studying in gymnasium.

While a student at Saint Vladimir Imperial University of Kiev, Samiilenko became involved with several groups supporting the Ukrainian national revival.

He was the son of Ivan Lysevych, a landowner, and Oleksandra Samiilenko, a serf, and was raised by Oleksii Trokhymovskyi, a close friend of the family of Nikolai Gogol.

Several of the group's members would go on to become leading writers during the late 19th and early 20th centuries, among them Lesya Ukrainka, Olena Pchilka, Mykola Lysenko, and Mykhailo Starytsky.

During his interactions with the latter group, he became acquainted with leading Ukrainian intellectuals such as Ivan Franko, Leonid Hlibov, Borys Hrinchenko, and Mykhailo Kotsiubynsky.

[4] At the turn of the century, he had also begun to write comedic plays, such as A Drama Without Horilka (1895), The Uncle's Disease (1896), and In Haikhan-Beia (1897), all of which were critically acclaimed.

[4] In 1906, Galician Ukrainian intellectuals Ivan Franko and Mykhailo Mochulskyi created an anthology of Samiilenko's poems, publishing the collection in Lviv[2] with the title of Ukraine.

The death of his two sons in infancy (the second in 1911) strongly impacted Samiilenko, who wrote to Yevhen Chykalenko, "Now a great grief has befallen me, before which both debts and the loss of all property pale."

He was working as a freelance translator in an effort to accrue a liveable income, and he was living under the care of Vira Matushevska, the widow of Rada's chief editor Fedir Matushevskyi [uk].