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Leland is a nerdy boy in Greg's neighborhood. He lives next door to Rowley, and he is his babysitter. Leland taught Greg and Rowley how to play "Magick and Monsters", which is a game based on several real-life games including Dungeons and Dragons. Rodrick later told Greg that Leland's the "biggest nerd is his school." In the "Winter Talent Show," Leland did a ventriloquist act and won the grand prize.