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Sam Richardson. Sam is an alum of The Second City Mainstage, and has been in \\u201cWe\\u2019re the Millers,\\u201d \\u201cHorrible Bosses 2,\\u201d and the upcoming \\u201cSpy.\\u201d Sam was a recurring in \\u201cThe Office,\\u201d and is currently a regular on HBO\\u2019s \\u201cVeep.\\u201d