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In the many years that I’ve closely followed the Academy Awards (starting in 2004 when Return of the King took home a record-tying 11 Oscars), I’ve only cared twice about who won Best Original Song. The most recent time was in 2012 when I desperately wanted to seeĀ Flight of the Conchords‘ Brett McKenzie win an Oscar for “Man or Muppet” from The Muppets. The first time was in 2006 where I would have likely started a riot if Three 6 Mafia hadn’t picked up the Oscar for their instant hip-hop classic “It’s Hard Out Here For a Pimp” from 2005’s Hustle & Flow. No matter what your other thoughts are about the film, there’s no denying that song’s place in the canon of great original movie tunes. Now, if only the rest of the film were as great as that song and the performances from Terrence Howard and Taraji P. Henson (Baby Boy).

There are few things more upsetting as a socially conscious film-goer than when you watch an obviously well-constructed and well-performed film but are also forced to recognize that there are some thematic… missteps in the work. And more than any of us would like to admit, there are a lot of great films that simply do not know how to handle their female characters. And Craig Brewer’s Hustle & Flow is one such film. As a portrait of desperation and the lengths we’ll go to achieve a dream even when our backs are against the wall, it’s a soaring success, and its social realism and gritty approach are greatly appreciated. But when every single woman in this film is simply a literal sex object and simultaneously used to massage the ego and self-esteem of the male star, that’s a problem of our male-centric film industry.

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2005’s Hustle & Flow is an underdog story in the mold of Rocky or Brassed Off! although without the cheesy triumphalism of the first or the social criticism of the second. Djay (Iron Man‘s Terrence Howard) is a philosophical and hardscrabble pimp who gets by tricking his snow bunny prostitute Nola (Taryn Manning) under Memphis underpasses. He’s got a stripper, Lex (Paula Jai Parker), with a major attitude problem and a son she doesn’t care for, and he’s got a pregnant “bottom bitch,” Shug (Taraji P. Henson), that can’t trick at the moment, but she loves and supports her pimp. Djay’s life is going nowhere fast, but he finds a chance to be somebody when he hears that rap superstar Skinny Black (Ludacris) will be visiting the bar Djay sells weed to for the Fourth of July.

Djay has one dream in life, beyond scrounging up the money he and his girls need to get buy, and that’s to be a hip-hop emcee. And after a chance meeting with an old high school friend, Key (Anthony Anderson), who pays the rent as a sound engineer for local church recordings, Djay thinks he finally has a shot at making his dreams come true and to get his mixtape into the hands of Skinny Black before his time runs out. And with a help from a local pianist and MPC machine enthusiast Shelby (DJ Qualls), Djay sets up a small recording studio in his house as he deals with the toils of keeping three different prostitutes happy under his roof. Will Djay find the muse he needs to make a genuine rap banger, and more importantly, will Skinny Black listen to it even if he does?

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Terrence Howard gives the performance his career in this film. Had Howard now turned down the supporting role of Rhodes in Iron Man 2 (because of salary disputes) and subsequently piss off all of the big producers in Hollywood, I suspect he could and should have been a big star. The 2005 Academy Awards was absurdly competitive for Best Actor (Philip Seymour Hoffman won for Capote and he was also competing against Heath Ledger in Brokeback Mountain), but Howard’s Academy Award-nominated turn in this film is one of the best of the aughts. Few performers have ever conveyed the feeling of having your back up against the wall and watching your life race past you as well as Howard does in this film. There’s a haunting intensity to the performance, and it’s a shame that he’s more or less disappeared from interesting projects in the 2010s.

And Baby Boy‘s Taraji P. Henson also gives her all to the thankless role of Shug. As I said, the women in this film are flat creations that are literal sex objects in that they’re all strippers/prostitutes (except for Anthony Anderson’s wife who has minimum screen time) and they have seemingly no real desires or character arcs of their own other than to support Djay in his journey. But despite that, Taraji P. Henson brings a wrenching emotional context to the character that certainly wasn’t in the script. She certainly at least deserved an Academy Award nomination in the Best Supporting Actress category at the Oscars that year. It’s a sign of a great performer when they are able to wrest an astounding performance from a mediocre character, and Taraji P. Henson does just that.

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The film’s problems with women can be summed up in one visual from the film. And, spoiler alert, I’m going to spoil something major about the film, but the movie’s nearly 10 years old now, so get over it. Djay is in prison for assaulting Skinny Black after he rejects him. Nola has slept with a radio DJ and gotten Djay’s single played on the radio. The song is called “Whoop That Trick” and a new mother Shug is singing along in full head-banging mode to a song that’s about beating on a hooker which is what she is. It’s like the movie isn’t even aware of the irony of the moment although at times I suspect it is because like Black Snake Moan, there’s a certain element of blaxploitation revivalism to Hustle & Flow. Regardless, the film’s usage of a prostitute singing along triumphantly to a song about beating on her own kind is the worst kind of male tunnel vision.

And those glaring oversights make for a frustrating viewing experience because Hustle & Flow is the kind of underdog film I can actually enjoy (because most are total garbage excepting the documentary Undefeated which manages to be a masterpiece). I sort of actively hate most non-Outkast/non-Killer Mike Southern hip-hop, but this film’s A-Town via Tennessee soundtrack is fantastic, and the film’s got that grainy 1970s cinematography that seamlessly matches the film’s storytelling style. And, as I’ve said, Terrence Howard’s firebrand performance holds the whole film together when it threatens to fall apart. Hustle & Flow falls just short of being a great film, but if you can look past its casual misogyny, it’s a superbly performed tale worth your time.

Final Score: B+