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Rappin' *ss Singa

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Once a person becomes successful, it's hard to tell them anything. Basketball players win a ring and decide it's time to drop an album. Rappers get bored and decide they want to become soul singers. But, what happens when those who have carved out their niches as sensitive thugs or pretty boys attempt to put some bass in their voice and spit a mean 16? Recently, Pop's bad boy Chris Breezy revealed his penchant for rhyming. His hit "Look at Me Now" and the recently released "Real Hip-Hop Sh*t" will both surely encourage more singers to get their MC on. We hope that our look back at examples of R&B singers-turned-rappers makes them take a moment to consider (or, reconsider) the career change.

Tyrese

Tyrese

Rapping under the name Black Ty on his Alter Ego double disc, the Baby Boy star's brief foray into rap was a comedic godsend for the whole hip-hop community.
Rating: M

Akon

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Kon has too many hip-hop sensibilities not to indulge on the mic. He's rhymed on Kardinal Offishal's "Graveyard Shift," among other tracks.
Rating: M

Trey Songz

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We were skeptical when Trigga first started rhyming on songs like "Wonder Woman," but as time's gone on we've come to appreciate his cleverly raunchy punchlines.
Rating: XL

Justin Bieber

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He’s no R&B singer, but even the Biebz has tried his hands at rapping. He’s released a freestyle over Vado’s “Speaking in Tongues” and another offering on Tim Westwood's radio show.
Rating: M

Sean Garrett

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The singer/producer and jack-of-all trades didn't surprise anyone when he picked up the mic and tried to rhyme. See "In Da Box" featuring Rick Ross.
Rating: L

Angie Stone

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Year before becoming known as a soulful singer, Angie Stone was signed to Sugar Hill Records as part of The Sequence.
Rating: L

Ryan Leslie

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His voice and delivery still seem a bit forced when he rhymes, but R Les's witty bars were hard to ignore on Kanye's "Christian Dior Denim Flow."
Rating: L

R. Kelly

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From the beginning, Robert never confined himself to just singing. See: Big Tymer's "Gangsta Girl"
Rating: L

Ne-Yo -

Ne-Yo

Though we prefer the “gentleman” as a singer, it's hard for us to hate on his 2008 freestyle over "A Milli."
Rating: L

Mary J. Blige

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The Queen of Hip-Hop/R&B's vocals have graced the choruses of many a classic hip-hop track, but don't forget that Ms. "No More Drama" can also also flow.
See "Enough Cryin'" where she spits under the moniker Brook Lynn. Rating: XL

Erykah Badu

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MC 's are not only Ms. Badu's romantic preference, but also her role models. She proved on "Love of My Life Worldwide" that she could go off the top with certified femcees like Queen Latifah and Jay Electronica.
Rating: L

Madonna

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Even Madge felt it necessary to spit a few bars on the title track to her 2003 LP, American Life. She even uses a little Auto-Tune pre-T-Pain on the track. Words like yoga and pilates probably never would have made it onto a rap song if not for the material girl.
Rating: M

Ciara

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It's no surprise that the songstresses aggressive singing style translates well when she rhymes. See: Missy Elliot's "Lose Control"
Rating: L

Brandy

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Under the name Bran' Nu, Brandy began rapping with the help of super-producer Timbaland in late 2009. Few remember... for a reason. See: "Meet in the Middle"
Rating: M

Beyonce

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Beyonce's rapid-paced flow in her early singing days as a member of Destiny's Child foreshadowed her experimentation as an MC. See: "Diva."
Rating: L

Chris Brown

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Now known more for blonde hair and violent outbursts than his dance moves, it only makes sense Breezy evolve his bad boy image by stepping to the mic. "Real Hip-hop Shit" will not be the last time we hear him MCing.
Rating: L