Despite being placed in the "roaring" twenties, I find that The Great Gatsby still has much to offer today's adolescents. The story of a man who goes from rags to riches all in effort of getting back the woman he loves is something that doesn't seem dated at all and the way it is told holds the readers interest throughout the novel. Nick is as interested in what's going on with Gatsby as I am and I think high school students might feel the same way. The only thing about teaching this book to students is it might require a quick introduction to how things were in the 1920's. Students would need to understand about the booming economy of the time, prohibition and how many became rich off of it illegally (such as Gatsby).
I think in comparison with Gatsby doing something illegal to make his millions, I would ask the class to write about how far they would go to get (or get back) someone/thing they loved. I think there's a good discussion in the accidental death of Myrtle and any other way it could have been resolved and how it would have affected the outcome of the story. I would want to spend some time with the class after finishing the novel and ask them questions such as, why were there so few people at Gatsby's funeral if he was so well-known? I'd also discuss that although Gatsby seemed to have everything he wanted in material possessions, what he desired most was Daisy and by not totally fulfilling his desire to get her back, did he actually ever achieve the American Dream?
For fun :]