McMenamin made his rounds over the years playing bit parts on Law & Order, The Good Wife and Unforgettable, before appearing as Tony in the HBO miniseries Olive Kitteridge. He also played Sebastian from the sketch “Unpleasant Truths” during the first season of Inside Amy Schumer.

He earned his clout as thespian appearing on stage, with memorable turns as George in the 2009 revival off-Broadway revival of Our Town and appearing in the 2014 Broadway revival of Of Mice & Men opposite James Franco and Chris O’Down. Most recently he was cast as Charlie 'Donuts' Coates on Orange is the New Black.

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