Season 5, episode 14 “Homermandias”

In a flashback, Homer and Ralph Wiggum conduct their first meth cook. Homer calls a pregnant Marge with an excuse for not being home, and she suggests the name Hootie McBoob for their baby.

Milhouse is wounded following the shootout with Hans Moleman’s brotherhood, and The Squeaky Voiced Teen is dead, but Moleman and his gang are unscathed. Moleman prepares to kill Milhouse but Homer begs Moleman to spare him, offering his entire $20 peanut fund in exchange. Milhouse chides Homer for not realizing Moleman is going to kill him anyway; Moleman kills Milhouse, and Homer collapses to the ground in despair.

The gang discovers Homer’s speakeasy barrels; they take six, but at Moe Szylak’s request, they leave the seventh for Homer, then bury Milhouse and The Squeaky Voiced Teen in place of the barrels. Homer identifies Ralph Wiggum’s hiding place and demands Moleman carry out the hit Homer requested. Moe Szylak suggests taking Ralph captive first to learn what he revealed to Milhouse and Squeaky Voiced Teen. Homer consents, and spitefully tells Ralph that he allowed Wiggle Puppy to die. The gang detains Ralph in a cell, then forces him to cook meth for them.

Homer’s car runs out of fuel so he rolls his barrel through the desert until he purchases a truck from the nearest homeowner. Unaware of what transpired in the desert, Luann Van Houten informs Marge that Milhouse has arrested Homer. She demands that Marge relinquish the false confession video implicating Milhouse and tell Lisa the truth. Marge informs Lisa about Homer’s Beer Baron business, and she tells her she is as bad as Homer for going along. Homer arrives home and frantically tries to get Marge and the kids to leave with him. Marge realizes Milhouse has been killed and threatens Homer with a kitchen knife. During a fight, Bart tackles his father to the ground and Lisa calls the police. Homer kidnaps Maggie and flees.

Luann and the police arrive at the Simpsons' home. Rex Banner taps the phone when Homer calls. Homer attempts to establish Marge’s innocence by falsely claiming he built his Beer Baron business alone and berating her for not helping him. Homer confirms Milhouse’s death, ends the call, and leaves Maggie at a fire station with ‘742 Evergreen Terrace’ written on a note. The next morning, Homer meets Gil Gunderson, Lionel Hutz's new-identity contact, who drives away with Homer and the barrel.