When the Guys Behind ‘Yacht Rock’ Took Aim at the Humiliating Practice of White Musicians’ ‘Try-N-Raps’

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Pod-Canon is an ongoing tribute to the greatest individual comedy-related podcast episodes of all time.

About a decade ago a group of friends turned their affection for the super-smooth, hyper-produced, polished pop perfection of the late 1970s and 1980s into a cultishly adored web series called Yacht Rock after their homemade name for music made by, for, and about wealthy, hirsute white men who own expensive boats and make said boat ownership the cornerstone of their carefree lifestyle.

The idea was to provide a secret history behind some of the sleekest hits of the Carter and Reagan era, to expose the seedy underbelly, feverish competition, out of control egos and deeply unflattering hairstyles behind upper-middle class anthems by the likes of Hall & Oates, Toto, Michael McDonald, and their ilk.

The humor came from imagining these aggressively unthreatening pop stars embroiled in comic-book-style conflicts with other aggressively unthreatening pop stars as well as from dreaming up a wonderfully specific universe for these half-remembered hit-makers from the whitest recesses of our cultural past.

Underneath the web series’ smart-ass irreverence lies an underlying respect for the musicianship and smooth (if sometimes soulless) mastery of the cornball pop stars they’re spoofing. Nobody devotes that level of time and energy to something unless they love it on some level. Accordingly, the men behind Yacht Rock came to honor the hyper-processed pop of the late 1970s and early 1980s more than they came to bury it. Hell, by giving Yacht Rock such an infectious, appropriate and strangely lasting title, they were engaging in pop music criticism as much as they were goofy comedy.

It is a critic’s job to ferret out trends and themes in pop culture, to provide a cultural context for art and trash that endures. That’s exactly what the gents of Yacht Rock were doing; they were taking a lot of smooth music from the semi-recent past (smoothness seems to be the defining quality of Yacht Rock; without it, music is canoe-worthy at best) and created a name for it so perfect it defined a whole style of music instantly.

The Yacht Rock ship sailed a while back but the men behind it have drawn upon their gifts as musical anthropologists to launch Beyond Yacht Rock. As the title suggests, the podcast is both rooted in the mindset that created Yacht Rock but also devoted to exploring and charting new waters.

The Yacht Rock gents might not have created a new sub genre with Yacht Rock, but they indelibly identified and more importantly, titled one when they gave the world the Yacht Rock concept. On Beyond Yacht Rock they do the same thing with other strangely specific mini-genres you might never have thought about but they, thank goodness, thought about way too hard.

The men occasionally touch upon their beloved Yacht Rock. They have a brand to protect, after all, but instead of exploiting their semi-famous brainchild, they’re finding new, Yacht Rock-like sub genres and sharing the top ten songs in each of them. The podcast hit the ground running, and has so far explored such mini-genres as “Sultry Hits,” “Bald Metal” (hair metal should-be-hits), “These Guys Probably Fucked” (songs where the singers “probably engaged in making the beast with two backs together”) but my personal favorite is the podcast’s second episode, “TRY-N-RAPS.”

The criteria for TRY-N-RAPS is simple: it collects songs from prominent artists (or, alternately, Bart Simpson) who became famous for performing a non-rap form of music, yet nevertheless felt weirdly obligated/entitled to try rap all the same, despite a widespread dearth of both what the young people call “skills” and also “authenticity.”

There’s something weirdly condescending, even ambiguously racist, about these songs. Implicit in these sad stabs at cultural relevance is the myopic, mistaken conviction that everyone can, and should try their hand at rap because it’s just so easy. It’s just making rhymes over a beat, right? Anyone can conceivably do that, from Fred Flintstone and Bernie Rubble in a Fruity Pebbles jingle that is referenced here as an unexpectedly seminal moment in the white, mainstream co-option of hop hop, to the sassy grandma from The Wedding Singer who is hilarious because she’s white, and old, but she’s rapping all the same!

The list the gents have come up with illustrates in no uncertain terms that no, not everyone can rap, and it’s pretty ignorant to feel otherwise. Not everyone should rap, particularly the ten non-rap-wizards whose earnest fumbling they have helpfully collected into handy list form.

Part of what makes Yacht Rock the web series and Beyond Yacht Rock so much fun is that the people behind it genuinely know, understand, and love what they’re talking about. Hell, the “Van Halen v. Van Hagar” episode, which pits David Lee Roth’s Van Halen with Sammy Hagar’s version, is heated in only a way a podcast involving people who’ve thought way too hard about the music of Van Halen can be.

But there’s nothing academic about the way Beyond Yacht Rock approaches music. The vibe is less professorial than a couple friends who love music obsessing about pop’s past over a couple of cold ones.

Some of the artists chronicled on the “TRY-N-RAP” podcast are bona fide legends, like Stevie Wonder, Joan Jett, Brian Wilson, and Lou Reed, but that somehow didn’t keep them from somehow imagining that they had any place in the hip hop landscape, even as a misguided dilettante.

The podcasters draw a line between pre-NWA and post-NWA try-n-raps; they argue that before NWA try-n-raps were more forgivable because hip hop was still seen as a kooky novelty, a silly fad the young people enjoyed but that would burn itself out, and post-NWA, when it became apparent that hip hop was an important cultural movement, and not just some teenybopper craze.

Try-n-raps are generally the product of people who are overwhelmingly white, overwhelmingly middle-aged or older, like Lou Reed, whose “Original Wrapper” cheekily references his O.G status as a man whose talk-singing in The Velvet Underground marked him as something of a proto-rapper, at least by his own estimation. But there’s a big difference between singing in a style that vaguely resembles rapping and trying your hand at the real deal, and “The Original Wrapper” needs to be heard to be cringingly disbelieved.

Equally cringe-worthy and morbidly fascinating is the literal-minded nature of these hippety-hop ripetty-raps; many of these dilettantes felt the need to put the word “Rap” or “Wrap” to illustrate that they’re straying from their home turf and, as the young people sadly no longer say, getting jiggy with it. They also note the preponderance of Try-N-Rappers who employ the “My name is () and I’m here to say” paradigm employed by old school rappers, fake rappers, and faux-rappers alike.

Country-rap, punk-rap, cartoon rap (O.G rapper Bart Simpson is representing for his Springfield peeps), California-surfer-rap, wrestler-rap: the Beyond Yacht Rock gang explores a wide array of hip hop mutations that all have something in common: the folks dabbling with rap have no business doing so. The results are notable mainly for surreal miscalculation. These artists may be trying to honor hip hop by trying their hand at it, but they accidentally end up insulting it instead. In recreating rap in their own image, they end up dishonoring both themselves and hip hop.

These raps may be a crime against music, hip hop and good taste, but separately and collectively, they provide a fascinating window into the way hip hop has been abused and mistreated by a podcast that is still young but shaping up to be a smoothly consistent pleasure, for music obsessives and schadenfreude enthusiasts alike.

Nathan Rabin is the former head writer of The A.V. Club and the author of four books, including Weird Al: The Book (with “Weird Al” Yankovic) and, most recently, You Don’t Know Me But You Don’t Like Me.

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