Henry H. Pleas, III has sung under conductors Helmut Rilling, Christoph Eschenbach, James Conlon, Bruno Bartoletti, and Roger Norrington. Principal roles include the title role in Offenbach's Tales of Hoffman,Turriddu in Cavalleria Rusticana, and Don Jose in Carmen. Mr. Pleas has also appeared as soloist in presentations of Beethoven’s Missa Solemnis, Handel's Messiah, Mozart’s Requiem, Vaughan Williams’s Hodie and the extended cantata, Done Made my Vow by american composer Adolphus Hailstork with the Grand Rapids Symphony.

Henry was a finalist in the 2008 Lotte Lehman CyberSing competition, past winner of the Maderia award for Excellence in Music at Brown University, and a past participant in the Lyric Opera Center for American Artists. He performed both Schubert’s Schwanengesang and Die Winterreise at the Pianoforte Foundation’s Schubertiade and other venues.

Henry Pleas' performances with Chamber Opera Chicago was described by ChicagoClassicalReview.com as "riveting".