Little Black Sambo 

Contrary to popular belief, this is not just an insult.
Little Black Sambo was a series of children's books from the early- to mid-20th century. It centered around the titular character--a little African-American boy named Sambo--playing in the dirt, having a slice of watermelon, and doing many other things. As you may have guessed, this series is and was EXTREMELY racist. However, at the time it was considered very popular. If your parents or grandparents were children during the 50's or 60's, then ask them about Sambo, because chances are they'll remember him.
It can also be used as a derogatory term, which is explored to a greater length in the other definition of this word.

My grandmother gave me a book that she had as a little girl called Little Black Sambo. It was kind of racist...

Little Black Sambo by KilljoyRainbow July 9, 2014

Little Black Sambo 

Little Black Sambo is a dergoitory term for an african american whom one finds as weak, or physically inferior yet also of black heritage. Also was a small african child featured in a Looneytoons cartoon for when Looneytoons was still good.

Little black sambo is also one of the best comebacks to "Whiteboy" you aren't expected to say anything other than blackboy as a comeback but when you pull the LBS they have no idea what you say. Best used if followed by a British explorer accent to humor them to prevent an assault, similar to what Wild Bill said in the Green Mile.

Black guy: Hey, White boy!

White guy: Little black sambo.

Black guy: What???

White guy: (Strong english accent) Yes sir, yes sir! How do you do?!

Little Black Sambo by De Joden November 30, 2009