As Valentine's Day quickly approaches, plenty of hip-hoppers are either planning that great romantic gesture for a special someone or reflecting on past loves and choosing the right playlist to fit the mood. That's why, this time of year, we're often reminded how many rap love songs are just plain bizarre. For every rapper who'S tried to emulate LL Cool J's "I Need Love" they've wound up coming much closer to his genetically engineered shark memoir "Deepest Bluest." It is with our hands in the air like we care enough to change the station that we bring you rap's most awkward love songs.Big Daddy Kane featuring Barry White - "All of Me" 1990
At the end of the '80s, you could make a strong argument for Big Daddy Kane being the greatest MC of all time. With a unique flow that was somehow smooth and staccato at the same time, a masterful vocabulary and a high energy live show, Kane's legacy was all any rap artist could hope for. There was much anticipation for his
album, and while that Warner Bros budget was spent on clearing some great samples, it also lead to the tarnishing of Kane's public image with the Barry White assisted "All of Me." While we love Barry White and have much love for Kane's previous romantic outings, "All of Me" is just not what we wanted from Kane then and too weird to revisit now. It also holds the distinction for being one of the first videos watched on the first episode of Beavis and Butthead.dead prez - "Mind Sex" 2000
Let me state that I'm not necessarily calling revolutionary gangstas dead prez's 2000 ballad "Mind Sex" a bad song, but revisiting it 15 years later, you have to admit it's really pretty strange. Intended (transparently heavy-handedly) to be an alternative to the vulgar coitus songs that were prevalent at the time (as well as today and during the entire existence of rapping), "Mind Sex" finds the duo discussing how sexy just talking to a woman who can hold a stimulating conversation is. That's cool and everything, but that's not the weird part. The two verses describe the ultimate foreplay: eating a salad, playing chess, sharing poetry, drinking herbal tea and repeatedly reminding someone you don't just want to cram in some intercourse. Hearing a play-by-play account of this, the softest of softcore sex raps, makes for what's aged into a weirdly unique record.Kevin Federline featuring Britney Spears - "Crazy" 2006
Once upon a time, pop princess Britney Spears fell head-over-heels for her back-up dancer Kevin Federline which produced two beautiful children, a reality TV show and Federline's rap career. From his debutPlaying With Fire
comes "Crazy," their duet where Brit explains her love for Kevin. Eerily prophetic in terms of how she guessed that she would be called crazy (and we all remember her 2007), it's really hard to tell exactly what Federline is discussing in his verses. Making "Popozao" sound downright comprehensible, "Crazy" has K-Fed talking about how he's the best, and how he has chest hair as well as a family. This Valentine's Day, if you want to make that candlelight dinner memorable, look into your lover's eyes and coo "Don't think they understand / How much cake the pancake man had."Common - "Driving Me Wild" 2007
Common's made some absolutely incredible music. His albumResurrection
is a masterpiece of the genre, and most recently his song fromSelma
is the best rap song from a motion picture in years. That said, he's had some missteps, the worst of which came from the mid-2000s when it seemed Common was digging for inspiration in the pages ofPeople Magazine
. "Driving Me Wild," a tale of under-appreciated love, or devoted love, or how love changes when you're a celebrity or something, was already dated by the time 2007'sFinding Forever
hit store shelves. With the hook based are his line "Driving herself crazy / like the astronaut lady," a reference you've already rightfully forgotten regarding Lisa Nowak, an astronaut who, while allegedly "Crazy," in 2007 drove from Houston to Orlando in two days while wearing space diapers in efforts to kidnap a U.S. Air Force captain who was romantically involved with another astronaut. Can't imagine a new listener today trying to make sense of it, but let's hope they find a copy ofResurrection
instead.UGK featuring Akon - "Hard As Hell" 2009
When the first UGK single after member Pimp C's death surfaced in late 2008,
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was a curiously tame Akon assisted ode to the curious innocence surrounding those first moments of flirting. Of course, that was the clean version. When the album hit stores and listeners heard the unbelievably juvenile "Hard As Hell," it just killed any sort of crossover cool that the collaboration could have mustered. There's a big drop off between "I want her bad as hell / I'm so ready can't you tell" and "she got me hard as hell / got me pokin' like a nail." In 40+ years of hip-hop, "pokin' like a nail" has to be the most unflattering self-profession of one's erection in the history of the genre. It's just embarrassing to listen to, especially compared to the infinitely more dignified "Hairy Asshole" four tracks earlier.