Lauryn Hill's Top Ten Greatest Hits

First Female Artist To Win Five Grammy Awards in One Night

Born May 26, 1975 in East Orange, New Jersey, Lauryn Hill made history at the 41st annual Grammy Awards on February 24, 1999 in Los Angeles, California when she became the first female artist to win five Grammys in one night. She was honored for Album of the Year and Best R&B Album, (The Miseducation of Lauryn Hill), Best New Artist, and two awards for "Doo Wop (That Thing)"-- Best R&B Song and Best Female R&B Vocal Performance. Her debut solo album, The Miseducation of Lauryn Hill, has sold over 19 million copies worldwide.

Since that release, Hill began a self-imposed exile and has worked sporadically. Her only other solo release was her live CD, MTV Unplugged No. 2.0, in 2002. Hill has six children, five of whom are with Rohan Marley, the son of Bob Marley. In 2012, she pleaded guilty to tax evasion for failure to pay federal income taxes, and in 2013, served a three-month prison sentence. Two years later, she was featured along with Usher, Mary J. Blige, and Common on the soundtrack of the Nina Simone documentary, What Happened, Miss Simone? She sang six songs on the CD, Nina Revisited… A Tribute to Nina Simone

During her career, Hill has won eight Grammys, five MTV Video Music Awards, five Soul Train Music Awards, four NAACP Image Awards, three American Music Awards, three World Music Awards, and two Billboard Music Awards.,

Hill began her entertainment career as a teenage actress, appearing in a recurring role on the television soap opera, As the World Turns. She was also featured in the film Sister Act 2: Back in the Habit which starred Whoopi Goldberg. She met Pras Michel in high school and formed a group called Tyme. Michel's cousin, Wyclef Jean, joined them and they changed their name to The Fugees. The trio released two albums, and their second CD, The Score in 1996, hit number one on the Billboard 200. It sold over six million copies in the United States, and earned Grammy Awards for Best Rap Album, and Best R&B Performance by a Duo or Group with Vocals for "Killing Mme Softly." Following the success of The Score, each member launched their solo careers. The Fugees reunited briefly in 2005 for a European concert tour.

During her career, Hill has also collaborated with numerous stars including Aretha Franklin, Carlos Santana, Bob Marley, Ronald IsleyJohn Legend, D'Angelo, Nas, and Method Man.

Here are "Lauryn Hill's Top Ten Greatest Hits."

01
of 10

1998 - "Doo Wop (That Thing)"

Lauryn Hill. SGranitz/WireImage

From the 1998 The Miseducation of Lauryn Hill CD, "Doo Wop (That Thing)" won Grammy Awards for Best R&B Song and Best Female R&B Vocal Performance. It was Hill's second debut solo single, and it was the tenth song in history to debut at number one on the Billboard Hot 100.

02
of 10

1996 - "Killing Me Softly" with The Fugees

The Fugees. Jeff Kravitz/FilmMagic

The Fugees' hip-hop cover version of the Roberta Flack classic "Killing Me Softly" from the 1996 The Score album reached number one on the Billboard R&B chart, and number two on the Hot 100. It won a Grammy Award for Best R&B Performance by a Duo or Group with Vocals.

03
of 10

1997 - "The Sweetest Thing" featuring The Refugee Camp All-Stars

Lauryn Hill. Frank Micelotta/ImageDirect

Lauryn Hill recorded "The Sweetest Thing" with the Refugee Camp All-Stars (consisting of Pras from The Fugees and John Forte) for the the 1997 Love Jones soundtrack. It was her first release without The Fugees, and it reached number two on the Billboard R&B chart.

04
of 10

1998 - "Nothing Even Matters" featuring D'Angelo

Madonna, Lauryn Hill & Paul McCartney. KMazur/WireImage

D'Angelo is featured on "Nothing Even Matters" from The Miseducation of Lauryn Hill. It was nominated for a Grammy Award for Best R&B Performance by a Duo or Group with Vocals.

05
of 10

1999 - "Turn Your Lights Down Low"

Launryn Hill and Carlos Santana. Ron Wolfson/Hulton Archive

Lauryn Hill covered the Bob Marley and The Wailers song "Turn Your Lights Down Low" for the 1999 Chant Down Babylon album. The song was nominated for a Grammy Award for Best Pop Collaboration with Vocals.

06
of 10

1999 - "Ex-Factor"

Lauryn Hill. Steve Granitz/WireImage

"Ex-Factor" was the second single from The Miseducation of Lauryn Hill album and reached number seven on the Billboard R&B chart in 1999.

07
of 10

1998 - "Can't Take My Eyes Off You"

Lauryn Hill. Kevin Mazur/WireImage)

"Can't Take My Eyes Off You" from The Miseducation of Lauryn Hill was nominated for a Grammy Award for Best Female Pop Vocal Performance.

08
of 10

2005 - "So High" with John Legend

Lauryn Hill. Scott Gries/Getty Images

Lauryn Hill recorded "So High" with John Legend for his 2005 Get Lifted album and it was nominated for a Grammy Award for Best R&B Vocal Performance by a Duo or Group.

09
of 10

1998 - "Lost Ones"

Mary J. Bkige and Lauryn Hill. Kevin Mazur/WireImage

"Lost Ones" from The Miseducation of Lauryn Hill was nominated for a Grammy Award for Best Rap Solo Performance. The song exemplified Hill's unique versatility, as she was one of the few artists to receive nominations in the R&B and Rap categories for the same album,

10
of 10

2002 - "Mystery of Iniquity"

Lauryn Hill. David Corio/Michael Ochs Archives/Getty Images

From Lauryn Hills' 20002 MTV Unplugged No. 2.0 CD, "Mystery of Iniquity" was nominated for a Grammy Award for Best Rap Solo Performance.