3. Kirk Van Houten20th Century Fox40-something Kirk Van Houten is the middle management mid-life crisis nightmare. Everything falls apart for Milhouses weekend Dad when Luann demands a divorce from the pathetic figure in A Milhouse Divided at the Simpsons dinner party. Unsurprisingly Luann gets custardy of Milhouse and Kirk is forced to leave the family home and move into a pokey bachelors apartment where he sleeps in a pitiful racing car bed. While Kirks love life goes absolutely nowhere, he must look on as his ex-wife starts a relationship with the strapping Pyro an American Gladiator who is the polar opposite of the doughy Kirk. Watching your former wife and the mother of your only child frolicking with a man who could literally tear you limb-from-limb must be a very sobering experience. The elder Van Houten becomes so desperate to win Luann back that he even attempts to cut off his own foot in Large Marge. He is eventually sacked from his managerial role in the Cracker factor and finds re-employment as the assistant to a flier distributor. It should come as no surprise that Kirks depressing post-divorce life drives him to alcoholism and even attempted suicide.