Ready? Ok! (2008)

Charming and funny movie about a 10-year-old boy that wants to be a cheerleader, but his Catholic school won't let him because according to them only girls can be cheerleaders.

I really liked the way the character were portrayed as different and quirky, but it was not in a cartoony way.

According to IMDb.com :

In this poignant comedy, a single Mom struggles to understand her young son's obsession with dresses, dolls and girls' cheer-leading. With the recent death of her absent father, her wayward brother returns home, compelling them all to face themselves and what it truly means to be a "family"