PENNY GOODWIN – PORTRAIT OF A GEMINI.

dereksmusicblog ♦ November 11, 2026 ♦ Leave a comment

Penny Goodwin – Portrait Of A Gemini.

Label: P-Vine.

Format: Vinyl. 

Originally recorded between 1973 and 1974 for the boutique Milwaukee-based imprint Sidney Records, Penny Goodwin’s ‘Portrait Of A Gemini’ occupies a revered status as one of the most extraordinary and elusive masterpieces of mid-seventies private-press soul-jazz. 

A native of Milwaukee who honed her distinctive vocal phrasing and improvisational instincts while performing alongside childhood friend and fellow jazz luminary Al Jarreau, Goodwin possessed a rich, highly versatile contralto voice. Her remarkable instrument allowed her to navigate disparate musical landscapes with effortless grace, pivoting seamlessly from smoky, introspective late-night balladry to driving, hard-hitting funk arrangements.

This stood Goodwin in good stead when she recorded ‘Portrait Of A Gemini.’ Under the meticulous musical direction of pianist and arranger Ray Tabs, and propelled by an elite ensemble of studio heavyweights – including legendary guitarist Phil Upchurch, powerhouse drummer Morris Jennings, and virtuosic saxophonist Don Myrick, alongside lush, sweeping string arrangements performed by members of the Chicago Symphony Orchestra – ‘Portrait Of A Gemini’ successfully bridges the gap between accessible commercial soul and sophisticated jazz intellect.

Long coveted by international vinyl collectors and hip-hop producers searching for pristine, soulful breaks, the record stands as a masterclass in dynamic light and shade, balancing intricate harmonic textures with profound emotional resonance.

Side A. 

The album launches with ‘Today Is The First Day,’ an uplifting, breezy soul-jazz declaration that immediately sets a sophisticated yet welcoming tone. Expertly arranged by Ray Tabs, the opening composition pairs a tight, driving rhythm section with the floating, ethereal flute lines of Myrick and sparkling textures of electric piano. Goodwin’s voice enters with absolute clarity, confidence, and poise, establishing the dual nature of the record: a seamless synthesis of sophisticated musical ambition and deeply accessible, soulful warmth. 

Penned by the legendary songwriting partnership of Ralph MacDonald and William Salter, ‘Trade Winds’ serves as a mid-tempo masterclass that highlights Goodwin’s exceptional gifts for emotive storytelling and lyrical interpretation. Anchored by the subtle, atmospheric conga work of Alan Love and James Johnson’s resonant, grounding walking bassline, Goodwin delivers a haunting, melancholic performance that lingers long after the notes fade. Through carefully measured phrasing and nuanced dynamic shifts, she captures the profound poetic weight of the composition, imbuing every line with a palpable sense of longing and depth.

‘Rain Sometimes’ is a lush, sweeping ballad composed by Arthur Hamilton. Here, the arrangement blooms with cinematic beauty as members of the Chicago Symphony Orchestra weave rich string textures behind Goodwin’s velvety vocal phrasing. Her delivery is intimate and unhurried, demonstrating remarkable vocal control on the long, held notes. 

Goodwin takes on Gil Scott-Heron’s iconic tribute ‘Lady Day and John Coltrane’ with thrilling intensity. Driven by a driving rhythm section and funk-infused keys, her performance matches Scott-Heron’s rhythmic urgency while injecting a distinctly soulful vocal warmth. It stands as one of the definitive vocal covers of the track. 

Closing Side A is a  low-slung, head-nodding groove that highlights the rhythm section’s impeccable pocket on ‘That’s All Right With Me.’ Goodwin’s phrasing turns casual and bluesy, floating over Tabs’ electric piano vamps and subtle percussion accents with an effortless, swaggering confidence. 

Side B.

A brisk, two-and-a-half-minute slice of upbeat jazz-pop, ‘He’s Come Back’ is the perfect way to open Side B. Featuring the crisp, articulate guitar lines of Upchurch alongside snappy, punctual horn accents, the track moves with infectious momentum. Rather than limiting its scope, the song’s concise brevity only heightens its punchy, joyful energy, leaving a lasting impression through its tight execution and exuberant feel and is vibrant and satisfying. 

Goodwin and Tabs original ‘Too Soon You’re Old’ is full of profound introspection. It is, without doubt, one of the album’s undisputed highlights. Opening with delicate instrumentation and building into a dramatic, soul-stirring crescendo, Goodwin tackles the passage of time with emotional depth that gives the track a haunting, lingering weight. 

Slow Hot Wind” is a sultry, simmering rendition of the Henry Mancini classic that showcases Goodwin’s astonishing vocal command. Under Tabs’ direction, the arrangement moves at a mesmerising crawl, dripping with late-night atmosphere and cinematic tension. Goodwin utilises her lush lower register to brilliant effect, letting her vocal phrases hang lazily in the expansive spatial margins created by the minimalist percussion and soft, atmospheric flute fills. It is a masterclass in restraint and mood-building, transforming a standard into a deeply visceral, hypnotic piece of late-night soul-jazz. 

Goodwin reinterprets Marvin Gaye’s legendary anthem ‘What’s Going On’ not as a direct imitation, but as a deeply personal, gospel-tinted soul-jazz meditation. The tempo is measured, allowing room for her vocal ornamentations to shine while maintaining the original’s poignant social urgency. 

The album concludes on a profound, deeply personal note with a breathtaking, soul-stirring cover of ‘Amazing Grace.’ Performed intimately alongside her brother, flutist Cleo Goodwin Jr., as a moving tribute in memory of their late father, this sparse, six-minute gospel arrangement completely strips away the grand-scale production of the earlier tracks. Instead, it exposes pure, unadorned vocal power and raw spiritual resonance. With Goodwin’s commanding voice intertwined with the plaintive, expressive tones of her brother’s flute, the performance serves as a transcendent closing statement – providing a hauntingly beautiful and emotionally resonant resolution to the entire musical journey. 

‘Portrait Of A Gemini’ ultimately transcends the modest boundaries of its private press origins to stand as one of the most complete, auteur-driven vocal jazz albums of the 1970s. Released on Sidney Records – a tiny independent imprint based out of Milwaukee – the record operated without the formidable promotional machinery of Blue Note or the expansive global distribution power of Atlantic Records. Yet, what it lacked in corporate backing and commercial reach, it more than compensated for through sheer artistic excellence, immaculate session craftsmanship, and Penny Goodwin’s undeniable, generation-defining vocal talent.

The fundamental brilliance of the record lies in its duality—a quality remarkably fitting for an album bearing the sign of the Twins. Goodwin effortlessly navigates contrasting sonic worlds: balancing the gritty, head-nodding funk of legendary Chicago session veterans Phil Upchurch and Morris Jennings with the elevated, classical sophistication of string arrangements performed by members of the Chicago Symphony Orchestra. Across the album’s track-list, she moves seamlessly between the fiery, rhythmically explosive tribute of ‘Lady Day and John Coltrane’ and the heartbreaking, introspective vulnerability of ‘Too Soon You’re Old,’ maintaining her signature tonal warmth, breath control, and structural precision throughout every performance.

Decades after its initial 1974 pressings quietly slipped into local obscurity, this reissue by visionary label P-Vine has finally given the album its long-overdue critical reappraisal. ‘Portrait Of A Gemini’ is far more than an elusive holy grail for vinyl collectors or a rich quarry of pristine breaks for crate-digging hip-hop producers. It remains a timeless, immaculately preserved monument to an unsung queen of American soul-jazz, capturing a powerhouse vocalist operating at the absolute peak of her expressive and technical powers.

Penny Goodwin – Portrait Of A Gemini.