PhD in breakup songs. Meditative Moodscapes, Atmospheric Folk.

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Alternative tragic Americana, invocations for peace & judgment reshaping with bleeding heart stream of consciousness poems. Anna May is an eclectic artist whose songs bear a placelessness that lends to their timeless nature. The deep exploration of heartbreak and trauma has been an ongoing quest throughout Anna's work. Her lyrics have been heavily textured by a lonesome whimsicality that finds itself most at home in the vastness of the American West or in landscapes of stark frontiers. Anna's music honors the nomadic spirit with memory, meditation & fresh interpretations of folk music and jazz influence. She honors a hope to enhance connection, humility, healing, and joy among people in the process of parting with typical genre rules.

 

One of Anna's primary artistic goals is to play with genre & create a sense of fluidity and expansion within the genre of folk, integrating thought provoking elements of jazz and experimental, allowing music to be a connective force for change and for good, combining the traditional with the avant garde.

 

With a penchant for bright dreams and small towns, folk ballads and cosmic, experimental dreamscapes, Anna’s music sails and soars with a genre defying fluidity that is entirely unique, with a vocal quality that touches something so deep and visceral. Her music is sadness, joy, love, insecurity, hopelessness and assuredness, all at once, mirroring the complexity of our human experience. Experiencing Anna’s songs is like conquering difficult hurdles and coming out on the other side with revitalized sense of hope, peace and renewal. She expertly mingles hope and despair, while crafting innovative songs that harness folk music in a jazz format.

 

 Anna's lyrical sensibility is steeped in wisdom, and layered with evocative musicality and metaphysical embroidery while eschewing the mainstream & parting with platitudes. Anna explores both estrangement and connection while taking cues from artists like Bob Dylan, Radiohead, Billie Holiday, Shawn Colvin, Neil Young, Jim Morrison, the Mamas and the Papas, Joni Mitchell, Joan Baez, Mazzy Star, kd Lang, Tom Waits, and many more. Anna has been compared to artists like Jeff Buckley & Aimee Mann, and seeks to tilt outside of the folk genre to achieve a multi dimensional soundscape.

 

 Anna is a dancer, music teacher, organist & poet, as well as a seemingly perpetually touring artist who loves to be fed inspiration by new destinations, creating music with emphasis on personal connection to place, & allowing for metaphysical elements to filter in, with the entirety of her work produced by Steve Rizzo at Stable Sound Studios.

 

Anna's love for the organic nature of live performance cannot be matched, but she savors the quietude of her minimalist approach to recording. Her next full length album since 2022's Detach is currently in the works. Since September 2024, Anna has released five critically acclaimed singles, "The Show", "Elegy", "The Cliff", "Fireflies and Buffalo", and "Atom Bomb". Anna's first, anticipated single release of 2026 will be "Crying at Erewhon".

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She steps into the new year with genuine momentum with her upcoming single, a sarcastic breakup song that is clearly country pop departure from her previous work, that captures the emotional honesty and songwriting skill that have been turning heads across the genre. Performed by Anna May and written by Anna herself, Crying at Erewhon is her emotional response to a breakup text received at a popular wellness outlet in LA. It has an upbeat hit potential, and is hooky. Full of biting wit, Anna is sometimes said to have a PhD in breakup songs.

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Anna says of the song : “When I first wrote Crying at Erewhon, I wanted a recording that reflected the analog echo & golden brimmed recordings of LA icons like the Mamas and the Papas, the Carpenters, the Beach Boys, etc to really give the song the glistening glow that it deserved, but I decided that it would be too dated and I wanted the song to sound like something brand new. I think that it does in its current incarnation.”

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Anna has performed at the Art of Elan series at San Diego Central Library, wildflower music & arts festival, treefort music festival, boston arts festival, Sawdust Arts Festival, water lantern festival, Earlville Opera House, trout lake hall, abbey arts in seattle, Whistle Stop Bar in San Diego, Globe Hall in Denver, Sheridan Opera House in Telluride, Club Passim in Boston, Hotel Cafe in Los Angeles, Coach House Concert Hall, Salesforce Tower in San Francisco, Brick and Mortar Music Hall in San Francisco, Volcanic Theater Pub in Bend, Broadway Comedy Club in Manhattan, the Mint in Los Angeles, Trip in Santa Monica, Spiderhouse Ballroom in Austin, Camden Opera House in Maine, Rockwood Music Hall in New York City, Wall Street Theater in CT, Crying Wolf in Nashville, High Dive in Seattle, Tennessee Brew Works in Nashville, Davis Public Library, The Underdog in Nashville, The Cobra in Nashville, Franklin's Main Street Festival, Larimer Lounge in Denver, PNC Live Studio, Camden Public Library, Duxbury Free Library, Snow Library of Cape Cod, Burlington City Arts, the Arts Cafe Mystic, the Folk Project, Cape Cod National Seashore, The Whiskey Room, The Space Ballroom, Folktale Winery, Wadsworth Mansion, Al's Den in Portland, 333 lounge in Brooklyn, Alberta Street Pub in Portland, Florence Griswold Museum in Connecticut, Brooklyn Music Kitchen, Club Car Bar,  City Winery Boston, Harvard and Stone in Los Angeles, The Freight in Berkeley, Golden Gate Park Bandshell in San Francisco, Live in the Bay in San Francisco, and many more. Anna was a performer at the 2025 Wildflower! Arts and Music Festival in Richardson, Texas, at the 2025 Whole Earth Festival in Davis, California. She has also performed at We Found New Music Showcase at Hotel Ziggy in West Hollywood, Kilowatt in San Francisco with King Dream, at Stella Prince's female folk showcase at Hotel Cafe & Harvard and Stone in Los Angeles and most recently, at the House of Blues San Diego, opening for Ariel Pink. In 2026 Anna also opened for Jolie Holland with Ricky Berger at Folk Arts Rare Records in San Diego and was a showcasing artist at the Durango Songwriters Expo. In March 2026, she was presented by legendary Berkeley venue, The Freight for their Community Series, and recently made her television debut as a featured guest on Live in the Bay on KRON in San Francisco. In spring 2026, Anna opened for Maggie Koerner, performed at the 2026 Topanga Banjo and Fiddle Festival in California, showcased with Gravel Road Music Group at Key West Songwriter’s Festival, and was a featured performer at Carlsbad City Library, and Soft Spot Songwriters Showcase at Desert 5 Spot in Los Angeles. Later this summer, Anna will perform at Songs in the Canyon Music Festival in Costa Mesa, Davis Music Festival, Hermosa Beach Fine Arts Festival, and later in the year at Gasa Gasa in New Orleans and Cafe Wha? in NYC. 

 

Anna will be returning to the Coach House Concert Hall to open for legendary western swing band, Asleep at the Wheel. Her new single Crying at Erewhon will be released by Blackbird Record Label in the summer of 2026.