The episode starts off with Timmy, Chester, and A.J. sitting in the office of Dr. Bender's dentist room waiting to get their teeth fixed. When Wanda asks what going on, Timmy replies and says that they wanted to be in Chip Skylark's music video for his new hit song, My Shiny Teeth and Me. And that the only ones who are allowed are supposed to have shiny teeth to be in the video. Then Dr. Bender calls up Timmy and sends him into the dark dentist room. Timmy gets in the chair and Dr. Bender's preparing to rip his teeth out, but Timmy replies that his teeth aren't perfect by showing a picture of Chip Skylark's album, which gets Dr. Bender intrigued with Chip's teeth. Then Dr. Bender thinks of a plan to get Chip Skylark's teeth instead, so he and his son, Wendell, devise a "not so elaborate scheme" to "get medievil on Chip's mouth" by dressing as ninjas, sneaking in through the roof of Chip's apartment and yanking the teeth without disturbing anyone, which they managed to succeed.
Later that morning, Timmy is scared by a breaking news report, which reports that Chip Skylar's teeth are missing. Timmy immediately figures out that Bender had gone "medievil on Chip's mouth".
He wishes that Chip's teeth be returned to his mouth but Wanda replies that Tooth Magic falls under the jurisdiction of the Tooth Fairy, so they're powerless. Timmy decides he needs to get the Tooth Fairy to help.
Meanwhile, Chip's upcoming concert has rising pressure because of loss of teeth which affects his voice. Chip's concert is going to be cancelled but hastily, Chip's rival, Skip Sparkypants, is offered to be the new Chip Skylark. Chip tries to interject but without teeth his words are mixed into making Chet Ubetcha think that there's a boy stuck in a well and he reports he's gonna go get him out.
Timmy arrives at the shrine of the Tooth Fairy and asks if he could get an act of teeth retrieval done, but she refuses as she is busy and she can't go running off finding teeth, then Timmy says that the teeth belong to Chip Skylark. The Tooth Fairy gasps and reveals that his teeth are her finest work and most prized possessions. She gives Timmy the mission to get them from Bender with equipment such as the Toothbrush, the Floss Lasso of Truth, Steel Braces, and a Tiara of Disguise.
While Timmy goes after Bender and Wendell, Cosmo and Wanda try to stop Skip from getting ready for rehearsal. Cosmo and Wanda transform into dogs. While Skip changes and takes off his Sparkypants, Wanda sneaks up and snatches the Sparkypants, while Cosmo rips off Skip's underwear and runs away with it.
Timmy poofs at the dentist's office & confronts Dr. Bender & his son. Both Timmy & Bender then clash in a duel with both of them having their own gadgets. After defeating Bender, Timmy runs for the teeth but Bender breaks free and uses a vacuum to suck Timmy up. Timmy uses his Floss Lasso to grab the pillow the teeth were sitting on and hides under the pillow with the teeth and disappears by only leaving a quarter behind, much to Bender's shock.
The record company finds out the dilemma about Chip Shiny-Toothless and Skip Sparky-Pantless so they become desperate and tell the janitor he's the new Chip Skylark, but Timmy arrives and gives the teeth to Chip, who thanks Timmy & proceeds to shoot the music video.
After the video, Chip takes off his teeth and says something that is not understandable to Timmy. Timmy replies back with "You said a mouthful!", giving a shiny teeth smile as the episode ends.