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Robbing Celebs and Shooting the Mayor: The Story Behind the Two Most Controversial Rap Songs of 1999

A young 50 Cent needed a hit—so he wrote a song about mugging famous rappers. Meanwhile, the group Screwball recorded a track about killing Rudy Giuliani. Here’s how two controversial rap upstarts were thwarted in an era that wasn’t ready for the drama.

Alycea Tinoyan

Welcome to 1999 Music Week, a celebration of one of the most interesting, vivid, varied music years ever. Join us as we count down the best singles and albums of the year, remember the days of scrubs and the girls who wear Abercrombie & Fitch, and argue about which albums stood above the rest.


It was the spring of 1999, and 50 Cent was a desperate man. He had just returned from recording in Bearsville, a leafy hamlet in Woodstock, New York, with Tone and Poke of the Trackmasters, the production duo responsible for Nas’s “If I Ruled the World,” LL Cool J’s “Hey Lover,” and Will Smith’s nine-times platinum Big Willie Style.

The 23-year-old Queens rapper, who was about to sign with the Trackmasters’ imprint on Columbia Records, had completed approximately 40 songs while upstate, yet was still trapped in the hip-hop equivalent of development hell. Not one of those songs was regarded as a potential single. 50 had no buzz. Furthermore, his debut album, Power of the Dollar, had no release date. “We knew that we needed a record that would make a big impact on radio,” Poke says today.

50 had an idea. He’d been a fan of The Notorious B.I.G.’s “Just Playing (Dreams),” better known as “Dreams of Fucking an R&B Bitch,” on which Biggie fantasized about sexing every R&B honey from Mary J. Blige to Chante Moore. What if, 50 thought, he remade “Dreams” but with a twist? What if he did a song about robbing famous artists?

50 fleshed out the concept with Trackmasters consigliere Rich Nice, an A&R executive at Columbia, before rapping the song for Tone and Poke. Once it was approved, 50 recorded his vocals at the Hit Factory.

The song’s message—a starving rapper stealing from the rich and powerful—required a delicate touch, and a comedic chorus was added to diffuse the tension. Rich Nice summoned Deric “D-Dot” Angelettie, the Bad Boy producer moonlighting as The Madd Rapper. “This ain’t serious,” D-Dot rapped, “being broke can make you delirious.”

See, the hook was saying, this was all a joke. No need to get upset. Angelettie knew better. “Yo,” he said to Rich Nice toward the end of the recording session, “you know this is going to make a lot of noise, right?”

“How to Rob” made a lot of noise even before the public heard it; fellow Columbia Records artist Mariah Carey allegedly threatened to sue her own label for defamation after learning of the record. (An early version of the song contained the line: “I’ll manhandle Mariah like ‘Bitch, get on the ground / You ain’t with Tommy no more, who gon’ protect you now?’”). 50 altered it following pressure from then–Columbia chairman Donnie Ienner, and Carey’s ex-husband, then–Sony chairman CEO Tommy Mottola. A crack about the rapper AZ was also removed.

Still, like Biggie, 50 named names: Foxy Brown, Jay-Z, DMX, Puff, Big Pun, Wu-Tang, and more all got got on “How to Rob.” (Sample lyric: “I’ll rob Pun without a gun, snatch his piece then run / This nigga weigh 400 pounds, how he gonna catch me, son?”) 50 intended to cause a stir. More importantly though, he wanted radio to pay attention, and he got his wish: “How to Rob” exploded onto Hot 97 in the spring of 1999. 50 had his radio hit—or so he thought.

The story of “How to Rob,” and “Who Shot Rudy?,” a provocative song from the group Screwball released around the same time, is a cautionary tale about breaking new artists and attempts to go viral in 1999. How both records took off—before they eventually crashed and burned—reveals how much has changed in the rap industry over the last 20 years, and how much remains the same.

“They were nuts. We were all nuts, but they were extra nuts.”

That’s Mike Heron describing Screwball, the Queensbridge rap crew he signed to his independent label, Hydra Records, in the mid-1990s. Now vice president of A&R at Shady Records, Heron was a former juvenile delinquent with an impressive record collection when he formed Hydra with fellow Queens native Jerry Famolari in 1994. Hydra had its offices in Long Island City, a stone’s throw away from the Queensbridge Houses, a breeding ground for rappers (e.g., MC Shan, Tragedy, Mobb Deep, and Nas) since hip hop’s inception in the late 1970s, and the home of Screwball; the group took its name from a fallen friend, Louis “Screwball” Chandler.

“We were in Queens. They were in Queens. It’s that simple,” Heron says. “We were all from the streets. I don’t think it’s ever going to happen like that again. The water isn’t the same anymore. … All of these connections are deeply entrenched in street culture.”

Heron sounds wistful for a lost era, a time when ties were formed in the streets and then carried over into the music industry. 50 Cent’s big break was similarly quaint. He rapped for then–Sony senior executive vice president Cory Rooney, a friend of a mutual neighborhood friend, outside a Queens barbershop. Rooney then introduced 50, whose affiliation with Run-DMC’s Jam Master Jay had run its course, to the Trackmasters.

The four members of Screwball—Blaq Poet, Hostyle, Kyron, and KL—also held some experience in the rap game. Poet was best known for the 1987 KRS-One diss “Beat You Down,” while KL and Kyron, who recorded as the duo Kamikaze, had a minor underground hit with the Marley Marl–produced “On the Real,” featuring fellow QB MC’s Nas and Cormega.

Like all formidable rap crews, each artist in Screwball brought something different to the table. Heron compares Poet to DMX, another hardscrabble MC who utilized simple rap patterns but rapped with sincere conviction. KL was known for his forceful delivery and raspy voice. Hostyle was nicknamed the “One-Eyed Maniac,” due to the fact that he lost an eye when a cop tasered him and was considered, um, somewhat eccentric. A prolific writer, Kyron was the group’s secret weapon. “One of the most gifted rappers I’ve ever worked with,” Heron says.

After a series of independent singles, Screwball’s fortunes turned following a meeting between Heron and Eddie O’Loughlin, the founder of Next Plateau, the indie label that broke Salt-N-Pepa in the late 1980s. Heron and Eddie O, now at Tommy Boy, had a long conversation during which they talked about recording equipment and Heron’s record collection. Eventually, they discussed Screwball.

“It felt like 10 minutes, but [the meeting] went for two hours. This was the first time I had a long conversation with a white dude who wasn’t a special ed. teacher, a police officer, or my stepdad,” Heron says. “At this point Eddie looks at me and is like, ‘I’m signing this group.’ I don’t know how this music shit works at this point. I’m like, ‘Don’t you want to hear the music? He’s like, ‘Nope.’ I’m like, ‘Don’t you want to meet the group? It’s four motherfuckers and Poet looks like fucking Leon Spinks and they’re fucking crazy. ... All right, cool. I’ll have [my lawyer] call.’” The meeting ended with O’Loughlin predicting that Heron would become a great A&R. “Bro, I have goosebumps thinking of that shit,” says Heron. “Eddie O’Loughlin changed my life.”

Heron envisioned Screwball as a mini Wu-Tang with each member releasing solo projects between group albums—but on a much smaller scale. Screwball were not for the mainstream. After all, their lead single “F.A.Y.B.A.N.”—an acronym for “Fuck All You Bitch-Ass Niggas”—featured the group shouting the mantra on the chorus. It was unfit for commercial radio even though, again, it was the freaking lead single!

Screwball’s debut, Y2K: The Album, initially slated for release in late summer 1999, would be their launchpad to modest success. Featuring production from Heron and boom bap deities DJ Premier and Pete Rock, Y2K: The Album was a solid, not quite spectacular, slab of late-’90s New York street rap. Keeping to Heron’s plan, each member of Screwball got their chance to shine. KL’s energy steals the show on the Premier-produced “Seen It All.” Hostyle wielded his nimble flow on “H-O-S-T-Y-L-E.” “F.A.Y.B.A.N.” is a showcase for Poet. As for Kyron, his moment occurred on a song titled “Who Shot Rudy?”

By the summer of 1999, the relationship between New York City mayor Rudy Giuliani and the city’s black and brown population was one of volatile contempt. A former associate attorney general in the Reagan administration, Giuliani was elected in November 1993 on a vow to reduce the crime rate. He adhered to the “Broken Windows” theory of policing, in which the enforcement of misdemeanors like graffiti, public drinking, and fare evasion are strictly enforced. Broken Windows advocates believe that the zero-tolerance policy toward minor crimes prevents more serious crimes. There’s no definitive connection between the two.

Giuliani’s two terms as mayor were marked by several high-profile police brutality incidents: Victims Abner Louima, Amadou Diallo, Ernest Sayon, and Patrick Dorismond became household names as well as shorthand for the lack of empathy and accountability that emanated from City Hall following each tragedy. New Yorkers still feel passionately about Giuliani, who left office on January 1, 2002. “Fuck Rudy Giuliani forever,” Heron tells me.

And so when Screwball dropped a record titled “Who Shot Rudy?” into this environment it was bound to erupt. “Motherfuckers were like, ‘Yoooo, hold up. ‘Who Shot Rudy?,’” Poet says with a laugh. “It was funny to me, but it turned out to be serious business. It got the attention of a lot of motherfuckers.”

Kyron wrote the song in Moriah Shock Incarceration Correctional Facility while serving seven months for criminal sale of a controlled substance. He spit the first verse for Heron over the phone and recorded the track following his release in January 1999. The song begins with a vocal sample of Esther Rolle’s “(If You See a Devil) Smash Him” and Kyron’s gripping opening words: “Aye yo, who shot Rudy in broad daylight for cash? / I woke up this morning and heard the news flash.” Kyron goes on to describe the murder scene, the suspects, and the fallout, all from his perch in Queensbridge: “I’m in my room smoking boom playing Nintendo, high off the indo.” It’s a well-written song.

The way “Who Shot Rudy?” spread was very 1999. A publicist from Tommy Boy gave an advance copy of Y2K: The Album to an editor from Ego Trip—best described as hip-hop’s version of Spy magazine—who then passed it along to a writer from the New York Daily News working on an article about anti-Giuliani lyrics in hip-hop. From there, the New York Post and local TV news latched onto the story, creating a short-lived tabloid frenzy.

Hip-hop media, for the most part, moved too slowly to cover the story in real time. Though online outlets like Hookt and Volume were gaining traction, hip-hop websites in ’99 were insignificant compared to their print counterparts. Monthly magazines like The Source, Vibe, and XXL, meanwhile, operated on three-month lead times, meaning that interviews happening in June wouldn’t appear in print until the September issue. A 550-word profile of Screwball in the September issue of The Source stated that the interview took place a week prior to the controversy.

By the time The Source article hit newsstands, the story had faded. Tommy Boy Records didn’t promote the record. Mike Heron says that the label stopped answering their phone calls. A video treatment featuring a Giuliani lookalike was rejected and the label pushed Y2K: The Album into fall. To this day, Poet maintains that Giuliani pressured Tommy Boy’s parent company, Time Warner, through intermediaries. “Time Warner,” he says, “pushed [the album] back because they got word from Giuliani’s people to slow that shit down.”

Throughout the storm, Screwball maintained that “Who Shot Rudy?” was not created for the sake of controversy, in contrast to 50 Cent’s “How to Rob.” In fact, Screwball were conflicted about the attention generated from the song. For one thing, the group didn’t want an album cut overshadowing Y2K: The Album. Members of the group also still had one foot in the street and were wary of additional scrutiny from the NYPD. Screwball had reason to worry.

“I got the call that they wanted to find out a little more about Screwball,” says Derrick Parker, a retired NYPD detective known as the Hip-Hop Cop who ran a special intelligence squad that concentrated on the rap community. He now runs a security consulting group. “I worked in the intelligence division, so I’m sure the mayor’s office called the chief of intelligence, who then called one of his subordinates, who then called my captain and said, ‘Handle this.’ That’s how it goes down the chain of command. That’s how it went down.”

Kyron had an open warrant for missing a court date, Parker says. “We went to his house to get him, picked him up, brought him into the office, and I interviewed him,” he remembers. “He wasn’t a bad guy. But he had an open warrant, so he went through the system and then he got out and that was the end of it.”

That was the end of Screwball’s momentum as well. Tommy Boy pushed Y2K: The Album back once again, eventually releasing the album on February 8, 2000. “By that point,” Heron says, “no one cared.” The group splintered following their 2001 follow-up Loyalty. In 2008, KL died from an asthma attack.

One aspect of Rich Nice’s duties at Columbia Records was to move fast and break things. Sony, like most major labels at the time, was somewhat of a bureaucratic goliath with even minor decisions deliberated in meeting after meeting among a rotating constellation of executives.

Take the Lord Tariq and Peter Gunz hit “Déjà Vu (Uptown Baby),” for example, which first appeared on college radio during the spring of 1997. Columbia didn’t shoot a video until fall. The song didn’t officially drop as a single until December. It wasn’t until June 1998, over a year since the record debuted, that the label released the Lord Tariq and Peter Gunz album Make It Reign. It sold poorly, peaking at no. 38 on the Billboard 200.

Rich Nice vowed not to wait for Columbia to get behind “How to Rob.” He decided to circumvent the label. “If I put it in the system, I would have to wait for approval. Weeks, maybe months would go by,” he says. “I did a white label outside the system.” A white label is a piece of vinyl sent to DJs with no label affiliation, no logo, and no press release, just the name of the song and artist written in marker on—you guessed it—a white label.

Here’s how it worked: Rich Nice took a mixed master of the song to an independent vinyl manufacturer in New Jersey where he ordered a set amount of copies of “How to Rob.” He paid the invoice. Within a week he received a box of 12-inch records. Then the street team got to work making sure the vinyl reached the right hands: the hottest DJs in clubs and on mixtapes and mixshows. Since it was 1999, Funkmaster Flex helped break the record, spinning it nightly on Hot 97.

As D-Dot had predicted back at the Hit Factory, “How to Rob” created a commotion in the industry. Jay-Z rebutted 50 at Hot 97’s annual Summer Jam concert (“I’m about the dollar, what the fuck is 50 cents?” he rapped, moments after the two met backstage), and Ghostface Killah confronted 50 in the Sony building (“Is that the kid 50 Cent?” Ghost shouted as they crossed paths near the elevators. “We got to holler.”) Ghost, Big Pun, Kurupt, Sticky Fingaz, and Wyclef also addressed it on their own songs.

“How to Rob” was engineered to thrive in the moment: an era of hip-hop where the short-lived post–Biggie and Tupac truce had evaporated and rappers were once again talking shit about each other. Subliminal disses were the weapon of choice at the time, making 50’s approach that much more explosive. “Viral wasn’t a word then,” Cory Rooney says, “but that’s what 50 was trying to achieve.”

The “How to Rob” stealth path from white label to radio hit went as such: Flex bumped the record. The morning show gossiped about it. He said what about who? Then it seeped into regular rotation. Poke says that within six days “How to Rob” was getting 40 spins a week at Hot 97. Mixshow DJs in Atlanta and Los Angeles soon started playing the record.

Standard record-label practice at the time was to go for radio adds—a bump to service the song into daytime rotation and then, hopefully, cross over to pop radio—once a song topped 350 to 500 spins a week. Poke says “How to Rob” peaked at 650 spins. And yet Columbia never pushed it at radio.

“It was primed for mainstream radio. All we had to do was go for adds. [Columbia] was like, ‘No video. No adds. Fuck out of here.’ Otherwise, the record would have done what [50 Cent’s 2002 hit] ‘Wanksta’ did,” Poke says. “Mind you, if we were at Interscope, Jimmy Iovine would have told the world to kiss his ass. He knows how to do that stuff. He didn’t care. Our complaints to Columbia at the time was ‘Yo, look, controversy wins. We need this and it’s working.’ They were like, ‘No, we got to tone this down.’” There are conflicting accounts as to why that happened.

Poke believes that Columbia backed down due to legal threats from artists named on the record. “We got legal letters from every record company,” he says. “We were getting so many legal affairs letters sent to us it was insane.” Columbia was also worried, he says, about the potential for violence.

Rich Nice, meanwhile, says Columbia initially distanced itself from the record—“Donnie Ienner called me and said, ‘This is bullshit. You can’t do that’”—but came around once it sniffed a hit. The problem was that they viewed “How to Rob” as a novelty song, and their short-term strategy was to promote 50 Cent as a novelty artist in the “Weird” Al Yankovic vein. “Columbia wanted to make it something distasteful and discrediting to the artist,” Rich Nice says, citing a scrapped video treatment that he found offensive. “They wanted to promote the song as comical as possible with a cartoon vibe … We told them that there is no coming back from that.”

“How to Rob” petered out on radio during the summer and was buried on the In Too Deep soundtrack in August. 50 was disenfranchised. He had delivered a hit record and the label let him down. His debut album, Power of the Dollar, was no closer to dropping. He was back in development hell.

Columbia Records tried for a do-over in early 2000 and Power of the Dollar was given an August 1 release date. In the meantime though, 50 Cent’s feud with Ja Rule and Murder Inc. turned physical following a scuffle in Atlanta and an altercation at the Hit Factory in March 2000, which resulted in 50 Cent suffering a stab wound; Murder Inc. rapper Black Child later took credit for the stabbing. 50’s street feuds also escalated. On May 24, 2000, days before he was to film a video for “Thug Love”—a paint-by-numbers radio single featuring Destiny’s Child—50 was shot nine times in front of his grandmother’s home in Jamaica, Queens. Columbia Records soon dropped him.

Blaming the label is the ultimate clichéd rap sob story, but in the case of 50 Cent and Screwball, the suits’ fears were realized. “Who Shot Rudy?,” which had limited commercial appeal to begin with, attracted the attention of the NYPD. “How to Rob,” meanwhile, created a whirlwind of problems that were later compounded with 50 Cent’s release of the song “Ghetto Qu’ran (Forgive Me).” Whereas he was merely antagonizing rappers on “How to Rob,” 50 was now revealing hood secrets. According to an affidavit, federal investigators believed that the May 2000 shooting was revenge for “Ghetto Qu’ran.”

Here’s how “How to Rob” and “Who Shot Rudy?” would play out in 2019: The song is uploaded to SoundCloud. Buzz builds on social media. It trends on Twitter. Rap media—or what’s left of it—posts about it. A cheap video gets filmed on an iPhone and is uploaded to YouTube within 24 hours. Soon, word spreads to larger outlets. An essay about “Who Shot Rudy?” appears on The Atlantic. Maybe, if the story has legs, MSNBC’s Chris Hayes interviews Screwball. As for “How to Rob,” one can only imagine the Bossip headlines.

“How to Rob” would also trigger a robust answer from the hip-hop community similar to UTFO’s “Roxanne, Roxanne”—or, if you are under the age of 45, Kendrick Lamar’s verse on “Control.” For at least two weeks, the dawning of each day would arrive with a new “How to Rob” response—and that’s not counting the keyboard gangsters on IG. And the artists themselves would keep the controversy alive every day with both 50 Cent and Screwball (especially 50) aggressively promoting and marketing the record on social media.

A major label likely wouldn’t be involved, but if it were, it would support the record. Record companies can’t stop an MP3. Once it’s out, it’s out. Plus, labels know that the old formula no longer works: No super producer, guest artist, or pricey sample guarantees a smash. Hit records are much more random in 2019.

“Now, labels welcome anything that has the potential to become viral. Anything. No matter what,” Rooney says. “The Catch Me Outside Girl went viral. She got signed. She now has a career. … She’s made over a million dollars just because she talked shit on the internet. Imagine now a guy who is so beyond that, so talented, so smart, someone who has so many more records to come out with. That would have been the beginning of a huge new platform.”

50, of course, built a huge platform following his epic mixtape run in 2002 that resulted in him signing with Shady/Aftermath. His proper debut album, Get Rich or Die Tryin’, was certified six-times platinum and he was arguably, the top rapper in the industry from 2003 through 2005. 50 remains connected to his own history. He perfected the gimmick of “beef marketing,” lining up feuds with Ja Rule, The Game, Fat Joe, Jadakiss, Nas, and others to promote his latest projects. Now, aside from his executive producer and costarring role on the Starz drama Power, 50 largely remains relevant as an online troll. He hasn’t had a hit record in nearly a decade.

Kyron Jones, who started writing “Who Shot Rudy?” while in boot camp, is also linked to his past. When I asked Mike Heron whether he had a contact for Kyron, he said, “Kyron is locked up.” A quick search reveals that is not entirely accurate. Kyron Jones was paroled in May 2019 from Lakeview SICF after nearly six years of incarceration. Poet believes we haven’t heard the last from Kyron. “He’s ready to get back on his feet and get back in the studio,” he says. “I know he’s got a lot of shit on his mind.”

Thomas Golianopoulos is a writer living in New York City. He has contributed to The New York Times, BuzzFeed, Grantland, and Complex.

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