The iconic music of Thelonious Monk has inspired generations of instrumentalists and vocalists. The composer's singular style offers challenges ideal for interpretation. Organist Gregory Lewis has long been a Monk acolyte and specialist who is always in search of a new way to frame Monk's work. On Organ Monk Sings, Lewis joins forces with vocalist, lyricist, producer, and artistic director Raina Welch (professionally known as Ms. Raina) for a dramatic and original program of Monk compositions. Gregory Lewis is recognized as a Monk scholar and is best known for presenting Monk's repertoire on the Hammond organ. Seeking new ways to highlight Monk's music, Lewis began exploring the integration of voice into his long-running Organ Monk project. A longtime fan of vocalists who had tackled Monk's music, including Carmen McRae and Abbey Lincoln, he sought a collaborator who could bring something distinctive and fresh to the tradition. Lewis and Welch connected through New York's vibrant music circuit, and their musical chemistry developed naturally through performance, conversation, and a shared commitment to the Black American musical lineage. A classically trained vocalist, Ms. Raina studied at Long Island University Brooklyn and Temple University, refining her technique under the mentorship of soprano Alba Quezada Bloomgarden and mezzo-soprano Dr. Lorie Gratis, with advanced mentorship from soprano Christine Moore Vassallo and Grammy-nominated vocalist Carla Cook. In her crossover journey, Cook's influence grounded Ms. Raina's phrasing, rhythmic placement, and storytelling in the lineage of vocal innovators such as Carmen McRae, Abbey Lincoln, Leon Thomas, and Eddie Jefferson, preparing her for the interpretive and technical demands of Monk's work. Over time, Ms. Raina's engagement with Monk's repertoire deepened through Lewis's perspective as an organist and her own study of the Monk vocal tradition shaped by McRae, Lincoln, Thomas, and Jon Hendricks. The two artists discovered a shared creative vision to reimagine Monk's body of work through the voice, not as novelty but as narrative. Ms. Raina led the project's artistic direction, curating repertoire, shaping the dramatic arc, and co-producing the sessions alongside Lewis. Drawing from her classical discipline, she conceived Organ Monk Sings as a sonic play, a narrative suite exploring love, loss, and revelation through Monk's compositions. Her original lyrics for "Let's Cool One" extend Monk's vocal lineage through a modern lens, merging his compositional wit with personal narrative and emotional depth. The project unfolds in four acts, mirroring the structure of a stage work with overture, scenes, interludes, and grand finale. The track sequence itself tells a story that moves from romantic infatuation to heartbreak, introspection, and renewal. A performance at Arthur's Tavern in New York's Greenwich Village at the end of 2024 proved pivotal, featuring saxophonist Jerry Weldon and drummer Nasheet Waits. Their sensitivity and attention to detail made for an ideal performance, making them the natural choice for the recording sessions held in June 2025 at Tedesco Studios in Paramus, New Jersey. Organ Monk Sings features Gregory Lewis on Hammond B2, Jerry Weldon on tenor saxophone, Nasheet Waits on drums, and Ms. Raina on vocals. The program spans eighteen Monk compositions and runs approximately sixty-two minutes, moving fluidly between solo organ, duos, trios, and full quartet settings. Ms. Raina selected the repertoire, including several pieces Lewis had never previously recorded. She crafted a cohesive dramatic sequence, incorporating instrumental tracks as overtures and interludes. Heard as a whole, the program unfolds like a tragic love story, beginning with infatuation, moving through turmoil, and ending in quiet reflection.