“Where should I go?"
"That depends on where you want to end up."
― Lewis Carroll, 'Alice's Adventures In Wonderland & Through the Looking-Glass'

I don't do well with formatted music, regardless of whether it is terrestrial radio or a  streaming service that tries to predict what I want to listen to. The problem doesn't lie with those channels, but with me: I don't know what I want to listen to most of the time. I just want to listen.

I have 36,584 songs in my iTunes library today, beginning alphabetically with 'A-OK' by Face to Face and ending with 'Zydeco Honky Tonk' by the great Buckwheat Zydeco. (Technically the last song in my playlist is Outkast's '?', but let's just stick with the alphabet.) According to iTunes, I can listen to music for 102 days and never repeat a song, provided I count my 17 different versions of 'Ziggy Stardust' as individual songs.

And that's just the digital me. Then there are the shelves crammed full of vinyl, with more of both streaming in every day: new music, b-sides, imports, out of print albums, the odd gap filler. I know I'll rarely spin 'Seventh Star,' for example, but without it there's a hole in my Black Sabbath collection. That's like a rock in the shoe of a record geek, or a fly in the Vaseline if you're a Stone Temple Pilots fan.

What do I want to listen to? All of it, and right now, but that's not possible so I need some path through my musical forest. "Shuffle" is okay, but with a diverse library it can be a bit jarring, swinging between moods like my Aunt Edna when she's off her meds. No, the best option is to just follow the music down whatever rabbit hole it wants to take me.

The path from one song to the next isn't always clear to me, but with a little thought I can determine how I got from here to there. It's like a game of Six Degrees of the Bacon Brothers.

For example, this afternoon I started with 'Crazy Blues' by Mamie Smith & Her Jazz Hounds. Talk about a deep cut: The song dates to 1920 and is often cited as the first blues record. It's pretty clear where I'm headed from here -- straight to Ray LaMontagne.

Wait, that's not clear at all. The Black Keys maybe. Jack White, sure. How the hell did I get from a 100-year-old cut to a completely unrelated contemporary artist? It takes me a second to figure out what happened, but 'Crazy Blues' evokes an era when men wore hats, and I just happened to cover a Ray LaMontagne gig recently at which he sported a felt hat.

And so from Mamie Smith I'm off to LaMontagne's 'Supernova' and its glorious opening track, 'Lavender.' Everything about this cut works for me: the lyrics, the production, the instrumentation, the faux-psychedelic "chick-ah":

LaMontagne's is the soothing variety of neo-psychedelia, very lush and relaxing. I love that, but I also like the more freaked brand of psychedelia.  I switch over to King Gizzard and the Lizard Wizard, an Australian band that blew me away at this year's Northside Festival in Brooklyn. These guys go at it hard. Proceed with caution if you have any chemicals lingering in your bloodstream:

From there it's a quick leap to the last great psychedelic revival, the Paisley Underground movement of the early '80s. The Bangles were the breakout success, but so much great music came out of that scene: the Three O'Clock,, Dream Syndicate, Game Theory, Rain Parade.

The latter's 'Emergency Third Rail Power Trip' is essential listening for anyone who digs LaMontagne's 'Lavender.' The out of print vinyl will cost you some bones, but both CDs and downloads are still available at a reasonable price. 'I Look Around' is the cut that lands on compilations (three copies in my iTunes library), but for my psychedelic dollar 'Talking In My Sleep' is the tastiest cut on the record:

Thanks to the Rain Parade, I'm now thinking about both psychedelia and rain, and so down the rabbit hole I tumble to the Beatles' 'Rain.' Released in 1966, this b-side sits almost directly at the chronological fulcrum point separating Mamie Smith & Her Jazz Hounds and LaMontagne's 'Lavender.' That's right, I said b-side. The Beatles were so damned good that they essentially created psychedelia on the flip side of 'Paperback Writer.' This track wasn't available on an album until 1970's 'Hey Jude':

And there it is: Mamie Smith to the Beatles in five moves, courtesy of Ray LaMontagne's hat.

Music finds its own route through our minds, tying memories and emotions together and cleaving apart the strict genres of programming.

Music finds its own route through our minds, tying memories and emotions together and cleaving apart the strict genres of programming. It doesn't care how new or old a song is, or whether it's approved by the cognoscenti. All that matters is that the playlist you're listening to right now is the playlist that you should be listening to right now.

Just let it happen. Close your eyes, press "play" and tumble down the rabbit hole. You never know where you'll end up, but wherever you land will be where you were meant to be.