[6] In 2014 he competed and won the Singer/Songwriter in the category in the Italian festival Il-Cantagiro with his own song "Ti Amo, I Love You".

[7][8] In 2015, Jas Rolyn teamed up with four other local singers, and competed as the group L-Ilħna with the original gospel song "Qalbien" in the Maltese Festival Għanja Gmiel Is-Seba' Noti (organised by Erseb Productions).

The track was written by Matt 'Muxu' Mercieca, mixed and mastered by Cyprian Cassar (former member of Tenishia).

Later on in July, together with his sister Shyli Rose and the duo K13, Cassar performed live with the orchestra and competed in the Semi-Final of L-Għanja tal-Poplu,[12] with their hip-hop track "Tama" (hope) which was co-written by Jas Rolyn.

Rolyn's single spent 6 weeks in the MVTV's Top 20, reaching its highest spot #11 on 5 November.

On 14 April 2019, Rolyn released his debut record Journey To Freedom alongside the music video of Chained (ft. Shyli Rose).