The Top 5 1/2 Jaymay Songs.

(Note: This article is a slightly adapted version from Beth Silverman's totally awesome music blog, Major Dudes. Do yourself a favor & check it out.)

Jaymay, c. 2006.

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 the Dylan books (SPOILER ALERT: It hasn't existed since Dylan went electric, as I was soon learning). 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 (now dearly-departed) Philadephia-based 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 2 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 then she started strumming on the 5 remaining ones & began "Gray Or Blue":

I—

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 rhymes like Bruce Springsteen, with the sharp eye of Joni Mitchell & the confessional wit of Liz Phair?

THIS is what I had come to NYC 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 is 4 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 the proof of Jaymay's 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 5th bar (instead of the standard 4), 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 setup 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 is "Rock Scissors Paper (Rsp)."

"So I have under 2 minutes to sing you this song," it begins, but rarely have 2 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-&-whistle 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 just voice & guitar, straightforward & strumming & matter-of-fact singing, delivered in a second person narrative. In terms of delivery, "One Might Die So Lonely" may just be Jaymay's finest vocal, brimming with confidence, clarity, & humor (just listen to the way she twists the words "little old man" or breathes life into the line "I really think you're crazy"). The song is the rare stream-of-consciousness narrative that feels as coherent as a set story, with the singer searching for words, building them off one another, stitching together snippets of conversation with thought & explanation.

Now that's all well & good, but I would include "One Might Die So Lonely" on this list if only because of the line delivered to the singer's long-lost companion 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 3 lines or less.

5 1/2. "40 Hours Ago" (Single, 2011).

When Jaymay made her catalog available for 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 the best of these short Jaymay songs—it contains a confessional vocal, a lovely melody, a playful lyric with 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 keys 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 Jaymay's signature hallmarks.

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 NYC night all those years ago—& it is what has kept me listening ever since.