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Some of us were shocked to hear that Lauryn Hill went to jail for tax evasion, but Lauryn’s stint in jail was just part of a bumpy ride to the bottom of the charts. From her Fugees days to her bizarre new single, here are 15 things we bet you didn’t know about Ms. Hill.

Wyclef Jean

Wyclef and Lauryn had a long, dramatic affair — while Wyclef was married to his wife Claudinette. According to Wyclef, the relationship and The Fugees broke up when Lauryn pretended to be pregnant with his baby to break up his marriage. When Wyclef found out the truth, he was done with Lauryn romantically and professionally.

Legal Trouble

The success of “The Miseducation of Lauryn Hill” may have been the beginning of Lauryn’s troubles. Soon after the album dropped, production company New-Ark sued Lauryn for $5 million for uncredited production and songwriting contributions. Lauryn paid up, but a friend called the incident “The beginning of a chain effect that would turn everything a little crazy.”

Love Trouble

While Lauryn was with Wyclef, she met Rohan Marley and had his baby. It was the start of a 15 year-long affair (they never married because Rohan never divorced his first wife). The affair ended in 2011 when Lauryn repeated history and got pregnant with another man’s baby

The Pressure

After “The Miseducation of Lauryn Hill” blew up, the whole world knew Lauryn’s name. In 2000, Lauryn wanted privacy so bad that she stopped going out, fired her manager and went to Bible study five days a week.

“Brother Anthony”

In 2002, Lauryn went on MTV and made everyone uncomfortable when she started talking about her “spiritual advisor” Brother Anthony who had “an understanding of the Bible like no one else I ever met in my life.”

But Brother Anthony is known in a lot of circles as a cult leader. Hill’s family says he has a hold on her life and is responsible for a lot of her strange behavior.

All Those Kids

Lauryn has six kids. She had five of them between 1997 and 2002. Because she spent most of that time knocked up, she had to drop out of “Beloved” (she was replaced by Thandie Newton), “Charlie’s Angels” (she was replaced by Lucy Liu), “The Bourne Identity” and the “Matrix” trilogies.

Going Unplugged

In 2001, when Lauryn performed “MTV Unplugged No. 2.0,” fans didn’t know whether to laugh or cry. That album was the craziest thing people had heard in a long time.

Rolling Stone called it “a public breakdown” and the Los Angeles Times said Lauryn should get ready for jokes about her being “unhinged.” But there was nothing funny about the album’s sales. They totaled a little less than 500,000 copies worldwide.

Abandoning the Kids

The conscious songstress started The Refugee Camp Youth Project soon after her solo album made it big, but in 2002, Lauryn suddenly shut it down because she was bored and now devoting time to the kids felt like “slavery”. So she pulled the funding and let the kids fend for themselves.

Highway Robbery

In 2004, Lauryn released the song “Social Drugs” and charged visitors of her website $15 to view the video three times before their viewing privileges expired. She also sold autographed posters and Polaroids on her site for around $500+ a pop.

Failed Reunion

In 2005, The Fugees tried to reunite for a European tour, but Pras and Wyclef said they just couldn’t do it. They say Lauryn made them call her “Ms. Hill” and showed up late to every practice. The reunion fell apart before they could record an album.

Her Tour

Lauryn’s solo touring didn’t do much better. She had a habit of showing up 2+ hours late and fans didn’t appreciate it when she played the remixes instead of the classics. A few of her concerts ended early when fans booed Lauryn and walked out.

A Private Meltdown

In 2008, Lauryn Hill moved back with her mother in South Orange, New Jersey. She was still writing music but in a way that made Rohan Marley nervous: “She writes music in the bathroom, on toilet paper, on the wall. She writes it in the mirror if the mirror smokes up. She writes constantly. This woman does not sleep,” he said.

Falling Out and Ripping Off

In 2009, Lauryn Hill passed out on stage during the second performance of her tour. After that, she cancelled the rest of the tour — and refused to give fans their money back.

Trouble with Uncle Sam

Lauryn’s May 2013 sentencing wasn’t even the craziest part of the trial. Lauryn told the judge that she didn’t pay taxes on $2 million in earnings because “pop culture’s climate of hostility, false entitlement, manipulation, racial prejudice, sexism and ageism” kept her from working. And furthermore, as a child of former slaves, she couldn’t function in the economic system imposed on her people in America.

“Neurotic Society”

Lauryn Hill is back in the studio thanks to a court order. But we don’t know if Lauryn’s new music has what it takes to pay the bills. Her recent single “Neurotic Society” didn’t make headlines because it was jamming but because in the lyrics, Lauryn blamed the world’s social problems on gay rights.

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