Excelling in the tenor buffo repertoire, Reiss was particularly associated with the roles of David in Wagner's Die Meistersinger von Nürnberg and Mime in Der Ring des Nibelungen, two roles he sang in numerous houses internationally.
He appeared in several plays in Berlin and Strasbourg before deciding to pursue an operatic career under the encouragement of Bernhard Pollini and Ernestine Schumann-Heink.
He made his professional operatic debut in 1897 as Peter Ivanov in Lortzing's Zar und Zimmermann at Königsberg.
He made his first appearance at the company's house in New York City on December 23, 1901, as both the Shepherd and the Steersman in Wagner's Tristan und Isolde.
Most notably he sang in several world premiers with the company including: Nick in Puccini's La fanciulla del West, the Broom-maker in Humperdinck's Königskinder, Nial in Horatio Parker's Mona, the offstage male lover in Puccini's Il Tabarro, Richard II of England in Reginald de Koven's The Canterbury Pilgrims and Ragueneau in Walter Damrosch's Cyrano.