Windgassen was born in Lennep (now part of Remscheid) in the Prussian Rhine Province.
Following the wishes of his upstanding middle-class parents, he took up a respectable career in the German navy.
Further engagements took him to Bremen, Hamburg, and the Court Theatre in Kassel, where he met the coloratura soprano Vali von der Osten, whom he married in 1916.
Beginning in 1919 he increasingly specialised in Heldentenor roles and became a renowned interpreter of Richard Wagner.
He gave his farewell concert in Stuttgart in 1949, featuring works by Richard Strauss, Gustav Mahler, and Hugo Wolf among others; his son, Wolfgang Windgassen, later a celebrated Heldentenor in his own right, also took part.