Craig Brewer will never forget when he tried to write a rap song in the script that would become “Hustle & Flow.”



“I would try to put in some flow, just a paragraph to get it going, and then I realized...” Brewer paused. “It just felt wack.”



Thankfully, Brewer stopped himself, and instead gave us one of the most unlikely Academy Award wins in the show's history.

Brewer’s “Hustle & Flow” came out of nowhere in 2005 to become one of the most memorable indies of the year. The journey of a Memphis pimp named Djay (Terrence Howard) who aspires to become a rapper quickly became a must-see for hip-hop fans and cinephiles alike.

"Hustle & Flow." Paramount The movie was championed by “Boyz n the Hood” director John Singleton, who came on as a producer, and launched the careers of Howard and Taraji P. Henson (who plays a pregnant prostitute with an incredible voice). It also paved the way for "Dirty South" rap, which was just beginning to hit the mainstream, giving the film an underdog sensibility as it made its way to the Oscars in 2006.

This year’s Oscars marks the 10th anniversary of when the film’s lead track, “It’s Hard Out Here for a Pimp,” written by the Memphis group Three 6 Mafia, won the award for best song — the first time a rap group ever won the prize.

Business Insider talked to some of the people behind the song and movie to uncover how it was created and what its win, which was considered a shock at the time, means now.

Searching for the music

Around the time of Craig Brewer’s failed attempt to come up with rap lyrics, in the early 2000s, he was making the rounds in Hollywood, script in hand, trying to find financing for “Hustle & Flow.” Brewer always planned to showcase Memphis rap in the movie, but as he recalled to BI, in those early meetings, the executives would throw out more commercial names like Nelly, Dr. Dre, and Snoop Dogg.

“I think they knew about five rap songs,” Brewer said of the Hollywood suits. “They would say, ‘You need to get this guy Nelly,’ and they would also say Sisqó — I think 'The Thong Song' was out at that time.”

Thankfully, Brewer found a savior in Singleton, who came on as a producer and financier in 2003, and also had knowledge of the Memphis rap scene, as he’d featured a Three 6 Mafia song in his 2001 movie “Baby Boy.”

(L-R) Craig Brewer, "Hustle & Flow" producer Stephanie Allain, and John Singleton. Paramount Even before production began, Brewer and Singleton were planning out the songs for the movie, especially one showcasing Djay’s life.

“John kept saying, ‘We need a song that shows how difficult it is to be a pimp,’” Brewer said. “But we also wanted to articulate the absurdity of that, because it’s an outrageous idea. I mean, really, how hard is their life?”

Brewer drove that home in the scene in which Djay comes up with lyrics for “It's Hard Out Here for a Pimp,” while walking with his friend Key (Anthony Anderson), who is struggling to carry an air conditioner. Djay never offers to help.

Brewer and Singleton were still in search of the key song for the movie when they paid Three 6 Mafia member Juicy J for the song “Pop It for Some Paper.” The two also signed on another Memphis rapper, Al Kapone, to write a few more tracks for the movie, including one performed by Djay on screen, "Whoop That Trick."

Then during preproduction, Brewer and Singleton visited Three 6 Mafia’s studio, Hypnotize Minds Camp, to check on how Howard was doing recording “Pop It for Some Paper” (which Howard would end up doing a cappella in the movie). And there, music history was made.

Creating the song

Three 6 Mafia were already legends in the Memphis rap scene before "Hustle & Flow." Members Juicy J, DJ Paul, and Lord Infamous (who died in 2013) had their own record company in the early 1990s, and sold their early albums in and around Memphis as either Backyard Posse or Triple 6 Mafia. They later signed with Sony, changed their name to Three 6 Mafia, and expanded the group, which at the time of "Hustle & Flow" included rappers Frayser Boy and Crunchy Black.

Brewer had met Juicy J in Memphis years earlier, and when Howard agreed to play Djay, the writer-director had the actor meet the rapper, which led to a mixed encounter.

Three 6 Mafia. Stefano Paltera/AP “I got a call from Juicy, and I knew Terrence was hanging out with Three 6 Mafia, so I asked how it was going, and he said, 'Man, he left.' I was like, 'What do you mean he left?'" Brewer remembers.

Brewer tracked down Howard back at his hotel and found he wasn't getting a good vibe hanging out with the group at Hypnotize Minds Camp.

“You know, their studio is right next to the jail,” Singleton points out.

"I realized what was happening," Brewer said. "Terrence was standing in front of Memphis rappers and he was going to have to play one. That's a real intimidating experience."

Brewer went back to Juicy J and explained the pressure Terrence was under. Juicy J understood what he had to do. That evening, he showed up at Howard's hotel with a bottle of Cristal and no entourage.

"The next time I talked to Terrence, he had the Memphis accent down. He transformed," Brewer said. "That was all because of Juicy. That's producing — get your talent comfortable."

Terrence Howard as Djay in "Hustle & Flow." Paramount

Weeks later, when Brewer and Singleton arrived for the “Pop It for Some Paper” recording, Juicy J was in another producing mode: hustling.

“Juicy felt the deal that John gave him for ‘Pop It for Some Paper’ wasn’t right,” Brewer said.

When everyone got settled in the studio, Juicy J said to Singleton, “It’s really too bad you’re not f-----g with us on that pimp song,” referring to the song Brewer and Singleton were searching for that would highlight Djay’s struggle.

“Well, you know, business,” Singleton answered.

“Yeah, but listen to this business,” Juicy J said, then hit the space bar of his laptop to reveal the beat he and DJ Paul came up with for what would become “It's Hard Out Here for a Pimp.”

“And Juicy pulls out a napkin where he wrote the hook,” Brewer explains. “And he tells us, ‘Yeah, I was going to have the pregnant ho sing:

‘You know it’s hard out here for a pimp /

When he tryin' to get this money for the rent /

For the Cadillacs and gas money spent /

Will have a whole lot of b-----s jumpin' ship.'"

Brewer said Singleton’s face lit up with excitement.

“But you gotta get deeper in the pocket a little more John,” Juicy J told Singleton. “Because I’m not gonna give this to you for free.”

That’s when Singleton went into producer mode. He had Henson, who was also in the studio, go into another booth to record the hook Juicy just sang. And then Singleton and Brewer sat with Fayser Boy to talk about the focus of the song.

“The first thing that popped in my head was ‘it’s hard out here for a pimp,’” Frayser Boy told BI. “John looked at me and goes, ‘What did you say?’ And I said, ‘It’s hard out here for a pimp, that needs to be the name of the song,’ and he just looked at me and said, ‘That’s it!’”

“So I go in this other room with Frayser,” Brewer said. “He cuts up a cigar, dumps out the tobacco, rolls a blunt, and starts writing what later we know to be an Academy Award-winning song.”

"We got this term in Memphis called pimpin', something that's old-school, and it already had that pimpin' flavor, so it was easy to write," Frayser Boy said. "It took me only 30 minutes to write both verses."

Going out for air, Brewer came across Singleton and Juicy J chatting in the lobby.

“They are talking about what club they are going to that night, but then John would look at his Sidekick,” Brewer said, “and he would type something, and then Juicy’s would ding. ‘Oh, that’s what you want, huh?’ Juicy would say out loud.”

Brewer realized the two were negotiating the terms of “It's Hard Out Here for a Pimp” via their phones.

“So from the moment that Juicy played that beat on what would be 'It's Hard Out Here for a Pimp,' the song was written, produced, recorded, and negotiated maybe within three to four hours,” Brewer said.

A historic Oscar night with behind-the-scenes uneasiness

The conventional thinking before the 2006 Oscars was laid out by a Billboard story: “Most predict Dolly Parton’s ‘Travelin’ Thru’ from ‘Transamerica’ will claim best song...”

The biggest musician to sing in a movie usually walks away with the statue (think Céline Dion for "Titanic"). But Brewer and Singleton felt they had the ace card this year: a song that was the movie.

“Whatever people think about rap music, when they watch these characters struggle to make a song, then it becomes the audience's song, and that's what happened with 'It's Hard Out Here for a Pimp,'" Brewer said. "When I heard it got nominated, I was like, 'We're going to win it.'"



The Academy wanted to utilize the connection between movie and music on Oscar night by having Howard and Henson perform the song in character. Howard (who was also nominated for best actor) declined. Singleton says his decision was influenced by others.

“Terrence didn't want to because people in the black film community didn't want him to perform as a pimp on the Oscars," Singleton said. "I really wanted Terrence to perform, and years later Terrence regrets not doing it."

Singleton declines to mention the people who objected to Howard performing as a pimp, saying they're some of the same people boycotting this year's Oscars over the nominees' lack of diversity.

(L-R) Three 6 Mafia members DJ Paul, Juicy J, Frayser Boy, Crunchy Black arriving at the Oscars. Kevork Djansezian/AP But Howard opened the door for Three 6 Mafia to be the first rap group to ever perform at the Oscars, doing the song alongside Henson.

“They started flying us back and forth for meetings and getting us prepared. We had to do choreography," Frayser Boy said. "We were just happy to be there."

Three 6 Mafia performing at the Oscars. Mark J. Terrill/AP Though the evening had better musical numbers than most Oscars ceremonies — a somber number by Kathleen "Bird" York for "Crash" and Parton bringing the audience back to church — "Hustle & Flow" was easily the highlight.

The title "It's Hard Out Here for a Pimp" was in a large glowing sign at the top of the stage, part of which was made up to look like the room Djay used to record the song in the movie. Three 6 Mafia, who had shown up in suits, were now in their sunglasses, chain, and baggy clothes, while Henson sang the hook in a beautiful white dress (replacing the word "b-----s" with "witches"). Backup dancers played pimps and prostitutes, including one made to look like Djay.

"I'm in the audience sitting there watching this crazy music number and part of me was like, 'Geez, I'm totally responsible for this,'" Brewer said. "I was also thinking, somewhere there's an Oscar party going on and people are thinking, 'What the hell is this?'"

“I had these big shades on during the performance because I was so nervous," Frayser Boy said. "But then I saw Jamie Foxx in the front row singing the words to the song that I wrote. Man, that meant everything to me."

Three 6 Mafia were rushed to the side of the stage after the performance, as Queen Latifah came to the podium to announce the winner for best song.

“I had tunnel vision," Frayser Boy said. "Everything was moving in slow motion, and it was like me and Queen Latifah connected eyes when she opened the envelope and before she even announced the winner, I knew she was going to say 'It's Hard Out Here for a Pimp.'"

Even before acceptance speeches could go viral on social mdia, the win was an instant classic in awards history. Juicy J, DJ Paul, and Frayser Boy rattled off names to thank, with a shout-out to George Clooney in the front row. Host Jon Stewart came on afterward and said, “That's how you accept an Oscar.”

Frayser Boy recalls that the group was the toast of every Oscars after-party.

"The first party was the Vanity Fair party, and we had the Oscar in our hands, and we walked into the party and all eyes were on us," he said. "I met anyone who's anyone that night and they all wanted to meet me. The only thing I regret is I didn't take pictures."

Juicy J and DJ Paul showing off their Oscars. Kevin Winter/Getty But Brewer’s favorite memory was the one told to him by his friends back in Memphis.

“Every Oscar night, this place called the Pink Palace in Memphis holds this Oscar party where old-school Memphis shows up. And when I mean old-school Memphis, I mean old white people," he said. "When 'It's Hard Out for a Pimp' won, they leaped out of their seats and cheered and screamed. Our win meant a lot to the city. That's where the racial lines fall — the unity behind the city itself."

The 'Pimp' legacy continues

Ten years after the Oscar win, "It's Hard Out Here for a Pimp" is part of the popular vernacular. “I’ve had preachers come up to me and say, 'It's hard out here for a preacher,'” Brewer said.

And recently we finally saw Howard and Henson perform the song that made them famous as a duo, when the two "Empire" stars went on Spike's "Lip Sync Battle."

As the years passed, Three 6 Mafia changed members and their name (to Da Mafia 6ix). Juicy J went solo and Frayser Boy moved to another label. But looking back, Fayser Boy still feels like that Oscars night was all a dream.

“It's a benefit that never runs out because people believe in your vision," he said. "You pretty much got the trophy to show what you can do."

(L-R) Craig Brewer, Juicy J, Frayser Boy, and DJ Paul receiving the key to the city in Memphis following the Oscars. Mike Brown/Getty And where does he keep his Oscar?

“I donated it to the Memphis Rock 'n' Soul Museum, so it's there now for a couple of years," he said. "I like people to see mine. That's something in a million years I didn't think I could do, and that title in front of my name — Oscar winner — is everything to me, because it means I really did something. Where I'm from, Memphis, Tennessee, a lot of people don't come out. A lot of my friends are dead or in jail. It's just a blessing to be sitting here and to show that you can come from the hood and still make it."