Here’s the funny thing about Kind Of Bloop: it’s not funny.

When I first heard that Andy Baio (the author of blog Waxy.org) was producing a chiptune version of Miles Davis’ Kind of Blue, I grinned.  Who wouldn’t be curious to hear the rigid, retro chirps of chiptune jabbing at such a sensuous, cool classic?  The official site calls it a “blasphemy,” but they’re just being cheeky – after all, this is no tackier than Miles himself covering Cyndi Lauper’s Time After Time. But it sounded like a great gag.  Heck, it could even be funnier than a uke and kazoo duet of Bye Bye Blackbird.

But after a few spins, I realized there’s more going on here than a gimmick.  So I looked for an expert opinion. I contacted musicologist and radio personality Dr. Demento, America’s leading expect on novelty songs.  He had heard the previews, and he took Kind Of Bloop seriously.  “It's a novelty, but to me it's not funny the way Weird Al, or Richard Cheese with his lounge-lizard versions of alternative rock hits, is funny.”

The performers sound like they agree.  As Virt (nee Jake Kaufman) wrote on the album’s page at Waxy.org, “Way I see it, chiptunes can either be a punishingly difficult artistic medium we happened to grow up with, or a tired retro fashion statement. Our goal was to stick to the former, pushing the limitations hard, building on our capacity for expression using the most basic sounds. There could be no better challenge, Andy thought, than one of the most expressive jazz albums of all time, one that has inspired us all.”

You could infer a manifesto: that the album sets out to prove that chiptunes is not only a legitimate musical style, but that it can even handle the greats.  The thing is, that’s not exactly what Baio and the artists have said.  And the album doesn’t make the case.

Ast0r’s So What keeps the dignity of the arrangement and follows the solos note by note.  Sergeeo’s Blue And Green also plays it safe.  And as for Flamenco Sketches – well, I don’t envy Disasterpeace having to tackle one of the most beautiful performances ever set to tape, but going for a jazz fusion feel with George Duke-style keyboards is a little kitschy.  But it’s not as kitschy as Freddie Freeloader, which starts fun and frisky and then goes over the top looking for more tops to go over.  The arrangement gives you a department store full of ‘80s Casios all jamming at once, and on the solo it  sounds like Virt slammed all his presets to “YOWZA!!”

But then there’s Shnabubula’s All Blues, which is modern, and energetic, and brilliantly spastic.  Shnabubula totally sides with Mario over Miles - dig the sweet combo he picks up at the two minute mark – and he crafts fresh settings and beats for the solos, building to a breakdown that’s garish and wicked awesome.  It’s the only cut on the album that tackles the source with the invention it deserves.

When I asked Dr. Demento about the lineage of the work, he said, “I'm reminded very strongly of Isao Tomita's synthesizer arrangements of classical pieces that were so very popular in the 1970s and 80s. I gather that the technical processes involved here are quite different from what was going on with Tomita (or Walter/Wendy Carlos) but the effect for me is about the same.”

Kind Of Bloop has plenty in common with that older synthesizer music: it’s laboriously constructed by fanatical artists out to push the limits of their tech.  But in the 60s and 70s, electronic musicians were still dreaming of how far they could take a Moog, and how serious an instrument they could prove it to be.  Kind Of Bloop lacks that ambitious futurism, and the technology it showcases is just one more tool in an electronic musician’s kit.  Kind Of Bloop is an ambitious pastiche, and it chews through an impressive swath of electric, electronic, and improvised music.  But it’s a novelty record – because for the most part, it puts an old spin on the familiar instead of melting it into something new.

Summing up his take, Demento told me, “I'd say it is fun and neat for its own sake.”  But did he like the covers?  “They're nice to hear, but I think I'd enjoy hearing So What no matter what instrument it was played on.”

Chris Dahlen writes about games, music, pop, and tech. You can find him online at @savetherobot, or drop him a line at chris[at]savetherobot.com.