The literal image - singing so loudly the song pierces the clouds - comes from 《
列子·
汤问》 in the famous story of the singer Qin Qing (
秦青), whose voice was said to 'shake forests and stop drifting clouds' (
响遏行云). The set phrase
高唱入云 itself is recorded in the Han-dynasty 《
西京杂记》 and means praise or song loud enough to reach heaven.