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The Top 5 1/2 Jaymay Songs by Eric Wolfson

Editors Note:  I’m passing the Major Dudes wand to my pal Eric Wolfson.  A talented musician, incredible artist (if you’re in need of Jimmy Carter painting Eric’s your man) and married to the incredibly talented Annie Crane Wolfson.  I met Eric at one of Annie’s shows and since moving south of the mason dixon line I’m fortunate to call them totally awesome new friends.  This post is the result of Eric asking me if I’ve ever heard of Jaymay — the best singer song writer that no one has heard of.  I hadn’t. 

Back in 2006, I was just another scruffy postmodern Dylan-wannabe kid trying to crack into the NYC singer-songwriter scene that I had read about in all of the Dylan books (SPOILER ALERT: It hasn’t existed since Dylan went electric, as I was soon figuring out). In the meantime, I was going to all kinds of rock shows—such as one fateful evening when I went to Pianos (a Lower East Side music institution) to see the Philadelphia-based indie rock band The Teeth. But then, right when the show was about to start, one of the guys from the Teeth jumped onstage to announce that their friend was going to play a few songs before their set…

1. “Gray Or Blue” (Sea Green, See Blue EP, 2006; Autumn Fallin’, 2007).

I didn’t catch her name at first—& indeed, neither did most of the crowd, since everyone shouted her to repeat it when she mumbled it into the mic—but after two more tries from her side, we learned it was Jaymay. Her guitar was missing a string. She said something about how she didn’t know how to restring it, or something. But when she started strumming on the five remaining ones & began “Gray Or Blue”:


Feel so helpless now

My guitar is not around

& I keep struggling with the xylophone

To make these feelings sound…

But I watched you very closely

& I saw you look away

Your eyes are either gray or blue,

I’m never close enough to say—

But your sweatshirt says it all

With your hood over your face

& I can’t keep staring at your mouth

without wonderin’ how it tastes

& I’m with another boy

He’s asleep, I’m wide awake—

She had me at awake. A girl who can write like Bob Dylan & stack her words like Bruce Springsteen, with the sharp eye of Joni Mitchell & the confessional wit of Liz Phair?

THIS is what I came to New York for.

By the end of the set, I learned “Gray Or Blue” was no fluke. I bought her still-excellent Sea Green, See Blue EP & never looked back. What follows in the post below is 5 1/2 more choice songs by one of the finest living songwriters in America.

2. “Blue Skies” (Autumn Fallin’, 2007).

If “Gray Or Blue” was Jaymay’s proof of her potential, “Blue Skies” is her flat-out masterpiece. Its tagline & mood seem to be lifted from Irving Berlin’s 1926 standard (Al Jolson sang it to his mom the following year in The Jazz Singer), but this is merely an incidental cosmic connection to the greater pop unconsciousness
that only enhances the song’s greater richness & depth.

From the moment the opening drumbeat continues for an unexpected fifth bar (instead of the standard four), unleashing the wash of strings & vocals with the “dah-dah-dah” hook that takes the song to the edge of psychedelic rock without ever crossing into it, this is a recording that exists on its own terms. All of Jaymay’s hallmarks are present—the seemingly effortless vocals, the internal rhyme schemes, the deceptive simplicity of the music—along with my favorite trick of all, the way in which she plays words off each other by drawing one into another (“I prom—mister Blue Eyes I would never be unkind…”).

& on one level, everything described above is just a set-up to be catapulted into one of the most perfect bridges I’ve ever heard, which is at once a contemplation, a work of poetry, a killer returning to the scene of the crime, a temptation, & a dare—not to mention a graduate-level course in melody.

3. “Rock Scissors Paper (Rsp)” (Long Walk To Never EP, 2010).


If people in the outside world know Jaymay, it’s probably from the use of her song “Sea Green, See Blue” in the Season 2 finale of How I Met Your Mother. The star of that show, Josh Radnor, is a big Jaymay fan & asked to use her music for his 2010 writing &
directing debut, Happythankyoumoreplease. Perhaps the best one featured in the film was “Rock Scissors Paper (Rsp).”

“So I have under 2 minutes to sing you this song,” it begins, but rarely have two minutes been used so economically in a pop song. Over the course of 120 seconds, the singer confesses her love, spins a tale about a message in a bottle, & ruminates on the etiquette, moral, & legal implications of plagiarism—all while keeping track of the time (“Now, I have under 50 seconds to finish this song…”), making room for a lovely synth solo, & switching up the dynamics with a clap-along breakdown in the third verse.

Oh yeah, & at the center of it all, she sings the bluntest line like a scrap of overheard conversation that defies the song while summing it up perfectly: “Really, who cares how they feel?”

4. “Corduroy” (Sea Green, See Blue EP, 2006).

A love-letter to NYC open mic performers & the late-night trains that take us away from them. As a song, pure melody; as a production, pure beauty.

5. “One May Die So Lonely” (A Long Walk To Never EP, 2010).

3 minutes & 37 seconds of voice & guitar, straightforward strumming & matter-of-fact singing, delivered in a second person narrative. In terms of delivery, “One Might Die So Lonely” may be Jaymay’s finest vocal, brimming with confidence, clarity, & humor (just listen to the way she twists the line “little old man”).The song is the rare stream-of-consciousness narrative that feels as coherent as a set story, with the singer searching for words, building off of them one another, stitching together snippets of conversation with thought & explanation.That’s all well & good, but I would include “One Might Die So Lonely” on this list if only because of the line delivered towards the end:

It just gives me hope

Like music is a rope

To hold you right here

As far as I can tell, therein lies the power of songwriting & listening to music, summed up in three lines or less.

5 1/2. “40 Hours Ago” (Single, 2011).

When Jaymay made her catalog available for Josh Radnor’s
Happythankyoumoreplease, it provided the perfect outlet for songs like this—one-minute, half-song sketches that play like demos with a raw honesty that would far outstrip any “finished” version that might try to complete it.

“40 Hours Ago” is one of Jaymay’s best of these short songs—it contains a confessional vocal, a lovely melody, a playful lyric filled with internal rhymes & her signature word- connecting (“What did you come here for—ty hours ago, I was feeling one way…”), an understated production that shrewdly lines up the piano key with a doorbell ring, & a direct intimacy that doesn’t let up after multiple listens.

In terms of length it may only be half a song, but in terms of content it’s an executive summary of the signature hallmarks that make Jaymay a masterful songwriter. But all that said about Jaymay, there is one element to her music that for me trumps all the rest: The rare & elusive ability to create a song that sounds like it simply has always existed. Her music walks the line between the old & the new, the forgotten & the remembered, the might-have-been & the never-was. This is what stopped me cold & made me listen on that New York City night all those years ago—& it is what has kept me listening ever since.

My good friend from majordudes asked me to do a guest blog on one of my favorite artists, #Jaymay! Hope you dig.