Chief Wiggum's on the spot when Homer becomes the latest victim of the Springfield Pickpocket.
This episode provides examples of:
- Actually Pretty Funny: Kent Brockman is visibly exasperated by the Hurricane of Puns his writers hand him for his report on the pickpocket, but he cracks a little when made to report on the capture by calling Fat Tony the "Wolf of Wallet Street."
- Deal with the Devil: While praying, Chief Wiggum asks God to overlook the fact he made a deal with the devil to become the Chief of Police.
- Epic Fail: While watching "Wheel of Fortune", Chief Wiggum sees the incomplete expression "_hief of Poli_e", the clue "Boy in Blue", and can't figure out on his own it means "Chief of Police".
- Even Evil Has Standards: Pickpocketing is the one crime Fat Tony is not willing to commit. His grandfather was about to get a heart transplant when the donor heart was pickpocketed, causing him to die the way no mob boss should - of natural causes.
- Frame-Up: Fat Tony is framed for the pickpocketing spree, and it's up to Chief Wiggum to clear his name.
- I'll Never Tell You What I'm Telling You!: Frankie the Squealer says he'll never tell Fat Tony it was Johnny Tightlips who set him up.
- Inadvertent Entrance Cue: Chief Wiggum states that to trap the pickpocket they need a huge ass that would provide an irresistible target. Enter Homer with his butt stuck to a park bench.
- Meaningful Name: Jimmy Kissass sucks up to Johnny Tightlips, Sonny Go-Along goes along with the power shift, Willy Whatever just shrugs about the whole thing, and Joey Can't-Read-The-Room can't figure out which side he should be on.
- Not Me This Time: Fat Tony is adamant that he wasn't the pickpocket.
- Rake Take: While escaping prison, Sideshow Bob is hit by a truck. Its cargo is made of rakes.
- Shout-Out:
- Kent Brockman's news report on the pickpocket has a picture of someone pickpocketing Wally with the caption "Where's Wallet?".
- Chief Wiggum is watching Wheel of Fortune when Lenora Carter shows up to take over the case.
- The scene of the Simpsons at the diner spoofs the infamous final scene of The Sopranos.
- The Starscream: Johnny Tightlips framed Fat Tony to take over his mob.
- Suspiciously Specific Denial: During the Feast of Saint Castellaneta, Mayor Quimby announces it's not a celebration of Columbus Day. It doesn't help his case that he's saying it while at the corner of streets named after the ships Columbus used during his first voyage to the New World.
- Tuckerisation: The Feast of Saint Castellaneta is named after Homer's VA Dan Castellaneta.
