In Benjamin Bear’s Naughtiest Night Ever! Mama and Papa Bear plan to go out for the evening and leave the cubs with a babysitter. Benjamin Bernard Blackbear, though, wants his parents to stay home and play with him and his siblings. He figures that if he is naughty enough, he can urge or at least encourage the babysitter to flee from the house at the end of the evening, and never babysit them again.
So, Benjamin hatches a plan to achieve this end, recruiting his 3 year-old twin siblings to help in the naughty plot. Benjamin learns his babysitter for this fateful night is not only a novice babysitter, but that this is her very first time watching anyone’s offspring!
Chaos ensues once the Blackbear parents have gone out and Benjamin is let loose on this poor unsuspecting teen grizzly. After the parents return home, they find their home rather wrecked, and the mess has Benjamin’s name written all over it.
The mess is so great that Mama and Papa Blackbear are rendered speechless. Their pledge to not spank their cubs is sorely tested, but the Bear parents dole out natural consequences instead, and gradually mercy. Benjamin after all, is their only beloved seven year-old son.