The episode begins with Riley relaying a telephone call to Granddad:
- Riley: Oh, um, Granddad? There was something I was supposed to tell you. Uh, yeah... I think that uh... Aunt Cookie called and I think it was important.
Granddad: What? Did you write it down?
Riley: Naw, but uh, it was something about this dude named... Moe.
Granddad: Moe? You mean Moe Jackson?
Riley: Yeah, yeah, that's him! Uh, I think it was, uh, something about... Oh oh wait, I remember now. Yeah, something about him... dyin', or something."
Granddad calls Aunt Cookie and discovers that Moe died from failing to seek medical attention for priapism after taking erectile dysfunction pills. Rather than showing any sign of grief over the death of his friend, Granddad bursts into laughter and even starts dancing with joy. He decided to attend the funeral, however, when he learns that Moe left him something in his will.
Before leaving for Chicago (where Huey and Riley lived before being moving to Woodcrest), Huey reveals to Jazmine that he will be visiting his best friend, Cairo. This distresses Jazmine, who probably thought that she was Huey's best friend.
On the plane ride, Granddad tells the boys a story about Moe, and initiates a flashback to World War II. Granddad was "the best negro pilot of the war." Moe Jackson was his wingman. The flashback reveals that Moe is cocky, boisterous, and reckless. At one point during the flashback, Moe attempts to shoot down an enemy plane with his eyes closed. Unfortunately, this results in Granddad's plane being shot several times.
When Huey and Riley find Cairo, they are shocked to find that he has a new best friend, Dewey Abbado/Mamma-see,mamma-say,mamma-ma-cu-sah Jenkins. Dewey is a black revolutionary who mocks Huey for not being "down with the struggle" and for moving to "Whitecrest." Much to Huey's dismay, Cairo seems to have moved on.
Granddad finds out Moe left something for him, but in order to get it, Granddad must deliver the eulogy at Moe's funeral. Granddad is outraged at first, but is eventually talked into the idea by Aunt Cookie.
Moe's service is held on a party boat. At the service, Granddad is approached by an extremely ugly woman named Maybelline, but he screams and runs away after she talks to him. Huey becomes mad at Cairo for not being loyal, until Aunt Cookie tells Huey how upset Cairo was when Huey moved away. Granddad becomes more and more agitated as he learns that Moe has been taking credit for his accomplishments in the war, and also that Moe had called him "a motherfucker" only a few days before his death (contradicting his apologetic tone in the video). Granddad has trouble thinking of something to say, so he reads something written by Moe. "Everything I have in life, I owe to Moe Jackson. I'm not gay, but Moe was a very sexy man. We used to call him 'Moe Bitches.' I once saw Moe in his underwear, and it changed my life. I wish I had a father like Moe Jackson, Moe Jackson paid my rent over fifty times—OK this is bullshit!" He vents his true feelings about Moe to the entire audience, and storms off afterwards.
Later, Granddad finally reveals what caused the rift between him and Moe. Over 40 years ago, Moe had stolen his girlfriend, and Granddad had never forgiven him. Aunt Cookie scolds Granddad and reminds him that Granddad had never actually dated that girl. He asked for her number once and never called. However, Granddad retorts, saying that he was going to call her and she could have been "the one" and that Moe took that from him. Ironically, she also reveals that the same girl that caused the rift between them was Maybelline: the extremely ugly woman on the boat. She also tells him that even though Moe wasn't the best of friends, he wasn't the one who threw their friendship away, Granddad did. Granddad cannot believe how foolish he was, and how he had thrown away a friendship with Moe over something so stupid.
Meanwhile, Huey confronts Cairo about Dewey. Cairo takes Dewey's side, and openly mocks and insults Huey and Granddad. This causes a fight between the boys. Riley takes advantage of this opportunity, and takes off to fight Dewey. The fight ends abruptly when Granddad comes back in to make amends. He delivers a good speech, and forces Huey to "say something deep" at the end: "your pain is the breaking of the shell that encloses your understanding, it is the bitter potion by which the physician within you heals your sick-self therefore trust the physician and drink his remedy in silence and tranquility, Khalil Gibran".
After the funeral, when Granddad goes to pick his mystery item, he finds out that it was a jar of peanuts (Moe's final wish is for Granddad to "hold deez nuts!"). Moe had set everything up before his death so that he could have the last laugh on Granddad.
Before returning to Woodcrest, Huey goes to Cairo's house to apologize. It originally appears that Cairo has accepted his apology. However, Cairo reacts by headbutting Huey off of his front porch, leaving their relationship in tatters. When Huey returns to Woodcrest, he treats Jazmine somewhat neutral after realizing how important friendship is. Jazmine is seen poking fun at Huey's nose injury from the incident with Cairo. She jokingly says "I see your best friend likes to headbutt you in the face!"
The episode ends by revealing that Granddad actually kept the jar of peanuts. It is proudly displayed in his den alongside other memorabilia from his past exploits.
- The episode title is a double-entendre:
- In WWII, Moe was Robert's wingman (flight combat partner).
- Moe was also Robert's "wingman" in a social sense (a friend who deflects an ugly or undesirable woman's attention)
- The name of Granddad's plane in World War II was "Dorothy," the same name as his car. A piece of the plane can be seen in Granddad's den, along with other memorabilia. This is part of the running gag from both the strip and show where Granddad is in love with Dorothy Dandridge.
- The instrumental during Robert's flashback of Maybelline and Moe in the alley is from Madvillain's "Fancy Clown."
- Riley wears another suit to Moe's service similar to Tony Montana's suits in Scarface.
- When asked to "say something deep" at Moe's funeral, Huey quotes The Prophet by Khalil Gibran.
- The pictures on the wall of the party boat shows Moe with celebrities like Ray Charles, Michael Jackson and Muhammad Ali.
- The poem Dewey recites during Moe's funeral makes reference to Pookie in New Jack City, Tookie Williams, Arnold Schwarzenegger and Chewbacca from Star Wars.
- Moe and Robert are both flying P-51D Mustang fighters in World War II. The planes that attack them are Focke-Wulf Fw 190s.
- The background music for the dogfight scene is actually a remix of the opening theme.
- Moe and Granddad both have women painted on their Mustangs. WW2 era Tuskegee Airmen pilots were not allowed to paint on their planes as they were not given the same rights of a white man.
- Riley mockingly calls Dewey "Erykah Badu-ey," a dig at Dewey's African-influenced attire.
- Dewey butchers the Islamic greeting of "As-Salamu Alaykum" as "Salami, Eggs, and Bacon" illustrating he is a poseur who is clueless about the true meaning of what he preaches.
- Dewey questions Huey with "Where are your sandals? Where are your capris?" This refers to the 2003 track "The Yo Yo" by Little Brother where Phonte rhymes, "It's time to bring the emcees on/I'm sick of niggas lookin bitch trying to read poems/then try to battle me with sandals and capris on?/Come on dog...".
- Dewey's middle name is Abbado/Mamma-see,mamma-say,mamma-ma-cu-sah the later half being the scat bridge from Michael Jackson's track "Wanna Be Startin' Somethin'", itself an interpolation from Manu Dibango's hit Soul Makossa. (It was also later featured in Rihanna's hit Don't Stop the Music
- Dewey is a parody of the Black Arts Movement (link needed).
- After Cairo headbutts Huey, Riley was about to say "You got knocked the fuck out!" which was made famous by the movie Friday, which also starred John Witherspoon and Regina King, and which is referenced frequently in the series.
- The Moe subplot ends with the sentimental gift left by Moe to Robert Freeman, which are the jar of "DEEZ NUTZ!"