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Rap Songs About Women: 25 Classics for Valentine's Day

Posted Feb 13th 2013 2:00PM by Theo Bark
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Hip-hop and Valentine's Day go together like the cast members of Love & Hip-Hop. Which is to say, well, not that swimmingly. But whatever. Some of the genre's most enduring contributions, in any era, have been songs about the ladies. From A Tribe Called Quest and the Pharcyde's attempts at courtship to Slick Rick and Too $hort's 'Freaky Tales,' we've collected 25 of rap's most memorable songs about women, limiting each artist to one classic contribution.

'Bonita Applebum'

A Tribe Called Quest

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A Tribe Called Quest's ode to a high school crush with the proper measurements -- 38-22-27 -- this sitar-powered, RAMP-sampled Q-Tip solo takes us back to the silk shirt era of East Coast rap, when having "crazy prophylactics" was a reason to brag. While their contemporaries were telling lurid sex stories and entering into the early stages of gangsta rap, Tribe was just trying to get put on.

'Bitties in the BK Lounge'

De La Soul

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De La Soul's Pos and Trugoy play both sides of the counter on this 1991 tale about the sharp-tongued ladies of the Burger King lounge, who "kiss and scrounge" for Trugoy's autograph, as he attempts to place an order. On the flip side, they diss his partner Pos for working in fast food. 'Bitties' exemplified the Long Island group's everyman approach, whether being recognized as "that guy" while trying to buy a burger, or getting called out for being a lowly burger flipper by a saucy bitty in the lounge.

'Around the Way Girl'

LL Cool J

David Becker, WireImage

Utilizing one of rap's earliest pitched-up vocal samples, LL Cool J's tribute to the independent neighborhood chick with the bamboo earrings more than made up for his saccharine single 'I Need Love.' Still one of the most notable songs of its era, while others glamorize gangsta love, 'Around the Way Girl' describes the ideal hip-hop chick.

'Put it in Ya Mouth'

Akinyele

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Though Queens rapper Akinyele's debut album, 'Vagina Diner,' had a lewd title, production by Large Professor and cuts by X-Ecutioner Rob Swift, the masses will always remember him for is his 1996 ode to oral sex -- a soundtrack staple at every frat party ever. The track was full of lewd sound effects and even lewder lines like "Put your lips here/ And catch these damn facial hairs in your mouth."

'Ms. Jackson'

OutKast

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Although OutKast have released several songs that could make this list, from their dance floor ode to civil rights leader Rosa Parks, to their stirring tribute to fictional hood rat Sasha Thumper, 'Ms. Jackson,' a dedication to Erykah Badu's mother, with its sneaky nod to Wagner's 'Bridal Chorus' -- the 'Wedding March' -- got us all hearing wedding bells.

'Jailbait '

Busy Bee

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Probably the least-known inclusion on this list, Busy Bee's 1992 song about "messing with a girl who was only 12 ... who looked as fine as I felt" is completely perplexing. While several old schoolers rapped about a similar topic, including Grandmaster Flash and Boogie Down Productions, Busy Bee's is by far the most bizarre.

'Girls'

Beastie Boys

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Adrock's two-minute catchy-obnoxious solo tells the story of a girl around the way who, "liked my homepiece MCA/ But he who would not give her play," although her pants were tight. After she rebuffs the narrator's advances, Adrock reveals that he's only feeling girls with new wave hairdos "to do the dishes/ To clean up my room/ To do the laundry/ And in the bathroom." Hard to believe the Beastie Boys went on to become a bunch of green-conscious Buddhists-political activists.

'All That I Got Is You'

Ghostface Killah

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Over a string sample from the Jackson 5's 'Maybe Tomorrow,' Ghostface Killah's Mary J. Blige-accompanied tribute to his struggling mother still gives chills. Arguably the Wu-Tang rapper's most vivid lyrical offering, the 1995 single featured lines like, "Four in the bed, two at the foot, two at the head/ I didn't like to sleep with Jon-Jon, he peed the bed/ Seven o'clock, pluckin' roaches out the cereal box." Unforgettable.

'Sally Got a One Track Mind'

Diamond D

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Over a loop from Jack Bruce's oft-sampled 'Born to Be Blue,' Diamond D waxes lyrical on the subject of Sally, whose wealthy upbringing caused her to turn into a "neighborhood hoe." Though Diamond warns that she needs to "wake up and smell the blunt," unfortunately Sally ends up a "slave to material things/ And now ya snack on four chicken wings," which is apparently not a good look.

'Sometimes I Rhyme Slow'

Nice & Smooth

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Greg Nice uses his verse on the Tracy Chapman-sampled classic to discuss a variety of subjects, including unpopular candy Chico Stix, Timbs, driving a red Sterling and going to Tavern on the Green for a glass of wine. Smooth B then comes through with a heart-wrenching tale of cocaine-addicted Jane Doe, who takes advantage of his love and crashes his whip. Though he considers shooting her with his 9mm, he instead decides to let her back in "and now she's sniffing again." Life's real.

'Ms. Fat Booty'

Mos Def

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Over Ayatollah's Aretha Franklin flip, Mos Def recalls Ms. Fat Booty, graced with an "ass so fat that you could see it from the front." She plays him at their first meeting, but when he's later introduced by his rap name, she comes around and apologizes. Weeks of late night talks lead to a night of Gregory Isaacs and Sade, after which Mos smashes her "like an Idaho potato." Yet she's commitment-phobic, and ends up with a bangin' ass lesbian. Mos Def at his prime, over one of the Rawkus era's best beats.

'Looking at the Front Door'

Main Source

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Arguably hip-hop's greatest breakup song, Large Professor opens with the clunker "We fight every night, now that's not kosher," and also tries to "Front like everything's hunky dory," yet somehow Main Source makes it sound ill. You'd be hard-pressed to find a better go-to when you break up with your miss.

'Freaky Tales'

Too $hort

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Too $hort name-checks a relentless stream of flammy fiends, lizards and skeezers on this lurid epic, which clocks in at over 10 minutes. He pontificates on the subject of Michelle, whose "booty was bigger than a tale on a whale," Janet, whose "ass was bigger than the whole damn planet," Belinda the Blender who "gave head like she made it up" and 35 other women of ill repute.

'Hey Ma'

Cam'ron featuring Juelz Santana

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The most recent song on this list is also our go-to karaoke jam, an undeniable tour-de-force of one-liners from Cam and his young protégé Juelz, who steals the show, dropping crazy knowledge on the ladies. While downtown clubbin' -- at a ladies night -- and living "the crazy life," Juelz graciously offers to "tell 'em what the '80s like," but admonishes shorty not to "touch nothin'" in his car, followed by the classic exchange, where Cam calls up, big brother style, to find out if he hit -- he did, and then some.

'Passin' Me By'

The Pharcyde

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While 'Otha Fish,' or 'She Said' could have also made this list, 'Passin' Me By' is the Pharcyde's 'T.R.O.Y.,' a song committed to memory by millions, pairing the Quincy Jones and Jimi Hendrix samples perfectly with the group's melodic verses about unrequited nerd love, back when hip-hop was a little more relatable to its fans.

'Cave Bitch'

Ice Cube

David Wolff - Patrick, WireImage

A dedication to the white women of the world, with a special introduction by the outspoken Dr. Khalid Muhammad, this violent condemnation angered many, entertained more, introduced the word "caucazoid," managed to slip in a Charles Barkley diss and also contained Ice Cube's assertion that "You can't get mine, hoe/ I'd rather f--- an albino." At least we knew where Cube was coming from.

'Jane'

EPMD

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The epic saga of EPMD and Jane began in 1988 with EPMD's debut 'Strictly Business,' and continues with each album, telling the convoluted tale of gangsta Jane, who may or may not be dead, may or may not be setting the duo up and ultimately turned out to be a transvestite, maybe. "Who killed Jane/ Not the squad kid, I think we been framed." It's a rap odyssey.

'Renee'

Lost Boyz

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A song about a honey named Renee whom Mr. Cheeks -- pause -- met one day, on his way back from John Jay Criminal College. She told him "she wants to be a lawyer, in other words shorty studies law," -- best line ever -- and they end up at her apartment, where he concludes from her collection of "crazy CDs" that she "got cheese." A couple weeks later she gets shot.

'Gangsta Bitch'

Apache

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Produced by A Tribe Called Quest, Apache's sole hit was a tribute to the Bonnie and Clyde lifestyle, playfighting with machetes, "Goin' to the movies, packin' his and her nines/ Wearin' Carhart and leather, motherf--- the weather/ On Valentine's Day, doin' stick ups together." Though Apache passed away in 2010, his dream lives on.

'Teenage Love'

Slick Rick

Raymond Boyd, Michael Ochs Archives

'Treat Her Like a Prostitute' and 'Mona Lisa' introduced Slick Rick's profane, cocksure storytelling, yet 'Teenage Love' revealed the Bronx rapper's sensitive side, discussing the trials of young love over the Bomb Squad's lush live instrumentation. Before the film 'Blue Valentine,' there was Rick's 1988 debut single, bumming out about young lovers and reminding them of the inevitability of a relationship's ultimate demise. Instant nostalgia.

'Dear Mama'

Tupac

Al Pereira, Michael Ochs Archives

Though Tupac debuted with his conscious hip-hop single 'Brenda's Got a Baby,' when he released his 1995 single 'Dear Mama,' it still came as a surprise that the hardcore gangsta rapper would release such a heartfelt song. The dedication to his "crackfiend" mother Afeni Shakur earned inclusion into the Library of Congress' National Recording Registry, and a place in the hearts of millions, including Eminem, who once stated that it was his favorite song.

'Girls, Girls, Girls'

Jay-Z

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In this gentleman's version of 'Freaky Tales,' Jay-Z muses about his various girls around the globe, including an Indian -- red dot or feather? -- a "chick from Peru that sniff Peru," a Chinese bootlegger and an African Eddie Murphy fan, but the project chick is ultimately his heart. The hook gives a strong nod to the old school, interpolating Crash Crew's 'High Power Rap,' and Biz Markie, Slick Rick and Q-Tip's voices can all be heard on the chorus.

'Just a Friend'

Biz Markie

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Biz Markie's whimsical tale about friend-zone exile borrowed liberally from Freddie Scott's '(You) Got What I Need,' which was all good at the time. Two years later, Biz would lose the first major hip-hop copyright infringement case, forever changing the game. His maniacal Mozart-at-the-piano impression in the music video flipped our wigs.

'Mahogany'

Rakim

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Rakim's approach to a song about a woman was typically metaphorical, drawn out and intricate, and of course, included rocking a crowd. Over a classic Al Green loop, Ra's courtship was mature and reserved, making similar attempts seem simplistic in comparison.

'I Used to Love H.E.R. '

Common

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Common's 1994 single was an extended metaphor, addressing hip-hop as the object of the young Chicago MC's affections and criticism. Bemoaning hip-hop's descent into the mainstream, and divergence into gangsta rap, from its conscious, Afrocentric roots, the song sparked a legendary battle with Ice Cube, and inspired a relentless stream of vastly inferior copycats. "She was really the realest before she got into show biz," right Com?