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Brennan Huff (Will Ferrell) is a thirty-nine-year-old slacker who still lives at home with his mother, Nancy (Mary Steenburgen). When Nancy marries Robert (Richard Jenkins), Brennan discovers he's now related to his most hated enemy, Dale (John C. Reilly), another terminally unemployed loser. The two adversaries are forced to share a bedroom and slowly become the best of friends.