I really didn't care for Hustle & Flow: I thought the movie bought into the macho gangster rap bullshit of its pimp-turned-artist hero. I agreed with David Edelstein that "[w]hat's missing in this self-proclaimed story of redemption... is something other than a fairy-tale finale. It's the sense that the filmmaker understands the consequences of exploiting women even if his protagonist doesn't."
But its Oscar-winning song "It's Hard Out Here for a Pimp" did get me thinking: just how hard is pimping? And how does its "hardness" compare to other professions, illicit or otherwise? For instance, is pimping more or less difficult than selling crack? Producing and distributing child p*rnography? Making a living as an armed robber? As a confidence man? And is pimping harder or easier than driving a truck? Teaching high school? Training guard dogs? Being a heart surgeon?
I think this would be an interesting line of inquiry for someone who's good at statistics and measurements and stuff (like Steven Levitt, who did such interesting research on why so many drug dealers live with their moms).
On a related note, someone who's into arts and culture commentary could look into the question of why some activities/professions are romanticized in song (pimps, crack dealers, truck drivers) and some aren't (dog trainers, confidence artists, child p*rnographers). It probably has something to do with what the kids back in grad school liked to call "class and gender issues".