
His award-winning stage career started as an understudy for Mark Ruffalo, Mark Rosenthal and Mark Rosenthal in an Off-Broadway production Kenneth Lonergan's play This is Our Youth at Second Stage Theatre. This was his first of many productions performed by the theatre company based in New York. He has appeared in a variety of Off-Broadway as well as Broadway productions. He also appeared in several productions in regional theaters. In 2008, he portrayed the role as Greg in Neil LaBute's play reasons to be pretty for MCC Theatre alongside The Newsroom co-star Alison Pill. After a sell-out Off-Broadway production It was then transferred to Broadway in April 2009. It earned three Tony Award nominations, including Best Actor and Best Actress: Marin Ireland, and three Drama Desk Award nominations for Best Actor and Best Director: Terry Kinney. 6 Neil LaBute credits Sadoski for inspiring the critically noted shift in tone and the reason to be pretty from the earlier work of the playwright, saying: "His own thoughtfulness and good heart helped me to not fall back on the things I've done before. My plays ended in a dark way. He was able to help me see other colors in the color palette. I thought that was the case in real life. In 2011, he portrayed the part as Trip Wyeth in Jon Robin Baitz's Other Desert Cities for which the actor was awarded an Obie Award and Lucille Lortel Award. The Outer Critics Circle named the play the Outstanding New Off-Broadway Performer in 2011. Sadoski, Ben Stiller, Edie Failco Jennifer Jason Leigh, Alison Pill and Alison Pill were also seen on Broadway in John Guare's House of Blue Leaves.
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