Imaginary Players: The 20 Greatest Fictional Rap Characters Of All-Time

Mr. Wendal

First appearance: Arrested Development’s 3 Years, 5 Months & 2 Days in the Life Of… (1994)

You can learn a lot from a bum, fact not fiction.

Bonita Applebum

First apperance: A Tribe Called Quest’s People’s Instinctive Travels and the Paths of Rhythm (1990)

If love/lust is a drug, Bonita Applebum would be the dealer. Although she’s now a full-grown woman (possible MILF), she can still put a spell on you.

Michael Young History (My Cool Young History)

First Appearance: Lupe Fiasco’s Food & Liquor (2006)

A rap tale from the crypt if there ever was one, Lupe’s walking dead hero was the main inspiration for his incredible 2nd album.

Shameek from 212

First appearance: Wu-Tang Clan’s Enter the Wu-Tang (36 Chambers) (1993)

Shameek’s demise happened off-screen but he was immortalized in one of the most lively skits in Hip-Hop history.

Ms. Jackson

First appearance: Outkast’s Stankonia (2000)

Dedicated to all grandmothers who got caught in the crosshairs of baby-mama-daddy beef.

Jane

First appearance: EPMD’s Strictly Business (1988)

When Michael Jackson was shooting up clubs for Annie, he should have looked out for Jane too. She had a rough life, b.

The Little Ghetto Boy

First appearance: Dr. Dre’s The Chronic (1992)

There’s a little wild child in all of us and that’s really what the song represents.

Dr. Trevis

First apperance: Redman’s Whut? Thee Album (1992)

The good Funk Doctor is still doing his thing but for those missing his old sound, it was this type of wackiness that propelled the high level of lyricism.

Bl*wj*b Betty

First appearance: Too $hort’s Raw, Uncut & X-Rated (1986)

Um…does Ms. Betty really need some sort of explanation?

Aunt Dot

First appearance: Lil Kim’s The Notorious K.I.M. (2000)

It’s always convenient to have a clean-up (wo)man in your family.

Damien

First Appearance: DMX’s It’s Dark and Hell is Hot (1998)

Who knew the man downstairs was the Sincere to X’s Tommy? Explains all his struggle visits to the bing.

CB4

First appearance: CB4 (1993)

Chris Rock and the gang trolled Hollywood so hard that the soundtrack actually made the Billboard charts.

Roxanne

First appearance: UTFO’s self-titled album (1985)

Although Roxanne was a fake chick (figuratively and literally), it didn’t prevent her from receiving dozens of responses and spawning the career of some of the first female rappers. That’s power of the P at work.

Tariq

First appearance: Prince Paul’s A Prince Among Thieves (1999)

Rapper Breezly Brewin held down the Oscar-worthy performance for Prince Paul’s unforgettable concept album.

Sherane a.k.a Master Splinter’s daughter

First appearance: Kendrick Lamar’s good kid, m.A.A.d city (2012)

It’s not everyday that an encounter with a hoodrat can groom you into rap’s biggest attraction.

Mr. Ouija

First appearance: Bone Thug-N-Harmony’s Creepin’ on ah Come Up (1994)

It’s never been confirmed if the ouija ever talked back to the Bone Thugs boys but this was some excellent display of harmonizing.

Shorty Doo-Wop

First appearance: Nas’ Illmatic (1994)

Yo, we’re not saying this never really happened but…this never really happened.

Stan

First appearance: Eminem’s The Marshall Mathers LP (2000)

What started as a classic song transformed into classic slang used to describe the hardest of tipriders.

The Mad Rapper (Deric “D-Dot” Angelettie)

First appearance: The Notorious B.I.G.’s Life After Death (1997)

Who would have thought a little comedic relief would have spawned hashtag phrases and immediately thrust 50 Cent into a controversial career?

Brenda

First appearance: 2Pac’s 2Pacalypse Now (1991)

Twenty something odd years and Teen Mom is still on TV. Tupac did not die to become a DJ Khaled martyr for this foolishness.