Loogie was a sixth grade student at Jerome Horwitz Elementary School when George Beard and Harold Hutchins were in Kindergarten. He was a member Kipper Krupp's gang, and along with Kipper, Finkenstein and Bugg, they bullied the kindergartners by taking their lunch money and giving them wedgies. He also attended wrestling classes with the rest of Kippers gang.
Captain Underpants and the Terrifying Return of Tippy Tinkletrousers
Loogie and the rest of Kipper's gang are first seen bullying Harold along with Billy Bill, but George notices them and after Kipper and his gang leave the scene, he gets revenge on Billy Bill. George and Harold become friends. Later, they go back to the school where Kipper and his gang are. George then takes out his tie and whips them, causing the bullies to retreat to a nearby dumpster. Then after that incident, George and Harold decide to take down Kipper and his goons for good so they start pulling pranks on Kipper. These include putting dresses and friendship bracelet kits in his locker, tricking them into eating ghost chili pizza, and filling the kids' lockers with shaving cream.
One stormy night, George and Harold left Kipper and his gang a comic book telling them the spooky tale of Wedgie Magee, successfully convincing them that they were under a curse. After hearing a voice that was apparently Wedgie Magee (a toy walkie-talkie propped up against the locker) they fled to the bathroom where they saw George dressed up in some stilts and a large pair of pants pulled over him, scared them to the extent that they ran home. From that day forward, Kipper and his gang were nice to kindergarteners.
But when Tippy Tinkletrousers goes back to the moment Kipper and his gang fled the school, he scared them to the extent that they went completely mad! So Kipper, Loogie, Finkenstein and Bugg all where sent to the goof house. Mr. Krupp was blamed for their madness and was fired. Tippy then went forward in time to the present and found that the villains from books 1, 2, 3 and 5 had destroyed the Earth completely because there was no Mr. Krupp to be hypnotized into Captain Underpants, and therefore nobody that could defeat them.
Captain Underpants and the Revolting Revenge of the Radioactive Robo Boxers
Due to the Earth being destroyed, Tippy went back in time to the moment Kipper and his gang fled the school, he shrunk his old self and froze Kipper, Loogie, Finkenstein and Bugg before moving out of the way and unfreezing them and going forward in time now that everything was set right.