"two And A Half Men" Pie Hole, Herb(2008) -

(Season 6, Episode 2) is a fan-favorite installment of Two and a Half Men that first aired on September 29, 2008. It is widely remembered for its absurd look at fraternal power dynamics and the unlikely bonding between Charlie Harper and Judith’s second husband, Herb Melnick. The $38 Debt: A Fragile Brotherhood

While Alan is crashing at their place, Herb (Ryan Stiles) visits Charlie’s house to pick up Alan’s things. Instead of a quick errand, the two hit it off, bonding over margaritas and model trains. "Two and a Half Men" Pie Hole, Herb(2008)

In one of the show's classic physical comedy sequences, a disoriented Alan sleepily wanders into his former marital bedroom and gets into bed with Judith. (Season 6, Episode 2) is a fan-favorite installment

Fed up with Alan's pettiness, Charlie kicks him out and changes the locks. The "Herb" Connection Instead of a quick errand, the two hit

Alan attempts to siphon gas from Charlie’s car to recoup the value. Charlie catches him after smelling the gas on Alan's breath and humorously threatens him with a lighter until he confesses.

The episode kicks off when Alan Harper (Jon Cryer) lends Charlie (Charlie Sheen) a mere . While a small sum for the wealthy Charlie, the debt becomes a point of obsession for the chronically broke Alan.