[2][3] In February 2015, Pootsmann took part in the sixth season of Eesti otsib superstaari, an Estonian version of Pop Idol airing on TV3.

On 15 November 2015 he released the single "Aga Siis", peaking at number one in the Estonian Airplay Chart.

In 2016, Pootsmann was announced as one of the candidates in the Estonian national selection, Eesti Laul 2016, for the Eurovision Song Contest 2016.

On 20 February 2016 Pootsmann performed his song "Play" during the second semi-final of the selection at the Estonian Television studios in Tallinn, and he progressed to the final.

The final took place on 5 March 2016 at the Saku Suurhall in Tallinn, hosted by Ott Sepp and Märt Avandi.