ʿAskarī’s musical interests date back to his primary school years when his Ḥaḍrami teachers urged him to sing songs by Ḥusayn al-Miḥḍār, the paramount lyricist of the Ḥaḍrami “school” of sung poetry. ʿAskarī’s singing talent was evident from an early age, and he was encouraged to collaborate with Muḥammad Bakhīt (“Abū Ṣabrī”), who wrote nationalistic poems in Arabic for him to sing. In 1975, ʿAskarī moved to al-Mukallā to study for the baccalaureate exam, where he also continued to sing and write his own Arabic-language poems for performance. During this time, ʿAskarī began to perform to the accompaniment of the ʿūd and violins played by Ḥaḍrami musicians; he brought this style of performance back to al-Mahra during his summer breaks when he would perform at wedding parties in Ḥawf. By the late 1970s, ʿAskarī had developed a stable group of musicians to accompany him: one or two ʿūd players, two drummers of the large “African” hāyir, an ʾīqāʿ (two small ṭablas joined together) and tambourine (daff) player, and one or two violinists. Collectively they became known as “ʿAskarī Ḥujayrān’s Band” (Firqat ʿAskarī Ḥujayrān). Because expertise with musical instruments was lacking in al-Mahra, all of the musicians who accompanied ʿAskarī were (and continue to be) from Ḥaḍramawt. Starting in the 1990s, ʿAskarī began to move away from nationalistic songs and collaborate with local Mahri poets (including Ḥājj Dākōn) who wrote “folkloric” (Ar. shaʿbī) lyric poetry in Arabic. According to his own testimony, ʿAskarī achieved a higher degree of artistic merit when he explored local melodies and the works of local poets (although he still restricted himself linguistically to the performance of songs in Arabic). His performances were very well received at this time, and he became very popular among local audiences. During the late 1990s, ʿAskarī added a synthesizer player to his band as well as someone capable of playing a type of mizmār known as the abū ʿashr (distinct from the larger, local mizmār played by the Mahri poet, musician, and singer from the 1970s, Bakhīt bir Ḳutrān).
According to ʿAskarī, the combination of locally derived, lyric sung-poetry and non-local instrumentation signaled the onset of a new “school” of Mahri poetry: the Mahri School. According to ʿAskarī, the Mahri School could be distinguished in its earliest stages only by the use of local rhythms and melodies and not by language, because Arabic was still the sole language of sung-poetry. This changed in the first years of the twenty-first century thanks to ʿAskarī’s collaboration with Ḥājj Dākōn and other Mahri poets who provided ʿAskarī with Mahri-language lyrics for him to perform. ʿAskarī’s performance of Mahri-language poetry has been very well received by local audiences (although unlike Muḥammad Mushaʿjil, ʿAskarī does not have a non-Mahri following). As of 2008, ʿAskarī has performed the following Mahri-language songs in public: “Everything About You Is Beautiful” by Ḥājj Dākōn, “I Want to Ask the Wedding Party” by Ḥājj Dākōn, Kel hābū yʾāǧēbem bīs by Gharīb Khamīs al-Kūsh, and Hōh hbērek ġeǧnōt tesyūr waḥśīs by Gharīb Khamīs al-Kūsh.
ʿAskarī’s collaboration with Ḥājj Dākōn has been particularly fruitful, and the two have worked together on a number of projects (although not without occasional personal friction). In an interview that Ḥājj Dākōn gave to the cultural magazine al-Thaqafiyya (217 : 11), Ḥājj has the following to say about their collaboration:
“I have worked with all the singers (fannānīn) living in al-Mahra, and collaborative efforts have brought us together…In particular, [I have worked with] the Mahri singer, ʿAskarī Ḥujayrān, who is like a factory of Mahri sung-poetry and who is its chief developer, having sung at and enlivened parties from an early age, even at a time when there were very few musical instruments and Mahri sung-poetry was unknown.”
For a detailed analysis of the collaboration of ʿAskarī and Ḥājj toward the creation of a new mode of Mahri sung-poetry (Liebhaber, 2011b).
In addition to his career as a performer, ʿAskarī collaborated with Alexander Sima in the publication of the monograph Mehri-Texte aus der jemenitischen Šarqīyah (Sima, 2009). This experience, including two years spent lecturing in Mehri at the Institute of Semitic Studies in Heidelberg, has given ʿAskarī the authority to speak more broadly about linguistic and sociolinguistic issues in al-Mahra. As a result, ʿAskarī is often called upon by local and national institutions to bring his expertise to bear on questions of Mahri language and culture.