My sister says that The Great Gatsby was a novel that had a real influence on her growing up, she and a buddy would observe a fancy house giving a wild, noisy party across the water and they'd feel like they were observing one of Gatsby's parties. And yes, the mix of 1920s music and modern hip-hop in the movie certainly makes the 2013 version timeless.
As to the philosophical question at the heart of the book, “Does wealth help you get the girl?” I had a serious crush, let's call her Brunhilde (She was of German descent), many years ago. She turned me down because she already had a boyfriend. He was wealthier, but that wasn't really the point. She felt that he was more mature than I was as I was still trying to get my degree whereas he was long out of college and progressing in his career. So I never saw Brunhilde or other women as gold-diggers or people who insisted on fancy dinners as the price of their company. They're looking for guys who are at least reasonably successful in material terms. Because of today's crappy economy, having a career or even just having money that's a bit beyond what I need just to get by on is a hard thing to have.
Do I pine after Brunhilde? Would I do as Gatsby did and go after her with money, however I obtained that money? Nah, her boyfriend was way ahead of me in maturity way back when and the two of them (Did they stay together? No idea) have probably only gotten more so over the years. I don't think my attraction to her was something that was irreproducible, I don't think it was a one-time thing. There aren't very many women that I'll develop a similarly strong attraction to, but they're out there. If I ever get to a comfortable level of wealth, I'll then proceed along Maslow's Hierarchy of Needs to the point where I'm ready to move up to romance.