A look back at 50 Cent’s industry-shaking song ‘How to Rob’

On Aug. 10, 1999, 50 Cent, real name Curtis Jackson, released his first major label single. The song “How To Rob” was featured on the soundtrack of the film In Too Deep, which starred Omar Epps and LL Cool J. It was 50 Cent’s first notable appearance since his initial appearance on Onyx’s “React” in 1998.

But “How to Rob” was anything but your average debut single. The record featured a young artist who was largely unknown outside the New York mixtape circuit explaining how he would rob famous music industry figures from Jay-Z and Timbaland to Boyz II Men and Keith Sweat.

“At first, I thought 50 had a death wish,” Kid Capri, the Grammy Award-winning producer and DJ, told Andscape. “I thought it was a brilliant idea. It was marketing within itself because it attracted the wow factor. I remember people saying, ‘This dude, 50 is crazy.’ ”

It’s a fair assessment. The bars he delivered on the song were a mix of tongue-in-cheek humor (“I had Busta and the whole Flipmode on the floor/He asked me if I had enough I told him gimme some mo”) and what sounded like actual threats of violence.

He threatened to kidnap Lil’ Kim and hold her hostage unless P. Diddy “dance your a– down to the nearest ATM.” Missy Elliott and producer Timbaland were teased about their weight. Husband and wife singers Bobby Brown and Whitney Houston were potential stickup victims, too (“I’m about to stick Bobby for some of that Whitney money”). 50 Cent hilariously threatened to rob Cash Money Records star Juvenile for all his jewelry, including his gold teeth. 50 Cent’s lyrics poked at an endless array of rappers, singers, producers and DJs.

“He said a lot of crazy bars on the record,” Kid Capri recalled. “I think the record didn’t cause no problem because he went at everybody, so people didn’t take it personally. It was a perfect way to get attention.”

The violence on wax never turned into violence in real life, thankfully. However, the release of “How to Rob” gave 50 Cent his first taste of industry notoriety and ruffled feathers at the highest levels of the music business.

An early version of the song made its way around the Columbia Records office, the label 50 Cent was signed to at the time. Singer Mariah Carey, then 50 Cent’s labelmate, heard the record and allegedly threatened to take legal action against her own label if the lyrics about her weren’t removed from the song. The offending line — “I’ll manhandle Mariah like ‘B—-, get on the ground/You ain’t with Tommy no more, who gon’ protect you now?” — targeted the singer and her former husband Tommy Mottola, then chairman and CEO of Sony Music Entertainment, the parent company of Columbia. The line about Carey and Mottola was removed from the official single, but the original version can still be found on YouTube.

And then there is Jay-Z.

On “How to Rob,” 50 Cent’s lyrics hinted at something sinister: “What Jigga just sold, like four milli? He got something to live for/don’t want a n—a putting four through that Bentley Coupe door.”

In August 1999, Jay-Z was already a multiplatinum artist with Billboard-topping singles such as “Hard Knock Life.” Many wondered whether the Roc-A-Fella boss would respond. And respond he did in a very public way.

At Summer Jam in 1999, Jay-Z famously went on stage and rapped the lyrics, “I’m about a dollar — what the f— is 50 cents?“ A reworked line also appeared on “It’s Hot (Some Like It Hot)” off Jay-Z’s In My Lifetime Vol. 3 album, which was released in December 1999.

It was the most public rebuttal to 50 Cent’s controversial record. Still, as Jay-Z explained later in a radio interview, he enjoyed “How to Rob” and told 50 Cent so backstage at Summer Jam before he proceeded to diss him in front of thousands.

” ‘How To Rob’ did its job. It got people talking,” said Kid Capri.

It was one thing to listen to and enjoy “How To Rob” from afar, but it was another thing to be mentioned in the song. Mister Cee, the longtime New York DJ who discovered the Notorious B.I.G., received a lyrical jab on the track. 50 Cent rapped, “I’m hungry for real / I’m about to stick Mister Cee, that n—a still eating off BIG first LP,” which referred to Mister Cee being an executive producer on the multiplatinum hip-hop classic Ready to Die.

“I was a little bit scared when the record dropped,” Mister Cee recalled. “He was talking about people should stick me up because I was making money. I was wondering if people would come up to me, and that’s exactly what happened. Not to rob me, but reciting the line and asking me if I was still making money off Big’s LP.” 

Following the release of “How To Rob,” 50 Cent’s buzz increased across the music industry, and Columbia Records accelerated the recording of his debut album, Power of the Dollar.

However, the project would go unreleased. Columbia dropped 50 Cent shortly after the rapper was shot nine times while sitting in a car outside his grandmother’s house in Queens, New York. 50 Cent operated independently and built a buzz via the mixtape circuit. Eventually, rappers Eminem and Dr. Dre noticed his momentum and decided to take a chance by signing him to their Aftermath Records label. The move eventually led to the 2003 release of Get Rich or Die Tryin, the best-selling album of 2003, and 12 million copies were sold worldwide by the end of the year.

But one needed to be in New York City when “How To Rob” dropped to truly understand its impact on the streets and hip-hop’s mixtape culture. DJ Doo Wop, one of the architects of New York’s mixtape scene, recalled his reaction upon hearing the record. 

“In the ’90s, the highlight of my mixtapes was the freestyle segment. I didn’t just have the average local rappers on my tapes. I had the hottest artists rapping on my tapes,” Doo Wop said. “And when ‘How to Rob’ came out, I knew I needed 50 on my tape.

“He comes into my studio to rap,” Doo Wop continued, “and one of the first lines that comes out of his mouth was ‘I’m the next best thing since Biggie and Pac.’ ”

Brash. Fearless. Funny. 50 Cent’s innate ability to be likable while simultaneously seeming like he was living on the edge of life and death took the Queens emcee to unimaginable heights, including selling more than 30 million albums worldwide. “How To Rob” was the catalyst for a career spanning decades, cementing 50 Cent’s legacy as a hip-hop legend.

“It was a statement where he was saying, I’m coming in here whether y’all like it or not,” Mister Cee said.