Henry H. Pleas, III was born in Chicago, Illinois, and educated in Chicago area schools. He attended Brown University, and at graduation, received the school's Madeira Prize for Excellence in Music. After Brown, he continued music studies attending the University of Illinois at Urbana-Champaign and later, Northwestern University where he received a Master of Music degree.

Mr. Pleas has appeared as leading tenor in many operatic productions, including work as soloist for Lyric Opera of Chicago, Opera Grand Rapids, Skylight Opera Theater and Chicago Opera Theater. His roles have included the title role in Tales of Hoffmann, Rodolfo in La Boheme, Tamino in the Magic Flute, and Turridu in Cavalleria Rusticana, and Don Jose in Carmen. In orchestral performance he has appeared as principle tenor soloist in the Beethoven Missa Solemnis, Mozart Requiem, Handel's Messiah, Mendelssohn's Elijah, Haydn's Creation, Britten's St. Nicholas, Stravinsky's Pulcinella, Vaughan William's Hodie and Adolphus Hailstork's "Done Made my Vow".

He lived for several years in Germany, working, improving his use of the German language and coming to understand a little better a culture that gave birth to a wealth of important poets, composers and great singers. He is a frequent recitalist; to date he has performed Schubert's Winterreis e and Schwanengesang , Liszt's Petrarch Sonnets , and a good deal of the song repertoire from Benjamin Britten. He frequently collaborates with Steinway Artist, Chris Garofalo with several performance of his song cycle, In the Circle of the Seasons, composed to the poetry of Unitarian Universalist poet and minister, Edward Searl.