Hip-Hop Valentines: The 14 most romantic rap songs

Categories: Lists, Rap/Hip Hop
Valentines Day is here and you need some help to win over the heart of that sexy B-girl or B-boy?

We know hip-hop doesn't have the best history romancing the opposite sex, "bitches better having my money" and "skeeting on walls" doesn't really set the mood. But a bunch of the fellas in the booth had a more thoughtful outlook on their female counterparts. Among them are LL Cool J, Andre 3000, and even Slick Rick.

So don't worry, we have you covered. So grab your girl's or guy's hand, hit the park bench with the boom box, and let's discover some good ol' boom bap romance.

14. "Hey Lover" - LL Cool J

This is what happens when you mix LL Cool J with the romantic styling of Boyz II Men, you get this gem. Just like his first ode to females "I Need Love" that started the love movement in Hip-Hop, this song made the trendy rapper and R&B collaboration a sure thing for years to come.

Lines like "...besides he drinks too much and smokes too many blunts/ and I'll be working out everyday thinking about you" calls to the common problem of the beautiful woman dating the drunk douche bag. While LL lifts weights, licks his lips, and fantasizes about tropical vacations the douche bag wins in the end as James Todd Smith drives off alone with his multi-million dollar FUBU endorsement.

13. "What's on Your Mind?" - Eric B & Rakim

A common problem with women traveling mass transit is that they always got to encounter the guy trying to holler. It's no different in New York City; this tale is about Rakim trying to pick up a girl on the subway.

First she plays him off with the cold shoulder, but a few stops later she warms up. Before long, the romantic warrior in Rakim wins her over with a long courtship but after watching Bill Cosby at the Apollo they finally knock boot.

Who knew Pudding Pops were the key (taking notes). It also helps that the slick sample of "Curious" by Midnight Star was in the background massaging the mind.

12. "You Got Me" feat Jill Scott and Eve - The Roots

First off, Jill Scott sang on the original but got dumped for the better-looking Erykah Badu for the video remix. That alone dropped this down the list. Love knows all shapes and sizes, plus how you going to do Jill like that?

Black Thought spits away about his love for his woman and his love for the road, a then unknown Eve spits the woman's side of the story in a gone 'til November type tale. To every hip-hop indie hipster this is pretty much the nail in the coffin for that neo soul girl you just met at the coffee shop; just don't bore her with your own poetry.

11. "21 Questions" feat Nate Dogg - 50 Cent

Who can blame Curtis? When you have as much money as he does, you have to ask a lot of questions. How about 21 of them? I love this song as much as a fat kid loves cake.

So you got to annoy her with questions about being poor, driving crappy cars and working at Burger King. Then again, if she looked like Megan Good, I might just give her a pass. But funny thing, the next single was about how Curtis improved his financial gain and profits by employing women to service other men. Were these 21 questions just an interview for a job? How romantic.

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