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Keith Olbermann makes his much anticipated (by him) appearance on Family Guy in the aptly named episode "It Takes A Village Idiot (and I Married One)". Rumor has it the name of Olbermann's character is an homage, in part, to the Managing Editor of Olbermann Watch.
When Lois runs for mayor of Quahog to stop illegal dumping by the evil Quahog Oil Company, she isn't the front-runner until she "dumbs down" her political views by repeating "9/11" over and over. Once in office, she's corrupted by the power and starts accepting bribes so that she can buy herself expensive trinkets. Meanwhile, Peter's enjoying being the "first lady" and all of the perks that go along with it. Olbermann plays Bob Groosebeard, the head of Quahog Oil. Keith's character co-opts Lois by buying her a fur coat. Lois has a change of heart about her political career.