In 2008, he appeared in two Christmas movies, in the Hallmark Channel movie "The Most Wonderful Time of the Year" as a retired cop who plays matchmaker between his niece and a drifter he befriends, and in "Merry Christmas, Drake & Josh" as the judge who orders Drake and Josh to give a young girl "the best Christmas ever" or be sent to jail. In 2009, Winkler provided the voice of Willard Deutschebog, a suicidal German teacher, in the Fox comedy series, "Sit Down, Shut Up."