The Chosen by Chaim Potok.

http://www.amazon.com/Chosen-Chaim-Potok/dp/0449213447

I generally agree that voluntary reading is better for the reader than assigned reading. And yet I must give my tenth grade English teacher in Wisconsin credit for assigning me to read The Chosen by Chaim Potok,

http://www.amazon.com/Chosen-Chaim-Potok/dp/0449213447

a wonderful book that acquainted me with the author, whose subsequent books are also well worth reading.

I think it is a replicated result among students of gifted students that they GAIN ground intellectually during the summer school vacation, because they pursue their own intellectual interests by independent reading and aren't slowed down by the school curriculum. At least, that was my experience in childhood.

A really good book for a teenager would be The Chosen by Chaim Potok,

http://www.amazon.com/Chosen-Chaim-Potok/dp/0449213447/

which I think I read at age fourteen. It's an excellent story about two very bright boys growing up in Brooklyn during World War II.

This is actually a very old tradition.

One notable example in popular culture is in Chaim Potok's novel "The Chosen"

http://www.amazon.com/Chosen-Chaim-Potok/dp/0449213447/ref=p...

From a review here:

http://litmed.med.nyu.edu/Annotation?action=view&annid=1...

"At Reb Saunders’s synagogue, he experiences Hasidism in practice, especially the practice whereby the Reb makes an intentional mistake in his sermon every week and challenges Danny to identify the mistake and elucidate it from the Talmud and commentaries."