Over the years, Cutelilpineapple fostered a love for soundtracks from animation and video games, teaching herself to play them on the piano by ear or from sheet music. She began uploading piano covers and arrangements on YouTube under the channel "Cutelilpineapple" in 2016. A few years later, she transitioned into singing vocal covers of songs from her favorite JRPG OSTs, including Fire Emblem: Three Houses and Xenoblade Chronicles 3.