Toby Flenderson takes the stage by storm and is nominated for an Obie for his heartfelt portrayal of Willy Loman in the Off-Broadway revival of "Death of a Salesman" in 2011.

He loses to Seann William Scott for his role in "The Sweet Agony of Defeat" and the following year becomes a 'stage father' when he accompanies his thirteen year old daughter Sasha in a touring production of "The Sound of Music" where she plays Louisa Von Trapp.

He understudies several Nazis in the production, and receives a card from Michael Scott reading simply "I knew it!!!!"

During the tour in Los Angeles, he meets actress Reese Witherspoon and the two begin dating. They marry in 2014; it is the second marriage for both.