Phenylpropanoid metabolism is one of the most important metabolisms in plants, yielding more than 8,000 metabolites contributing to plant development and plant–environment interplay. Phenylpropanoid metabolism materialized during the evolution of early freshwater algae that were initiating terrestrialization and land plants have evolved multiple branches of this pathway, which give rise to metabolites including lignin, fla-vonoids, lignans, phenylpropanoid esters, hy-droxycinnamic acid amides, and sporopollenin. Recent studies have revealed that many factors participate in the regulation of phenylpropanoid metabolism, and modulate phenylpropanoid ho-meostasis when plants undergo successive de-velopmental processes and are subjected to stressful environments. In this review, we sum-marize recent progress on elucidating the con-tribution of phenylpropanoid metabolism to the coordination of plant development and plant–environment interaction, and metabolic flux re-direction among diverse metabolic routes. In addition, our review focuses on the regulation of phenylpropanoid metabolism at the transcrip-tional, post-transcriptional, post-translational, and epigenetic levels, and in response to phyto-hormones and biotic and abiotic stresses.