Meanwhile, Holcomb was writing poetry and setting Shakespeare’s "Tempest" to music. The song cycle "Angels At The Four Corners", presented in 1989 (and unreleased on record), was her first foray into singing: Holcomb, Syd Straw, Peter Blegvad, and Jearlyn Steele-Battle portray members of a family at the center of a metaphorical story that is also partly autobiographical.

Holcomb was born in the deep South, in Georgia, and spent a poor childhood working on plantations in North Carolina. Years later she began studying music at the University of Santa Cruz, California, where she met Horvitz. In the 1970s they moved to New York and became part of the eclectic “downtown scene” with a band called White Noise.

Similarly, Robin Holcomb (Elektra, 1990) features her husband on organ and synth, Doug Wieselman on clarinet and sax, Dave Hofstra on bass, Danny Frankel on percussion, and Bill Frisell on guitars—one of the most imposing backing ensembles in the genre’s history.
The key element, however, is not the arrangements, which are both sparse and delicate, but her vocal register. Holcomb’s voice is a cold, melancholic lament, reminiscent of Nico, often sliding into subdued, sobbing melismas halfway between Eastern vocalism and Meredith Monk’s experiments. Her compositions are always underpinned by clear, precise melodies that traverse the terrains of Leonard Cohen, Kurt Weill, and Joni Mitchell. Through this vocal art that is at once humble and aristocratic, and the surreal arrangements, the music sometimes has a ceremonial quality, at other times it feels like the soundtrack of a severely tested mind. Her piano style (a hybrid of Erik Satie and Cecil Taylor) is simultaneously gentle, hypnotic, and subtle, while the lyrics evoke a cryptic, mysterious stream of consciousness.
Many tracks on the album are essentially children’s rhymes, refined to the point of becoming conceptual abstractions. The catchiest chorus, endlessly spinning upon itself, slow and ineffable, wrapped in dreamlike reverbs of electronic keyboards and echoing ghostly cadences, is that of Nine Lives. Even the complex harmonic structure of So Straight And Slow develops so that ultimately only a catchy verse remains, repeated like a magic formula.
The piano repeats its elementary tune like a music box in The American Rhine, providing the foundation for an enchanting clarinet and a caravan-like desert cadence, lending the piece an Eastern flavor.
Even more elaborate and degenerate is the theme of Hand Me Down All Stories, reduced to a cyclical, celestial, hypnotic element that interrupts the funky rhythm.

These are all very sweet melodies, sung by a fluid, impassive voice, immersed in an unreal context, propelled by mellow rhythms, counterpointed by surreal events, emerging from a collective subconscious that is timeless, millennial, shared by all from the earliest childhood onward.
Holcomb’s “roots” emerge in songs worthy of the Band, such as Troy, complete with gospel organ à la Richard Manuel, in the martial folk ballad Yr Mother Called Them Farmhouses, and in a tribute to Monk, the nocturnal bebop of This Poem Is In Memory Of.
The album has few rivals in the annals of female singer-songwriter history.

Rockabye (Elektra, 1992), with another combo of players from the same “circle,” failed, however, to repeat the same miracle. Holcomb can't quite muster the atmosphere of mystery that underpinned all the stories of her first album. Both the singing and the piano are livelier and more aggressive, and the melodies are less immediate. The standout tracks are Help A Man, halfway between the Band’s soul-rock sketches and Meredith Monk’s primitivist vignettes; the title track, a country lullaby in waltz time; When Was The Last Time, the most electric and rhythmically driven song of her career; the vibrant and intense Primavera, with a dreamlike organ effect; and above all the sorrowful gospel-jazz of The Natural World, which closes the work on a note of quiet anguish. It is an album of more conventional songs, with soul, jazz, blues, and folk harmonies making them intelligent and interesting, and the perfect fusion between her voice and her lyrics certainly remains.

Through just two albums, Holcomb had already established a classic style and created a magical universe that reflects the real world but with the simplification of emotions typical of fairy tales.

Little Three (Nonesuch, 1996) is an album of mostly solo piano vignettes: Wherein Lies the Good, Processional, The Graveyard Song, Tiny Sisters, The Impulse, Little Three, The Window.

The Big Time (Nonesuch, 2002) features Bill Frisell on guitar, besides Wayne Horvitz on organ. The lyrical Like I Care (Kate and Anna McGarrigle on backup vocals) is the emotional centerpiece, but her sensitive persona and her arranger's skills are more effectively displayed in the dramatic, solemn Pretend, the emphatic, martial You Look So Much Better (worthy of Warren Zevon), and the eerie I Want To Tell The Story (a whisper lost in a forest of ghostly sounds), three of her greatest songs.
She can't resist the postmodernist temptation to revisit genres and styles, from the sprightly folk rigmarole A Lazy Farmer Boy (with Danny Barnes on banjo and Eyvind Kang on viola) to the six-minute blues Engine 143, from the Broadway-ish pop tune I Tried To Believe (with a brass section and marching-band rhythm) to the tapping rhythm'n'blues interludes of Tell The Good Friend On Your Left (with horn section), but fundamentally the musical scores are rarely relevant.
What is missing is a coherent concept and maybe some flight of imagination. Holcomb and her sextet (her piano, two guitars, organ, bass and drums) are impeccable in delivering states of mind via subtle counterpoint, but their performance often smells of "routine". Holcomb seems to have composed an album around her lyrics, but perhaps forgetting that, by definition, lyrics are not enough to justify a song. Her somewhat shrill voice does not help either.

Solos (Songlines, 2005) is a collaboration with Wayne Horvitz. The title is due to the fact that each piece is a solo piano composition, alternatively by one or the other.

John Brown's Body J (Tzadik, 2006) featured Eyvind Kang on viola, Dave Carter on trumpet and Melissa Coleman on cello. The core pieces were instrumentals. One featured a female string quartet. However, it also included some of Holcomb's new songs, notably Pretty Ozu.

The Point of It All (Jewl) (september 2009), featuring Horvitz, guitarist Ron Samworth, Bill Clark (trumpet, flugelhorn), Peggy Lee (cello) and Dylan van der Schyff (drums), is mostly instrumental and improvised.

One Way Or Another (two volumes, 2022 and 2024) are collections of solo piano lieder.

Reno (Songlines, 2025), a collaboration with celloist Peggy Lee, contains both songs and instrumentals.