"Irony is for b*tches, I'm down for Byrony, fools!"

Long before Journey's Don't Stop Believing became a posthumous cultural touchstone widely embraced without apologies, trumping VH1's snarky and false nostalgia with an appreciation that the song's genuine emotional resonance couldn't have been achieved without the grandiose pomposity of Steve Perry's high notes, there always had to be some kind of Foucault level deconstruction of one's emotional responses before someone could just stop fronting and say they like a song, with some petty stab at preserving dignity with the punch line of it being a guilty pleasure. Rappers on the other hand seem to have been entirely out of the loop on other people's musical hangups, and in their record bin scouring seem to have digested pop culture wholesale with no regard to a song's perceived connotations.
For all of rap's macho posturing, and self-concious sexual identity crises, rap has embraced some of the flat out gayest (by arbitrary cultural associations, because who in 50 years will know why the hetero male guard deemed them as legitimate acid tests for possible dwellers in the invisible closet, what a strange concept that will be in a few hundred years, no?) songs and made them worthy of any street aficionado. When an album's beats fail or a rapper goes in a direction to his audience's dislike, it's considered an artistic failure, and a creative deficiency that demerits that rapper's good will. But in some senses it is absolutely liberating that a rapper doesn't hold to the same standards of legitimacy and doesn't have to say some shit like "it's so bad it's good" in order to get down with Spandau Ballet. While in some instances there might have seemed to be a friction between rappers and r and b singers that was revealed to be nonsense, as even the most hetero, testosterone pumped caricatures let smooth croons grace their supposedly graceless tunes.
Here are some of my favorites.

Method Man featuring Blue Rasberry - Release Yo' Delf.
Please watch: Actual video, embedding disabled by request of universal music group. Songstress front and center, then Meth owns it.
As pop culture history would tell it, this song is a gay torch carrier. As Method Man would tell it, it is both a bona fide hood anthem and a salute to anyone able to navigate the treacherous international waters of the record industry. The lyrics are I will survive, sculpted with a little street vernacular those three words are as straightforward as they can be.

Z-Ro - Continue 2 Roll (ft. Tanya Herron)

Yes! Another context in which I can laud Z-Ro for being so painfully earnest that his usage of a spandau ballet song as a triumphant glare in the face of morally dispiriting adversity is as touching as he intended it to be, and nowhere near as schmaltzy as it sounds like it could be. He makes keen societal observations about the hypocrisy of the media's racially charged representation of rap culture, the onslaught of crime and violence and the crumbling of any kind of sustainable, benevolent infrastructure, and is generally depressed as hell about all of it. It works, and you can bet he didn't think twice about whether the sklar brothers would think it was funny because I Love The 80's made fun of it.

Crime Mob - What is Love

A possible cry for help after sleepless nights playing hopscotch in debauched night club orifices (gender neutral), the song was turned into a novelty joke scoring the failed endeavors of the brothers butabi on an SNL sketch about obnoxious club patrons who don't know when to accept a rejection on the dance floor, or anywhere else for that matter. Crime Mob completely avoided the song's essentially cheese whiz associations and took it for what it immediately sounds like. A serious contemplation on the query put forth in the song's title. When asked about taking the song's sad impressions at face value by Status Ain't Hood, Crime Mob went into flat out braggadocio and said that if you don't like something, they'll flip it 'til you love it.

Cam'ron - Girls

Sampling a carefree bubblegum self-indulgent girlie-girl anthem Cam was going for one of two things. The first, Cam measured and acknowledged a genuinely good pop song when he heard one, and realized it would make a great foundation for a song. Two, he measured twice and realized the song's a post-feminist ideation of anti-intellectual girlie-girlism and would make an excellent self-defeating casemaker for Cam'ron's justification of womanizing, essentially boiling down to "Girls are all whores". Either way, dude sampled Cyndi Lauper into a chauvinist anthem.

Beanie Sigel - Wanted

Was it hair metal's most enduringly awful sons? Because it's definitely not the hard rock wikipedia claims it to be. Bon Jovi, coif in tow, stool down low, acoustic guitar for show, inevitably as empty as a midnight laser show, grabbing for archetypal glory by way of a western cliche. Beanie Sigel, though, takes the song's theme, and uses Jovi's wail to maximum effect, their siren like grip a stimulus for his near panic attack, as he fretfully recounts the down side of being an outlaw, on the run from the cops. Once the initial joke wears off, and before Cam'ron blazes in nuts first, this is a fairly intense song.

Billy Squire's The Big Beat in Jay-Z's 99 Problems and Dizzee Rascal's Fix Up, Look Sharp

(This was so much fun to shout during Rascal's set)
Okay, and a bunch of other songs reaching back past Big Daddy Kane but I'm more familiar and comfortable with these two, and only somewhat surprised by its overall popularity. That two hard rappers would reach back to what signaled the rise in arena sized softies, crying pelvises known as def leppard, poison, air supply and various other fashion accessorizing boutique stylists with a penchant for leather is further proof that rappers don't need something hard in order to cultivate a suitably unfuckwithable image. Seemingly, both Jay and Dizzee recognized the cock in the rock and ran with it. One using it as a backdrop for a defiantly reactionary song about racial profiling, and the other, to, well, fix up and look sharp. I'll be honest, though, this original song is pretty badass. It's also instantly recognizable in it's sampled form and therefore posting videos of its newer contexts is unnecessary.

Kanye West - Good Morning
Though he samples Steely Dan on the next track and daft punk on the third, there's something precarious about the usage of elton john in light of Kanye's public discussion and disavowal of homophobia, and both preceding and subsequent epithets targeted at him because apparently all rappers have gaydar. This probably has nothing to do with the above and has more to do with this being a good song, but still, I'll throw some political context to heat things up.
Original song- Elton John: "Somebody Saved My Life Tonight"


Bonus: Though it's only mimicked in the way his name is announced, you know that Method Man and the Wu totally sat through this song and thought they could make that sound tight as fuck.
Guess which song this ended up in.