Howard founded The Flying Karamazov Brothers in 1974, while studying Biology at the University of California at Santa Cruz. From early performances opening for Commedia plays, they went on to Renaissance Faires, street performing, and folk, rock and comedy clubs before breaking into legitimate theatres. The Flying Karamazov Brothers have performed in major venues all over the world, including the Goodman Theater in Chicago, New York's Lincoln Center and the Kennedy Center in Washington DC, and have enjoyed six runs on Broadway, as well as innumerable television performances (including an appearance on Seinfeld), and major roles in the film The Jewel of the Nile. They played with symphony orchestras including The National Symphony, The Cleveland Symphony, the St. Louis Symphony, and the Chicago Symphony, and appeared twice at Carnegie Hall.
Howard plays trombone, euphonium, percussion and ukelele, as well as a host of Renaissance instruments including sackbut, rauschpfeife, recorder and krummhorn. He is the inventor of "musical juggling," and has performed on a variety of juggling instruments of his own invention, including an electronic juggling suit, backdrums and the six-octave Floor Organ (developed with MIT's MediaLab). He studied liturgical singing with the late Cantor Alan Michaelson, and leads High Holy Day Torah services at congregation Havurah Shalom in Portland, Oregon. He sings baritone.