Preheat oven to 300 degrees F.
Place bread on a large baking sheet. Bake in oven for 3-4 minutes to slightly dry out. Remove from oven. Set aside. Increase heat to 350 degrees F.
While the bread bakes, place butter, olive oil, brown sugar, and cinnamon in a small saucepan on medium heat. Cook stirring occasionally until butter melts and ingredients combine. Remove from heat and allow to cool a few minutes.
Drizzle butter mixture onto croutons making sure to cover as much surface area as possible. Mix, using hands to work the butter mixture into the croutons. Bake for 4 minutes. Remove from oven. Stir croutons to ensure even browning. Bake for an additional 4 minutes or until croutons are crispy. Cooking time may vary; make sure to check on it frequently. Remove and allow to cool on baking sheet.
Mix together cooled croutons, popcorn, chocolate chips, dried cherries, and pecans in a large mixing bowl. Serve. Store in an airtight container.