He has acted on the stage, most notably in several productions of Kenneth Lonergan's play "This Is Our Youth". In 2015, he portrayed Rye Gerhardt in season 2 of the FX series "Fargo". He portrays Roman Roy in the HBO series "Succession", for which he received nominations for the Golden Globe Award for Best Supporting Actor – Series, Miniseries or Television Film in 2019 and 2020 and the Primetime Emmy Award for Outstanding Supporting Actor in a Drama Series in 2020.