Leonardo first appears in the Teenage Mutant Ninja Turtles: Out of the Shadows movie skit, he is in the sewers along with Donatello waiting for Master Splinter. Once Splinter arrives Donatello asks for him to bless his fighting stick, which Splinter agrees to do. After Splinter finishes blessing the stick by shoving it down his eye, the two turtles make it out of the sewers. Leonardo calls out for the other two turtles, Michelangelo and Raffael but to no avail. As a gift for blessing Donatello's stick, they decide to buy him pizza, Donatello asks a lady walking by if she knew a pizza place number but she just walks away. After they remember a number, Leonardo calls the pizza place and orders two small pizzas, one with cheese and one with anchovy.
Forty minutes or so later the pizza arrives, instead of taking it to Master Splinter, they decide to eat it themselves since they were hungry. They get inside a sewer drain and start eating their pizzas, Donatello decides to throw Leonardo a piece of pizza, which angers him and causes a food/fieces fight. After the fight, Donatello decides to order two sandwiches, this time determined to give it to Splinter. Once the two sandwiches arrive, Donatello can't resist tasting one of them, despite Leonardo's attempt to stop him they both taste the sandwiches together. Once again Donatello throws a piece of sandwich at Leonardo, which causes another food/fieces fight.
After the fight they pack the remaining pizza and sandwich parts and head into the sewers. Once they arrive they find Master Splinter sleeping, after waking him up and force feeding him pizza and sandwich (along with worms Leonardo found), Splinter leaves the room.