“In case you aren’t autistic, we’re doing this set in alphabetical order,” Stephin Merritt paused between songs to tell the audience, gathered at City Winery on the first truly cold Saturday evening of the season a couple of weeks ago. Artistic? I mouthed at my companion. Autistic, he mouthed carefully back.

This bewildered, comical exchange is somewhat exemplary of Stephin Merritt and the kind of music he makes. Unassuming, in casual clothes and a newsboy cap, with an unwavering deadpan, he glides so seamlessly between the offbeat, the blasphemous, the twisted and the unapologetically sentimental that laughter often comes a beat late, preceded by a double take and a, “wait, what?” Yet the truest measure of Merritt as a brilliant songwriter is his meshing of these varying states into one uniquely complex artistic persona– bitter and gleeful, enjoying himself and wishing he was anywhere else—which came out in full force at City Winery for a rare, sold-out solo show, part of a one or two-off continuation of his tour this past spring.

Merritt is perhaps best known for his work as the lead singer/songwriter of the Magnetic Fields, whose three-disc concept album, 69 Love Songs, cemented their cult status and landed them a spot on Rolling Stone’s 500 Greatest Albums of All Time. By choosing to play his set alphabetically- one song beginning with each letter of the alphabet- he not only took the audience through a career spanning set, but reminded the audience what a prolific (albeit quirky) songwriter he truly is.

Every song received an introduction, as he seemed more than happy to share anecdotes about the songs’ origins, from watching Oprah, to drinking too much gin at the Danceteria as an NYU student. But by far the best anecdote of the evening was when he leaned into the mic and introduced one of my favorite tunes of the evening, “Josephine,” with no detectable shred of arrogance – but no humility either – “I improvised this song into a tape deck at the age of 15.”

A longtime fan, I delighted in the rarities that the set unearthed, from a song he wrote for the score of the Off-Broadway production of Neil Gaiman’s Coraline, to one gem “Shipwrecked With You,” from his work with the Gothic Archies, a side project that put out only one record, The Tragic Treasury, with a track to accompany each audiobook from pal Daniel Handler’s (Lemony Snicket) deliciously dark Series of Unfortunate Events.

From the Magnetic Fields, Future Bible Heroes and the 6ths, to the Gothic Archies and his own solo work, Merritt had any number of projects to pull from, and it seems he hasn’t ceased his irreverent creation in some form or another for close to two decades. In production with certain projects, tracks are spruced up with electronic layers and more complex instrumentation, and with the Magnetic Fields many songs are performed by Claudia Gonson. But for this evening, Merrit was accented sparsely by his own ukulele and his Magnetic Fields bandmate Sam Davol on cello. His unmistakable, plaintive baritone took center stage, and the wellspring of this magnetic, undeniable creativity was clear. In “I Wish I Had An Evil Twin,” he sings, “I wish I had a very bad and evil twin to do my will/to cull and conquer, cut and kill/just like I would if I weren’t good.” Merritt encompasses both twins—good and evil, as believable and engrossing when he sings about maiming unwitting victims and kissing Jesus as when he sings about being deeply in love.

“As everyone knows, there are only 25 letters in the alphabet,” Merritt drolly set himself up for a modest, one song encore of “Zombie Boy.” But hey, if, as he told us sheepishly, you only have two “Z” tracks to choose between at the end of the day, you’re doing something different than most, to be sure, but you’re definitely doing something right.

– Emily Gawlak