Jimmy Two-Teeth is a rat who lives in a wall in the office in Sam & Max Save the World and Sam & Max Beyond Time and Space. He is the husband of Mary Two-Teeth and the father of Timmy Two-Teeth. He appears in all episodes of Season One, but only really appears in the first and last episode of Season Two and is only briefly mentioned in The Penal Zone.
After his attempt to kidnap Sam & Max's phone in Culture Shock ends up with him being dropped out the window, he mostly avoids them to go about his own business. Still, their paths repeatedly cross in ways that end badly for him.
When the Maimtron 9000 breaks down at the start of Season Two, he uses the opportunity to rebuild it as a casino and take up residence there. In Ice Station Santa, Jimmy turns out to have an wife and son, and Sam & Max have to save their Christmas (or rather, prevent themselves from ruining it).
He was/is an excellent boxer (mainly because the ability of wielding a human-sized boxing glove). His full name is "James Tiberius Two-Teeth".
Jimmy is never seen in The Devil's Playhouse, but mentioned in The Penal Zone. Max hinted that Jimmy and other rats carried a plague, securing Max's re-election, and was bought off by Max to go into hiding.
Jimmy first appears in Culture Shock (also in the game's tutorial); in the introduction, he ransoms Sam and Max's phone for swiss cheese (which Sam and Max make by shooting the normal cheese with Sam's Gun). After demanding additional demands for the return of the phone and accidentally revealing he has a fear of heights, he is thrown out the window and forced to return the phone.
In Situation: Comedy he unsuccessfully attempts to steal shaving cream from Bosco's store. He then fails to buy Ted E. Bear's "famous meatball sandwhich" from Leonard Steakcharmer in The Mole, the Mob and the Meatball. He is briefly seen relaxing and swimming in the White House pool in Abe Lincoln Must Die!.
In Reality 2.0 he starts an arms dealership (though for what he claims to be suspected trickery, he denies Sam and Max service). He is later stuck into his canon and shot at Sybil by Sam and Max; he also is revealed to have a gold coin (once again stolen by Sam and Max) in Reality 2.0. He later becomes the target of Philo Pennyworth's "pull the rats out of the hats" trick in Bright Side of the Moon. Sam and Max help Philo enough so that he can successfully snatch Jimmy away; Sam and Max, now the owners of Jimmy, used him to help defeat Max's Gluttony.
In the pilot episode, Jimmy inhabits the destroyed Maimtron 9000 and sets it up as a boxing ring. With the help of Boxing Betty; a remote-controlled boxing doll; Sam and Max defeat Jimmy and these 2 other rats and claim the prize. Jimmy stands at the edge of a building starting to consider suicide.
However, Sam and Max travel to the past in order to save a Christmas in the past for The Spirits of Christmas; it is revealed that they are saving Jimmy Two-Teeth, and his family (consisting of his wife Mary Two-Teeth & son Timmy Two-Teeth)'s Christmas past. They re-witness Leonard Steakcharmer's kidnapping and see that since Jimmy's family can't make the deal, they can't make money and that Timmy Two-Teeth's terminal tourette syndrome can't be fixed. Mary harshly criticizes Jimmy for being unable to box or make money and tells him that he is unnecessarily blaming Sam and Max for everything. Sam and Max trap Mary in the world's simplest maze then give her to the present-day Jimmy Two-Teeth (still thinking about suicide) and when given the comfort of his wife, he decides to not commit suicide. It should be noted that this means Mary Two-Teeth did not exist from this moment to Ice Station Santa.
He also appeared with basically the same role in Sam & Max Nearly Save Christmas.
After being of little to no role in Moai Better Blues, Night of the Raving Dead & Chariots of the Dogs Jimmy appears in What's new, Beelzebub? still managing the Maimtron 9000 (now a firework show for the kid rats). Sam and Max then made the Maimtron stand up and all the rats in it fell out; including Jimmy's son Timmy. Sam and Max's goal of using the robot to attain the soul token so they could take the train to Hell worked, though Jimmy was in a very worried state as "falling from great heights" is fatal to someone with Timmy's condition.
As Timmy begins to pass away next to The C.O.P.S. and his father, Jimmy seems to have somewhat a change of heart and admits that he is a sinful person and his innocent son doesn't deserve this death. Nevertheless, Sam and Max switch Timmy and Jimmy's "sin folders" in hell; this convinces a harsh Death to send Timmy to hell in the same one of Grandpa Stinky's. Due to his abundant cursing, the show he and Stinky are watching (Girl Stinky being successful) gets cancelled by the Master of Censoring; freeing him and Grandpa Stinky. While Timmy stays with the Maimtron 9000, Jimmy ends up losing bets at Abraham Lincoln's bachelor party.
He is briefly mentioned in The Penal Zone in an optional conversation that Sam can have by talking to Max -- he and his pals apparently left the building after support from an anonymous benefactor.
- He once join a group called the "Skinbodies" which are a gang of rats who started to steal shaving cream from Bosco to shave their entire bodies (minus the heads).
- He's either unskilled in electronics or just a little inept, as he may have misinterprated what his friend, Benny Three-Knees instructed him to do in Bright Side of the Moon: Rig Sam & Max's answering machine to shock one of them when he played the third message. Instead, he left a third message, pretending to be Sybil in an attempt to do so.
- In Abe Lincoln Must Die!, Max mentions how Jimmy is a lobbyist for affordable health care for the aged and underprivileged.