David Berkowitz, the "Son of Sam" serial killer who was arrested in 1977 after a year-long killing spree in New York City, is among the most notorious criminals to have served time in prison on Rikers Island. From July 1976 until he was arrested in August 1977, Berkowitz killed six women and injured several more, leaving cryptic letters at his crime scenes signed by "the Son of Sam." The 24-year-old postal worker from Yonkers pleaded guilty in 1978, saying his neighbor's demonic dog had told him to commit the crimes. Berkowitz enlisted in the army in 1971 and became known as an excellent marksman. After he was arrested, Berkowitz ironically confessed he believed he was a soldier in Satan's army, instructed to target dark-haired women and terrorize the city of New York. He was denied parole in 2002 and remains incarcerated at the Sullivan Correctional Facility in upstate New York.
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Robert "Joe" Halderman, the former CBS 48 Hours producer spent four months behind bars at Rikers in 2010 for attempting to blackmail David Letterman. Halderman threatened to reveal that David Letterman had slept with female staff members if the Late Show host did not give him $2 million. Letterman chose to come clean himself rather than giving Halderman the hush money. Halderman's lawyer said jealousy and financial issues drove him to come up with the extortion plot. His girlfriend worked on Letterman's Late Show and allegedly detailed her sexcapades and relationship with the host in her diary, which Halderman discovered before subsequently plotting his revenge.
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Originally from the Bronx, Guy Velella served as Republican state senator for 28 years and was particularly popular amongst Democrats and Republicans alike in New York City. But the senator was forced to resign in 2004 after being charged with conspiracy and accepting $137,000 in bribes to help people win state public works contracts. He was sentenced to a year in prison and ultimately spent 182 days on Rikers Island before he was released on bail.
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Sonny Rollins was born in 1930—a decade after the Jazz Age first hit New York City—and became a renowned improv master and soulful saxophonist in the '40s and '50s, recording alongside jazz luminaries like Miles Davis and Bud Powell. But like many be-bop artists of the time, Rollins was into the drug scene and went through a rough patch. In 1950, he was arrested for armed robbery and given a three-year jail sentence on Rikers Island. The saxophonist ended up spending 10 months in the clink before being released on parole.
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Radio stations played rapper DMX's hit single "Party Up (Up in Here)" on repeat when it came out in 1999. But the hip-hop artist from Yonkers definitely had some inner demons (his first album was titled It's Dark and Hell Is Hot & Flesh of My Flesh, Blood of My Blood). He ended up having several run-ins with the law, including attempted vehicle theft, driving without a license, and using cocaine. He was arrested in 2005 after he failed to submit to a drug test and refused to undergo treatment. He spent 40 days behind bars at Rikers.
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On March 8, 2010, Lil Wayne was sentenced to a year in prison at Rikers after pleading guilty to weapons charges. The tough rapper initially took the sentence in stride and claimed he wasn't worried about the harsh conditions at Rikers: "This is Lil Wayne going to jail. Nobody I can talk to can tell me what that's like. I just say I'm looking forward to it." But he ended up violating prison rules in order to make it through his yearlong sentence. An iPod charger and headphones (both prohibited at Rikers) were found hidden in his cell. In a prison call he told DJ Scooby Doo, "I can't live without my music. You know how it is, man… I had to take my little slip up."
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Sex Pistols member Sid Vicious spent seven weeks at Rikers, starting toward the end of 1978. In October 1978, police found his girlfriend dead from a stab wound in the Chelsea Hotel in New York; Vicious became the prime suspect. While in a holding cell, he confessed, "I did it because I'm a dirty dog." His story kept changing throughout his questioning. Vicious was charged with second-degree murder and released on bail. In December of that year, he was sent to prison on Rikers Island following a fight at a New York City nightclub. He spent seven weeks there and was released on February 1, 1979. Vicious went to a party that night to celebrate his freedom, and was found dead of a drug overdose the next morning.
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In addition to a successful career in entertainment, rapper Tupac Shakur had some serious legal problems. He was arrested in 1992, after a 6-year-old boy was killed by a stray bullet during an altercation between Shakur and two others. In 1993, he was charged with shooting two off-duty police officers in Atlanta, though both cases were later dismissed. Shakur was charged with sexual assault in 1994, and he received a sentence of one and a half years to four and a half years in prison; he only served eight months. He spent a portion of his sentence at Rikers. While he was in prison, his album Me Against the World went to the top of the Billboard chart, making him the first artist to have a No. 1 on the chart while in prison.
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Type O Negative frontman Peter Steele did a stint at Rikers in 2005, for drug possession and assault. As he described it, he was arrested for "accidentally punching someone in the face 50 times." His period of incarceration led to a rumor that he had died in 2005, complete with a photo of his gravestone on the band's website, but he would not really die until 2010. Of his time in prison, he said, "To be white in jail and to have long black hair and fangs is not an advantage. I was in maximum security, and there were some pretty scary people in there who are never gonna get out, so they had nothing to lose by messing with me. Fortunately, I'm six-foot eight, so I'm not exactly a target."
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Former New York Giants player Plaxico Burress began serving a sentence at Rikers in September 2009. His crime was accidentally shooting himself in the thigh with his own Glock, while drinking in a crowded nightclub. With good behavior, he will be eligible for release in June 2011.
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Rapper Foxy Brown was sent to Rikers after a series of probation violations. In 2004, she received three years of probation for assaulting two manicurists. In 2007, she got kicked out of an anger management class—for anger issues—and then went to Florida, both of which were violations. Then she was finally sent to Rikers Island in 2007 for allegedly hitting a neighbor in the face with her BlackBerry. She was released in April 2008, after serving eight months in prison, including 40 days in solitary confinement.
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Mark David Chapman was sent to Rikers soon after killing John Lennon. The former maintenance man from Hawaii was housed there and underwent psychiatric evaluations. Since his sentencing, he has served his time at Attica in upstate New York, and has been denied parole six times. Of the killing he said, "I just saw his face and it seemed like it all came together, the solution to my problem of being confused and seeming like a nobody. And I said, 'Wouldn't it be something if I killed this individual? I would become famous, I would be something other than a nobody.' And that was my reasoning at the time." He now says, though, that he is " ashamed" of the crime.
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