I figure that today is just a good a day as any to discuss this, especially since he's appearing on the XXL Freshman Cover this year. Almost a year ago, I dropped a piece here detailing my disdain and/or "sadness" towards Lil' Dicky's brand of hip-hop. While I enjoyed his wordplay, I found his music childish, full of not-even-remotely-ironic "dudebro" tropes, and just reliant on his whiteness (and putting over of said whiteness to bask in its white glory). I even went as far to call this man, whom I didn't know from a hole in the wall, an "elitist piece of shit."
Harsh words, am I right?
However, I decided to give Dicky another chance after a commentator on this here site called me an "idiot" and I got a couple DMs about how biased my take on Dicky was. Never the one to be called biased (them's fightin' words 'round these parts) or an idiot and not do something about it, I dove back into Lil' Dicky and his music, especially prompted by a song he did with Jace, "Oh Well," from the Professional Rapper album.
All in all, I found myself less "social justice warrior angry" about Dicky being a White guy in a world of usually non-White rappers and about him teaming up with Fetty Wap. I still side-eyed him on some of his seemingly un-ironic misogynistic and racially-awkward bars (but, truth be told? That's sometimes hip-hop in general). But, for the most part, I found myself, even though I probably shouldn't have, since I'm, apparently, "biased" against him, enjoying the fuck out of his music and saying "well, I knew he had bars. But, he's kinda got BARS!!!! too."
I also found myself realizing that, maybe, I was biased against Dicky because of all the negative energy surrounding the past couple years with relationships between White folks and non-Whites (read: stuff like what went down with Trayvon Martin, Tamir Rice, Oscar Grant, etc.). While Dicky raps from a place of love (even with some of his ironic lines being on some eye-raising, "you can't do that, bruh" shit), I sometimes saw it more as "RAWR HE'S A WHITE MAN WHO'S INFRINGING ON NON-WHITE PEOPLE'S EXISTENCE."
Ladies and gentlemen, that's a bullshit, stereotype-heavy way of thinking. While I'm not going to hop on any apologist bandwagon, you do have to realize that not all people of a certain group are intentionally trying to infringe or overtake. When you think like that, when you get on that level, you're no better than the folks you're trying to chastise.
So, to Lil' Dicky, my bad.
Getting back into the music, I think that Dicky's strengths come from the fact that he's organic. He knows that, as a former ad executive, he doesn't really "belong" in the rap game. And, yeah. Dicky does have those moments where he looks like that random White guy you see at a Bone Thugs concert rapping every word (aside from "nigga") better and more hype than most of the non-White audience members. However, it comes off more as realism wrapped in self-depreciating parody than it does malicious. Plus, again, he can actually drop some bars.
For examples of this sort of thing aside from Dicky, think Lonely Island with some heavier bars, or think Asher Roth before--and after--folks tried to pigeonhole him as just a "college rapper." They know they're White. They poke fun at this whiteness in a way that, if you're not careful, can start to go left, real fast. However, it never really goes there in a way that's worthy of raising pitchforks and chasing them down the streets.
Does Lil' Dicky "deserve" his XXL spot? I mean, there are far worse choices. Besides, the guy, aside from his music, organically kind of just sprung up and did what he's done. Plus, as far as I know, he's a legitimately indie artist. So...