First appearance: “Bart’s Friend Falls in Love” (Season 3, Episode 23)
Notable appearance: “A Milhouse Divided” (Season 8, Episode 6)
Voiced by: Hank Azaria

The life of Kirk Van Houten could easily be called an American tragedy: He’s a balding, middle-aged man who gets divorced, fired, and has his musical dreams crushed all within the span of a 30 minute episode, the formidable “A Milhouse Divided.” Yet in the twisted world of The Simpsons, Kirk's failings are designed specifically for our amusement, and witnessing his misery has become one of the show’s greatest pleasures over the years.

Kirk is best known as the father of Milhouse Van Houten, Bart’s best friend. Milhouse is anything but underrated, but for our money Kirk is the real standout of the family. He's a former major player down at Southern Cracker, until his life falls apart and he's forced to sleep in a race-car bed in a derelict bachelor pad with the rest of the town’s sad-sack single men. Since then, Kirk has evolved into the show’s resident punching bag.