Though he converted to Russian Orthodoxy at an early age, Shapiro nonetheless retained lifelong ties to Judaism, Zionism, and his mitnagedic roots, themes of which featured prominently in his poetry.

[9][10] Shapiro recorded performances by Vasilii Andreev-Burlak for a photo series devoted to Nikolai Gogol's short story Diary of a Madman, published as an album in 1883.

His first published poem, "Me-Ḥezyonot Bat 'Ammi" ("From the Visions of the Daughter of My People", 1884–1898), garnered him a place in the foremost rank of Hebrew poets.

Shapiro's anthology Mi-Shire Yeshurun ('From the Songs of Jeshurun', collected in 1911) contains his most famous poem, "Beshadmot Beit-Leḥem [he]" ('In the Fields of Bethlehem'), in which Rachel grieves for her sons as she walks up from her grave toward a silent Jordan River.

The poem, set to music by Hanina Karchevsky, became a popular anthem of labour Zionism and the basis for a well-known Israeli folk dance.

[17] Other poems of Shapiro include "Amarti Yesh Li Tikvah," a translation of Friedrich Schiller's "Resignation", and "Sodom", an allegorical description of the Dreyfus affair.

[8] Shapiro died in 1900 in St. Petersburg, leaving several tens of thousands of rubles to the Odessa Committee, which supported Jewish settlements in Palestine of the First Aliyah.