Original air date: January 28, 2007
At a yard sale, Brian accidentally sells Rupert, Stewie's teddy bear, to a man who moves to Aspen, and the duo are on the road again to get the toy back. Meanwhile, Peter loses his driver's license after his latest stupid stunt, and Meg is forced to drive him and his immature friends everywhere.
This episode contains examples of:
- Animation Bump: Due to the original sequence in Anchors Aweigh having full animation, Stewie is animated much more elaborately than usual during the dance number (also because they needed to cover up Jerrynote , who dances with Gene Kelly in the actual film).
- Arson, Murder, and Jaywalking: Inverted. Joes starts off with reckless driving, disturbing the peace, and then finishes with rape.
- Artistic License Law: Joe says Peter committed rape against a driver because "she was a virgin whose hymen was busted by the airbag" during the car accident that Peter caused. Also, Joe hitting Peter just to get the license easily stands as assault, since Peter was not actually threatening Joe. Shows how much of a Dirty Cop Joe is. Also, the fact that Joe does nothing to stop the guys from distracting Meg while driving, and even joined in. Had Meg killed someone, or caused an accident (which did happen), Joe easily could have gotten fired.
- Bestiality Is Depraved: Stewie convinces Stanford to enter the skiing contest with Brian as the prize by telling him that if he puts peanut butter anywhere on his body, Brian will lick it off. Anywhere...
- Evil Laugh: Devil Stewie emits one.
- Eye Scream: Crone the Butler throws hot tea into Timmy's eyes on Stewie's orders.
- No-Holds-Barred Beatdown: Meg gives a brutal and graphic one to the driver who crashes into her.
- Rage Breaking Point: After all the crap she had to put up with driving Peter around, Meg snaps when the driver mentioned above yells at her.
- Roger Rabbit Effect: Stewie dances with Gene Kelly in a sequence from Anchors Aweigh.
- When Stewie and Brian's helicopter is about to crash, Brian looks over and imagines Stewie as the devil.
- Rupert's would-be funeral echoes Spock's actual one.
- The intro to My Black Son reuses gags from the intros to various sitcoms, including Laverne & Shirley, Who's the Boss?, and Bosom Buddies. Peter's co-star is also Emmanuel Lewis of Webster fame.
- So Proud of You: After Meg delivers a No-Holds-Barred Beatdown on the driver, Peter constantly praises her.
- Take That!:
- In a DVD-exclusive scene, Lois badmouths a DVD called Stymie Gruffin: The Untold Story (a rip-off of the Family Guy DVD-exclusive movie "Stewie Griffin: The Untold Stories"), deriding it as being "three episodes shown back-to-back" and that "FOX should be ashamed of themselves" (which gets cut off by two men in black suits dragging her away).
- Stanford's response to Stewie's offer of Brian licking peanut butter off his body is "Well, I did go to Choate...". In the DVD commentary, the writer who wrote that joke explains that the school he went to had a rivalry with Choate Rosemary Hall.
- Weird Currency: The helicopter can be rented for cash, check or a jaunty tune. The reasoning for that last one is that the rental agreement was drafted when musicals were still culturally relevant.
- Yank the Dog's Chain: Peter talks about what a great daughter he has right before Joe gives him back his license back. Meg expects Peter to immediately go back to dumping on her, but he says he'll only do so for appearance's sake and not really mean it.