"Have you ever had a cherrychanga? Ooh! Sorry, that was a question." - Pinkie Pie
Pinkie Pie invents the cherrychanga in The Last Roundup. She only mentions mashed-up cherries in a deep-fried tortilla, so I'd call the cream filling optional. I do think it adds more flavor depth (read: tastes delicious), and makes the recipe akin to that of strawberry cheesecake chimichangas.
Incidentally, you know who also likes saying funny words like 'chimichanga'? Deadpool. Wonder if those two would ever get along...
Scoop cream cheese filling along the middle third of each tortilla, leaving an inch or so on each side.
Spoon mashed cherries on top, again along the center.
Next, fold the two sides of each tortilla toward the center and then roll the tortilla up like a burrito (see below pictures). (If you need to, you can use toothpicks to keep the whole thing together.)
Combine the remaining 1/4 cup sugar with the cinnamon in a shallow bowl and set it aside. Line a large plate with paper towels.
Add 3 inches of oil to a large, deep saucepan, leaving a minimum of 2 inches from the top of the oil to the top of the saucepan. Heat the oil over medium-high heat until it reaches 360ºF on a deep-fry thermometer (or when the tortilla hisses when you set it in oil).
Fry each cherrychanga until golden brown and crispy (about 3 minutes each side).