Fans of Childish Gambino can be split in to two groups: those who like hip hop and appreciate his wordplay, and those who use the phrase "I don't normally like hip-hop but..." before admitting that they just happen to like the guy from Community a lot. That he's a strong enough on the mike to gain the appreciation of the first group without alienating the second is a testament to his abilities.
On his new mixtape, Royalty, Gambino made the controversial decision to actually work with other MCs. It was a risky move for a guy who got his rap name from the Wu Name Generator to rap with RZA, and one that could alientate some fans. Those in the second group who didn't like the hip-hop guest appearances had their patience rewarded with one they knew was geared specifically toward them: Tina Fey.
There are those much smarter than I who would say the use of Fey was a commentary on the nature of hip-hop skits; they'd probably use the word paradigm somewhere. For me it was just a reminder of some of my favorite guest appearances by comedians in hip-hop's past. And while Fey saying "racks on racks" is funny, it's not quite as good as what some other comedians have brought to the table.4. Kevin Hart & T.I. "Fuck a Mixtape"
While 2012 may be the year that Kevin Hart becomes a household name, he's a comedy veteran who's been around for years. In 2010, T.I. was fresh out of jail and dealing with a whole mess of people who were telling him to ignore the mixtape game and focus on putting out a real album.
He wasn't having any of that, and to really drive the point home he hired Hart to be the voice of those who had argued against him. What had been annoying in real life turned in to something hilarious.
Most people will focus on the end of the skit where he goes through the long series of people he has to say "fuck" towards, including himself, but for my money the best joke in the one he gets off right at the start. There are few descriptions of T.I. that are as accurate as "Long Face, Skinny Body." Sometimes a good insult is the best comedy.3. Dave Chappelle & The Roots, "In Love With The Mic"
How cool are The Roots? The Roots are so cool that they had one of the biggest comedians in the world guest on a song and then made it a bonus track.
2004 found both parties at an interesting point in their careers. The Roots were critically loved but years away from their Jimmy Fallon gig that would finally get them the fame they deserved. Dave Chappelle was at the height of his career due to Chappelle's Show but only a few months away from when things would all go south.
While he doesn't say a lot on the track, there's a certain infectious energy that comes from Chappelle as he sings along to the hook. Given the amount of screen time The Roots get in Dave Chappelle's Block Party it's clear he's a huge fan and that comes through on the track. Plus, the idea of him cutting a $100k check because he didn't get it on the first take is pretty funny.2. Eddie Griffin & Dr. Dre, "Ed-Ucation"
There are a lot of guest appearances on The Chronic 2001. We're talking legends, heavy hitters, and some guy named Hittman. But at 23 tracks, there is a lot of dead weight and whole mess of throwaway skits padding out the run time. It's as if Dre was throwing everything he had recorded at the wall and hoping for the best.
By 1999, Eddie Griffin was a veteran in the world of Southern California hip hop skits. While his first appearance on the album ("Bar One") is better forgotten, his turn on "Ed-Ucation" is one of the more memorable bits of the album.
"Ed-Ucation" is, at its core, a rant against materialism delivered in Griffin's unique and colorful style. It's also insanely quotable even if they're quotes many of the listeners would never be able to say out in public. Although he may be hyperbolic, the man makes a good point: Whatever happened to falling in love with someone who uses public transport?1. Chris Rock & Kanye West "Blame Game"
"Blame Game" is an epic that includes an Aphex Twin sample, John Legend crooning, and Kanye reciting a poem. It's a patchwork quilt that only Kanye would construct. While most rappers are content to include skits seemingly at random, Kanye makes Rock's appearance part of the greater narrative of the song.
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That's great and all, but it would have been all for naught if the skit was awful. Not only is it not awful, it delivers arguably the most well-known moments from the album. It's also provides some much needed levity after the heaviness of the previous five minutes.
Whether it was making "Yeezy taught me" something girls of questionable morals would quote on their Facebook accounts, making Twista's watch one of the most famous accessories in hip hop history, or just had us all threatening to shoot a bootlegger, Kanye and Rock manage to turn one of the darkest moments of the record in to something completely different while keeping it in context at the same time.