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It’s OK to Laugh at (or Even With) Lil Dicky

The rapper’s latest single, “Freaky Friday,” sees him leaning all the way into his Lonely Island potential—and, frankly, it works

Lil Dicky has been laughing at himself for years. With his quasi-crude, cheesy sense of humor and deeply normcore aesthetic, he’s not your average rapper, so there’s always been a wealth of evidence for why you should probably hate the guy. He is a man who has built an entire rap career on the premise that, well ... that he’s got a small penis.

DICKY WE MADE IT OMGMGMGM @kevinhart4real

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Since his 2013 hit “Ex-Boyfriend,” which garnered more than 33 million views on YouTube, Lil Dicky has committed himself to the lane of being a comedic rapper—sort of like Andy Samberg, if he took #bars seriously. The move has been a successful one, depending on how you define success. He’s consistently proved he can clean up on YouTube (2015’s “$ave Dat Money,”’ featuring Fetty Wap and Rich Homie Quan, racked up more than 84 million views), but he’s never earned any credibility as an artist. The opening lines from his 2013 video for “Sports” suggest why: “There’s three things I know about, man: sports, soaking up female genitals, and rap.”

But Dicky may be turning a corner here, or at least demanding a modicum of appreciation. On his latest single, “Freaky Friday,” which dropped Thursday and features Chris Brown, the rapper delivers the same brand of self-deprecating, silly humor, but he undercuts it with just enough self-awareness that it avoids the same pitfalls that make some of his older work corny and easy to ignore. After years of tinkering with his formula, the 30-year-old rapper from Pennsylvania has perfected his product: broad, low-hanging bro humor delivered via inspired song (and video) concepts and technically proficient rapping. The comedy is not sharp, but it’s undeniably entertaining.

In the opening of “Freaky Friday,” American Vandal’s Jimmy Tatro (who knows a thing or two about dick jokes) sums up the general public’s opinion of Lil Dicky in his description of him to his date: “He’s not like a rapper, rapper, he’s like a funny rapper. He raps about how small his dick is. ...You thought he was like a rapper? No, no, no. Yeah, he knows.” Lil Dicky reacts to the (extremely) backhanded compliment with the blankness of a man who’s heard it a million times:

Lil Dicky Dirty Burd Inc.

Chris Brown, on the other hand, has his issues, but his brand embodies everything that Lil Dicky’s does not: He’s a talented singer and performer with undeniable swagger. Casting Brown as his counterpart in a body-switching scenario—which, spoiler alert, is what happens, if the song title wasn’t a big enough hint—allows Dicky to both play out his greatest fantasies (being a good dancer, having women draped all over him, and, most problematically, being able to use the N-word) and self-deprecatingly lean into his utter lack of charisma and big-time success.

Lil Dicky sitting up in bed Dirty Burd Inc.

The video is just as much a comedy skit as it is a rap song, a concept popularized and perfected by the Lonely Island. Case in point: In the same way Samberg’s group used starpower as a punch line—casting Jessica Alba and Blake Lively in “I Just Had Sex”—so too does Dicky, closing out “Freaky Friday” with some great assists from Ed Sheeran (whose perfect cameo almost makes up for that time he popped up in Westeros), DJ Khaled, and Kendall Jenner.

DJ Khaled Dirty Burd Inc.

While Lil Dicky is still fishing for the same easy laughs that he has been for years, he is now going all in on the kind of satirical rap that has earned groups like the Lonely Island, or even Weird Al Yankovic, a legitimate level of respect. Frankly, it works. He’s not going to be up on the Grammys stage performing alongside Kendrick Lamar anytime soon, but he’s always known that, and we’ve always known that. Don’t be mad at Lil Dicky—just enjoy the bad jokes.