Karen Goodman and Kirk Simon produce and direct the half-hour series that debuted in 2010.
Musician McFerrin's episode will be the first to air on Feb. 12. Exact air dates for episodes featuring LuPone and Guare were not announced, however, HBO expects to roll them out in March and April.
Portions of LuPone's Gypsy In My Soul concert engagement in Madison, WI, were filmed for inclusion in the segment featuring the two-time Tony-winning Evita and Gypsy star.
Guare's plays include The House of Blue Leaves, Six Degrees of Separation, A Free Man of Color, Landscape of the Body, Four Baboons Adoring the Sun and more. He is the Tony-winning book writer of Two Gentleman of Verona.
Previous installments of "Masterclass" have included Edward Albee, Liv Ullman, Placido Domingo, Jacques D'Amboise and Olafur Alliason. The episodes feature artists working directly with a select group of talented students.