Does the carpet match the drapes?
The commissioner is looking into an underground operation at Ted E. Bear Mafia's-Free Playland and Casino, but the mole he sent in has suddenly gone quiet. To find the mole, Sam & Max must infiltrate the operation and become members of the Toy Mafia themselves by getting a stolen sandwich back, making a hit on a witness, and "convincing" a local shopkeeper to sell the Toy Mafia's merchandise.Tropes:
- Becoming the Mask: Harry Moleman, the mole sent undercover into the Toy Mafia, has fully embraced his new role as Don Ted E. Bear.
- A Bloody Mess: Done deliberately when Sam and Max are sent by the Toy Mafia to assassinate Sybil. In order to fake her death, Sam steals her coffee mug, fills it with ketchup, and shoots it so that the resulting red mess gets all over Sybil's shirt.
- Broken Record: The dealer at Ted E. Bear's just says "Wanna play cards?" whenever you talk to him.
- Casino Episode: Sam and Max infiltrate a casino-themed family playland.
- Cheese-Eating Surrender Monkeys: Bosco's persona as "Jean-Francois Sissypants". This was toned down in the remastered version but still has him loudly proclaiming he surrenders when the Toy Mafioso enters.
- Comical Overreacting: When Sam fakes shooting Max, the latter launches into a lengthy, drawn-out death monologue that goes on so long, Harry admits he was about to make Sam shoot Max again.
- Even Bad Men Love Their Mamas: Leonard Steakcharmer. So much so that Sam and Max decided to torture him with a stream of Yo Momma jokes.
- Gratuitous French: Bosco as "Jean-Francois" has a habit of inserting random French words and phrases into his speech.
- Hoist by His Own Petard: You defeat the head of the Toy Mafia by turning one of his own hypnotizing teddy bears against him, which leads to him getting stuck in the machinery and blowing up the factory.
- Homemade Inventions: Bosco's "Miniature Listening Device," AKA a Literal Surveillance Bug.
- Hypocrite: Leonard cheats at gambling by relying on a reflection across the room to see the card on his head, yet when you turn his cheating method against him and beat him at his own game, his first instinct is to immediately accuse you of cheating the moment he loses everything.
- The Mole: The commissioner sent a mole into the Toy Mafia, but they've gone silent and Sam and Max are sent to become ones themselves to rescue them. Turns out, not only are they an actual Mole(man), but also switched sides, become the newest Don in the process.
- Monster of the Week: Don Ted E. Bear and the Toy Mafia.
- Most Definitely Not a Villain: The Toy Mafiosi running the casino.
- New Job as the Plot Demands: This time, Sybil has become a professional trial witness. This naturally gets her targeted by the Toy Mafia.
- Not What I Signed on For: Sybil really regrets what being a "professional trial witness" means once the Toy Mafia tries to assassinate her.
- Oblivious Guilt Slinging: The trope namer, in fact, when Sybil confides in Sam and Max that she feels they are the only people she can trust. Little does she know they've been tasked by the Toy Mafia with killing her...Max: She should try guilt slinging as her next career choice.
- Or My Name Isn't...: Bosco insists that the Toy Mafia won't be selling their merchandise in his store, or his name isn't Jean-Francois Sissypants!note Max immediately points out that that isn't his name.Bosco: Shh! Zey don't know zat!
- Paper-Thin Disguise: Bosco again. This time, he's donned a black beret and is speaking in a French accent, using the alias "Jean-Francois Sissypants, the cowardly French anarchist" (changed to "Jean-Francois Bande-a-part, the new-wave French anarchist" in the Remastered version).
- Rapid-Fire Interrupting: Partway into the "Do you have any...?" exchange, Bosco starts pre-emptively saying "Non!" before Sam can finish his question.Sam: Do you have any...
Bosco: Non!
Max: How'd you know what he was gonna-
Bosco: Non!
(next option)
Sam: Do you-
Bosco: Non!
(next option)
Sam: Do-
Bosco: Non!
(next option)
Sam: (after a Beat) Do you-
Bosco: Non!
(next option, there is a long pause as Sam stares at Bosco, and Bosco stares back)
Sam: Do you-
Bosco: Non! - Red Alert: Trapping the Don in his bear-making machine causes the machinery to overload, leading to this exchange:Max: Sam, I forget, which color is the one that means I can't take my bath and body scrub with me?
Sam: (pointing at the alarm) That one! RUN! - Sergeant Rock: Bosco's "listening device" is a bug with a tough military-guy voice who claims to have served in 'Nam.
- Shoot Your Mate: When Sam and Max finally confront the Don, he attempts to hypnotize them, and in order to make sure it's worked, he orders Sam to shoot Max. Sam obliges, albeit using a cap gun stolen from Leonard, and Max launches into an overly dramatic death monologue that lasts so long the Don considers having Sam shoot Max again.
- Shout-Out: Sam's attempts to guess the password to the back-room of Ted E. Bear's include "swordfish", "Rosebud", "Bring Me the Head of Alfredo Garcia", "I've come to Grandma's funeral", "Who's on first?", and "I am the walrus". The actual password is "Leave the guns, take the cannoli".
- Spanner in the Works: The Puzzle Boss is defeated by trapping him in his own teddy-bear making machinery.
- Suck E. Cheese's: Ted E. Bear's is a casino crossed with a Chuck E. Cheese's, serving as an obvious front for the Toy Mafia.
- Suspiciously Specific Denial: Ted E. Bear's Mafia-Free Playland and Casino is most definitely not run by the Toy Mafia. They even have a theme song about how there's no actual mobsters around.Ted E. Bear's is oodles of fun
Slots and sandwiches and poker and guns
And look, no mobsters, nary a one
Just you and me and Ted E. Bear! - Tastes Like Chicken: Max eats the webcam the Toy Mafia were using to spy on Sybil, and remarks it tastes like chicken.
- The Three Trials: To join the mafia, Sam and Max must kill Sybil (or rather, fake her death), deliver a Teddy bear to Bosco's, and take back Ted E.Bear's original meatball sandwich from a thief.
- The Vietnam Vet: The roach you use to find out the Toy Mafia's secret password claims to have served in 'Nam, and remarks with disgust about the senseless slaughter of ladybugs and larvae.
