(ThyBlackMan.com) There’s something about Bobby Womack’s voice that hits you in the soul before you even realize what he’s saying. Maybe it’s the grit, maybe it’s the honesty—but whatever it is, it sticks with you. I grew up hearing his songs in the background—at family cookouts, during quiet car rides, and sometimes when someone in the house had their heart broken and needed a little music therapy. It wasn’t until I got older that I really started to listen to Bobby Womack, and once I did, I understood why his music continues to resonate decades later.
Womack was more than just a soul singer. He was a storyteller, a truth-teller, and sometimes, an emotional mess laid bare in the most beautiful way. His catalog spans confessions of love, cries for redemption, and groove-heavy declarations of who he was. Every track is like opening a diary page—raw, detailed, and full of humanity.
In a time when music often feels overly polished or manufactured, diving into Womack’s work is like rediscovering the beating heart of soul. These eight songs I’ve chosen aren’t just fan favorites—they’re emotional landmarks. Whether you’re revisiting them or hearing them for the first time, they each have something powerful to offer.
So let’s talk Bobby. Let’s revisit the gravel and gold in his voice. And maybe, like me, you’ll find pieces of your own story in his.
1. “Across 110th Street”
Arguably Bobby Womack’s most recognized work, “Across 110th Street” is more than just a soundtrack cut—it’s a socio-political commentary, a street sermon, and a cinematic soul masterpiece. Originally recorded for the gritty 1972 Blaxploitation film of the same name, the song quickly took on a life of its own. Womack’s raspy yet poignant delivery captures the harsh realities of life in Harlem, where the titular street marked a real and symbolic boundary of poverty and struggle. In the early ’70s, 110th Street was the line between aspiration and survival, and Womack poured every ounce of that tension into this track.
Musically, the track features lush strings, a steady bass groove, and urgent percussion, echoing the urgency of Womack’s lyrics: “Snorting that coke, shooting that dope, man you’re copping out/Take my advice, it’s either live or die/You’ve got to be strong if you want to survive” The string arrangements, reminiscent of Curtis Mayfield’s scoring style, wrap the song in drama while allowing Womack’s storytelling to soar. There’s a brilliant juxtaposition of beauty and brutality in the instrumentation—graceful violins meet streetwise rhythm, just like the dream of upward mobility meets the grit of the daily hustle.
What sets this track apart, even decades later, is its honesty. It doesn’t glorify street life or play into clichés. Instead, it acknowledges the desperation, survival, and small victories that make up inner-city reality. Womack isn’t detached—he’s lived this, and that lived-in truth gives the song its enduring power. It’s not just an anthem for a movie, but a voice for the voiceless in a time when Black stories were too often ignored.
In today’s world, where issues of racial inequality and economic disparity remain ever-present, “Across 110th Street” feels as relevant as ever. It is a reminder that the past often haunts the present, and Womack’s work becomes a bridge between generations. The track’s inclusion in films like Quentin Tarantino’s Jackie Brown introduced it to new audiences, ensuring its continued legacy. Listening to it now, you hear more than just music; you hear a man fighting to be heard above the noise of systemic oppression and urban decay. Womack didn’t just sing it—he lived it, and that makes all the difference.
2. “If You Think You’re Lonely Now”
A cornerstone of romantic soul, “If You Think You’re Lonely Now” is Bobby Womack at his most vulnerable and confrontational. This track perfectly captures the complexity of relationships—the way love can twist into resentment and how longing can quickly turn into loneliness. It’s a ballad, but one imbued with emotional grit and painful honesty. Released in the early ’80s when Womack was grappling with personal demons and artistic resurgence, this track stands out as one of his most emotionally transparent works.
Musically, it’s stripped down, with a focus on Womack’s expressive voice and a slow, bluesy guitar riff that underscores the melancholy in the lyrics. He sings with a preacher’s conviction and a lover’s hurt, turning every line into a plea, a warning, and an ultimatum all at once. “Wait until tonight, girl” is more than a lyric—it’s a chilling promise of solitude, and Womack delivers it with a mix of defiance and sorrow that cuts deep.
The brilliance of this track lies in its tension. Unlike typical heartbreak songs that beg for reconciliation, Womack leans into the separation, challenging the listener to consider their role in the breakdown. The song is accusatory but not cruel—it’s human, complex, and heartbreakingly honest. His voice cracks and soars in all the right places, capturing both righteous anger and aching love in one breath. It’s the kind of performance that feels too intimate, as if you’re overhearing a private conversation.
In the modern era, when relationships are often reduced to swipes and emojis, this song is a slow-burning reminder of what it means to truly feel abandoned. The song’s legacy also lives on in its influence—K-Ci Hailey’s powerful cover version helped introduce it to ’90s R&B fans, but Womack’s original remains the definitive take. “If You Think You’re Lonely Now” is a masterclass in soul music’s emotional power and a testament to Womack’s ability to turn personal pain into universal art.
3. “Harry Hippie”
Written as a tribute to his brother, the late Harry Womack, “Harry Hippie” is both whimsical and tragic. The track originally appeared on Understanding, an album that saw Bobby maturing in both theme and style. With a relaxed, almost tropical groove, “Harry Hippie” stands out in his catalog for its easygoing tone juxtaposed with underlying sorrow. It’s not a protest song in the traditional sense, but its message about nonconformity and choosing joy over societal pressure is a form of rebellion.
The song portrays Harry as a free spirit, someone uninterested in material gain or societal pressure. Womack sings about his brother’s carefree nature with affection and a bit of exasperation. Lines like “He’s got a woman he loves, but he doesn’t have the time to pick up his check” add character and humor to the narrative. Yet beneath the charm lies a deeper meditation on freedom, responsibility, and eventual loss. It’s both a celebration and a quiet warning.
Tragically, Harry was murdered in 1974, just two years after the song’s release, giving it a posthumous weight that reshapes how listeners interpret it. What was once a lighthearted ode now reads as a eulogy. It’s impossible to listen without feeling the ache of hindsight. The juxtaposition between the breezy melody and the real-life outcome is haunting. Bobby Womack’s voice, already infused with emotion, now carries an extra burden of grief and memory.
In today’s world, where mental health and self-expression are finally becoming common discussions, “Harry Hippie” feels like an anthem for those who choose to live on their own terms. It invites empathy for people who don’t fit into societal molds. The mellow vibe invites repeated listening, while its lyrical poignancy keeps you grounded in reality. “Harry Hippie” is as much a philosophy as it is a song—and a necessary reminder that not all who wander are lost.
4. “Woman’s Gotta Have It”
This track is Bobby Womack’s soulful guidebook on how to keep a relationship intact. “Woman’s Gotta Have It” merges Southern wisdom with Northern soul, offering practical advice in the form of a funky groove. Womack’s conversational tone makes it feel like he’s sitting next to you, sharing the secrets of love over a glass of whiskey. There’s a lived-in quality to his voice here, as if he’s not just singing from theory, but from experience—and maybe a few regrets.
The instrumentation is rich but not overpowering. Horns punctuate the melody, and the rhythm section lays down a steady, satisfying groove that feels like a slow, confident strut. The backing vocals add warmth and a communal vibe, reinforcing the song’s message like a chorus of uncles nodding in agreement. The groove is smooth, but there’s urgency in Womack’s delivery—this isn’t just advice, it’s a plea to do better before it’s too late.
Lyrically, it’s both a warning and a revelation. “A woman’s got to have it / To know that she’s been loved,” he sings with the kind of conviction that comes from hard-earned experience. The brilliance of the song lies in how it balances vulnerability and authority. Womack acknowledges emotional needs without condescension, offering a rare male perspective that’s empathetic and mature. He doesn’t just romanticize love—he respects it.
What makes the song so enduring is its universality. It speaks to men and women alike, encouraging emotional availability and active effort in romantic partnerships. In a time when gender roles and emotional labor are being reevaluated, the song remains insightful and strangely modern. Even today, “Woman’s Gotta Have It” can spark a conversation—or an argument—about relationship dynamics. That makes it not just a classic track, but a conversation piece. Womack, once again, delivers more than soul—he delivers soul food for thought.
5. “That’s the Way I Feel About ‘Cha”
With “That’s the Way I Feel About ‘Cha,” Womack perfected the art of the confessional love ballad. This was his first big solo hit after leaving The Valentinos and working as a session musician for icons like Sam Cooke and Aretha Franklin. The track marked a turning point in his career—it was the sound of a man stepping into his own as a solo artist, armed with nothing but his weathered voice and his truth. The vulnerability in this song doesn’t come across as weakness; instead, it’s a quiet kind of courage that only deepens the intimacy.
His voice carries a kind of world-weariness that speaks to someone who’s been through love’s ups and downs but still chooses to care. Womack’s phrasing is conversational, even tender—like he’s not just singing to someone, but with someone. The arrangements are subtle—background harmonies, gentle organ swells, and restrained percussion give Womack all the space he needs to expose his emotional core. You can almost hear him exhale between phrases, as if laying down the weight of a relationship that’s been both beautiful and bruising.
“I’m in so much love with you,” he croons, not as a boast but as a confession, exposing his heart without hesitation. It’s that specific blend of masculine vulnerability and emotional honesty that gives the song its staying power. Many love songs make declarations; this one makes admissions. That’s a harder path to walk artistically, and Womack walks it barefoot—scraping every ounce of feeling into the mic.
In today’s fast-paced music landscape, where emotional depth often takes a backseat to catchy hooks, this song is a reminder of how profound a simple love song can be when delivered with sincerity. It’s soul music at its most naked. It’s the kind of track that deserves late-night listening with the lights low, the kind of record that speaks louder with each spin. For lovers and the lonely alike, it’s timeless.
6. “I Wish He Didn’t Trust Me So Much”
By the mid-1980s, Bobby Womack had weathered more personal storms than most artists care to admit. Addiction, grief, betrayal, and creative reinvention were all chapters in his book by then—and that life experience poured into “I Wish He Didn’t Trust Me So Much.” On the surface, the song is about betrayal, but Womack turns it into a meditation on guilt, loyalty, and the emotional chaos that can occur when love and friendship intersect.
The track features slick ’80s production—synth lines, reverb-heavy drums, and layered background vocals—yet Womack’s gritty delivery cuts through the polish. His voice is no longer the smoother croon of his early years; by 1985, it had become a cracked mirror reflecting regret and desire. Every word feels weighted. You can hear the torment in his delivery, a man almost pleading for someone—anyone—to take this moral burden off his shoulders.
This is one of the rare songs that explores betrayal not from the perspective of anger, but from internal conflict. “I wish he didn’t trust me so much” isn’t a sneer—it’s a sigh. The protagonist doesn’t want to fall for his friend’s woman, but he can’t deny the pull. That complexity makes it a unique entry in Womack’s catalog. It’s not about the heat of lust or the drama of confrontation; it’s about the slow erosion of boundaries and the quiet devastation that follows.
Listening to it now, the song fits within conversations about emotional fidelity, masculine vulnerability, and the gray areas of human relationships. In a world where loyalty is expected but rarely examined, Womack holds up a mirror to the difficult spaces in between. It’s a thought-provoking track that still resonates, especially for listeners who appreciate emotional nuance in songwriting. Few artists could make moral ambiguity sound this poetic.
7. “Facts of Life”
“Facts of Life” is one of Bobby Womack’s most overlooked masterpieces—tucked away on the Facts of Life album, which is itself a treasure trove of soulful introspection. While not a chart-topper, the title track is Womack at his most philosophical. It’s a quiet storm of acceptance and maturity, a ballad not about heartbreak, but about the wisdom that follows it.
From the very first line—“He’ll never love you the way that I love you”—you know this isn’t your average soul song. Womack sings like a man who has lived through the emotional battlefield and come out not bitter, but reflective. The lyrics are less about getting the girl and more about understanding her choices, even when they hurt. It’s rare to hear a man express this level of emotional restraint and clarity in a love song, especially during the hyper-macho 1970s.
The arrangement is minimal, allowing every syllable to linger. A soft electric piano floats over delicate strings, while Womack’s voice—smoky, seasoned, and aching—guides the listener through a confession wrapped in wisdom. His delivery isn’t pleading. It’s peaceful. He’s not trying to change the outcome—he’s just telling the truth, and that truth is what gives the song its quiet power.
In 2025, when emotional intelligence is finally becoming a more valued trait in music and life, “Facts of Life” feels like a precursor to modern vulnerability. It’s a track for anyone who’s loved and lost and come out of it with grace instead of rage. For listeners willing to go deeper into Womack’s catalog, this song is a revelation—gentle, thoughtful, and unforgettable.
8. “I’m a Midnight Mover”
Co-written with Wilson Pickett, “I’m a Midnight Mover” is a funky, upbeat track that showcases Bobby Womack’s raw energy and swagger during his early solo years. It’s less about heartbreak or introspection and more about movement—literal and emotional. This song brims with momentum, as if Womack couldn’t sit still long enough to explain what he’s running toward—or from. It’s a prime example of how soul music in the late ’60s was starting to flirt with funk’s faster pulse and dancefloor appeal.
The song’s driving beat, energetic horn section, and slick guitar licks make it a party anthem, but Womack’s vocal delivery keeps it grounded in emotional depth. He doesn’t just glide over the beat—he rides it with purpose. There’s joy in his tone, but there’s also something manic, almost desperate. That duality makes the track stick. It’s the soundtrack to a man on the move—not just physically, but emotionally.
Lyrically, the song plays with the idea of the restless lover, the man who can’t stay still or settle down. It’s playful but tinged with sadness, like a man who knows he’s running from something he can’t quite name. “I’m a midnight mover,” he repeats, and you get the sense he’s trying to convince himself as much as anyone else. Is it about chasing love—or escaping it before it turns to hurt? That tension gives the song emotional resonance beneath its groove.
Today, “I’m a Midnight Mover” still works on retro soul playlists or dancefloor throwback sets. It captures a side of Womack that was bold, alive, and unfiltered. In an era where artists often box themselves into emotional or musical lanes, this track reminds us that soul can be both thoughtful and thrilling. As a closer to this journey through Womack’s discography, it feels just right—energetic, layered, and impossible to ignore.
Going back through Bobby Womack’s discography feels like sitting down with an old friend—one who’s brutally honest, often flawed, but always full of wisdom. Each of these eight songs reflects a different facet of who he was as an artist and as a man. There’s the street poet in “Across 110th Street,” the wounded lover in “If You Think You’re Lonely Now,” the wise romantic in “Woman’s Gotta Have It,” and the spiritual survivor in “No Matter How High I Get.” Together, they show just how much Womack poured into his music—heart, hurt, soul, and swagger.
These songs don’t just belong in a museum of classics. They belong in your daily playlist, your nighttime reflections, your long drives, and quiet mornings. They speak across generations, cutting through trends and reminding us of what real storytelling sounds like. In a way, listening to Womack now feels like an act of preservation—not just of a voice, but of truth in music.
If you’ve never gone deep with Bobby Womack, this is your invitation. And if you’re already a fan, then you know: no one quite lays it bare like Bobby. Long after the last note fades, he still has a way of staying with you.
Staff Writer; Jamar Jackson
