Hank is preparing to have Bobby use the whetstone that Hank bought the day Bobby was born to sharpen the mower blades. Hank tells Bobby that if he proves himself, he can use the mower. Before either event can happen, however, Bobby places the whetstone on his pile of video games. The whetstone falls off and shatters. As a result, Hank has Bobby rakes leaves until the whetstone is paid off. But after Hank discovers Bobby is using the rake for a comedy routine, he promptly grounds him. He later catches Bobby in his room sniffing various items including his Game Boy. Hank then heads over to Cotton's to help repair various items when Cotton floats the idea of sending Bobby to his old military academy - Fort Berk. After Peggy reluctantly agrees to send Bobby, Cotton and Hank give Bobby a cadet's uniform, and accompany him to the base. Cotton and Bobby enter the base (Cotton refuses to let Hank enter, as he doesn't think Hank is good enough), and Cotton warns Bobby that he's in for a rough boot camp. However, Bobby finds out that the hazing has become less brutal, and they actually serve edible food in the cafeteria, in contrast to Cotton's days at the Academy. At supper, Cotton speculates that Bobby is sleeping in animal droppings, and a hysterical Peggy drags Hank to the Academy to check on Bobby's well-being.
As it turns out, Bobby is doing very well, and the Academy even allows Hank and Peggy to sit in on an art class, where Hank makes a bowl. After Hank and Peggy notify Cotton of how things have changed at the Academy, he is angry, and he heads over to Fort Berk and promptly convinces the head of the Board of Trustees to fire the commanding officer after discovering that his childhood "hole" is now serving as a storage space for Christmas supplies. He temporarily takes over the Academy after promising to pay parents with interest. Extremely hopeful of Bobby's potential, Cotton subjects Bobby to various challenging tasks, including picking up leaves with a fork, eating a pile of rotten backwash, and sitting on an ice block. When all of these plans don't go Cotton's way, he is enraged. He throws Bobby into "the hole", a form of solitary confinement on the Fort's grounds. Word of this gets to Cotton's wife Didi, who informs a panicked Hank. Hank speeds over to the Fort and releases Bobby out of "the hole."
The boy is unharmed and unbroken by his days in the hole. Cotton and Hank have a little talk about how Bobby is like mush, it can't be broken and it can't be built up, but it has the edge. However, after noticing how unfazed Bobby is when playing with the other cadets, Cotton then laughs and states that if Bobby had been in a POW camp, the Japanese would have gone crazy and would have given up on WWII after three days with him. Cotton tells Hank that he wished he could see the old Fort Berk back in Cotton's day. Hank realizes that with all the talk, his father never gave him permission to speak, and Cotton, realizing this as a subordination, orders him to drop and give him twenty. Hank obliges happily. The fellow cadets ask Bobby how he managed to hang on, and he informs them that he was inspired by graffiti which indicated that Cotton Hill lasted in "the hole" for two days, while Bobby lasted for three.
- Hank Hill
- Peggy Hill
- Bobby Hill
- Cotton Hill
- Fort Berk principal
- Didi Hill
- Crafts teacher
- Army cadets
- The episode's title is a parody of the film An Officer and a Gentleman.
- This episode reveals that Hank was willing to go to military academy when he was a child; however, Cotton didn't let him because he thought Hank wouldn't have what it takes.
- At the end of the episode, some graffiti is shown on the wall, listing Cotton and Bobby's names as well as the number of days, reading "Cotton Hill Two Days" and "Bobby Hill Three Days." The individual graffiti logs may have been added just before Bobby and Cotton went into "the hole."
- This is the only episode in the series in which neither Bill, Boomhauer, nor Dale appear, making Hank, Peggy and Bobby the only characters to appear in every episode.
- The controller Bobby was playing video games with is similar to the design of a Nintendo 64 controller, although the pile of games near him seem to be on discs (the N64 used cartridges which came in bulkier, rectangular cardboard boxes).
- This episode shows that Bobby has strong willpower and that his spirit isn't easily broken.
- Cotton: "What the?! You made a bowl?"