Boys can do anything, including cry
General Kid resources: Resources For Kids
It's bad to make boys think they always need to be strong, never cry, and rescue everyone.
What are some good tales of boys who like dolls, cry, get saved, or in other words are real children?
Games
The siblings in Brothers: A Tale of Two Sons
Monroe, The Unfinished Swan
The Boy in A Bird Story
Ness, Earthbound
Maxwell, Scribblenauts
Books
Sparkle Boy https://www.goodreads.com/book/show/33113622-sparkle-boy
Joseph Delaney's series. Percy Jackson series which would fit both girl and boy list.
Hatchet
Robin McKinley's _Dragonhaven_
Frindle. Tangerine. Holes
Fievel in "An American Tail".