Best Supporting Actor

The Iambic Pentameter Award for Best Actor in a Supporting Role in a Shakespeare Play is an award presented annually by the Iambic Pentameter Club. It is given to a performer who has delivered an outstanding performance in a supporting role in a play that opened that year. The award is traditionally presented by the incumbent Creative Director of Iambic Pentameter. It is the only competitive acting award given by Iambic Pentameter that is not divided by gender.

While there is typically only one Iambic Pentameter production per year, the plays often feature an ensemble cast with multiple strong supporting roles, giving multiple actors the opportunity to win the award.

The most recent winner of the award is Penny DellaPelle, who won for her role as Don John in Much Ado About Nothing (2021).