Hip-Hop & Soul N°100 – Vintage 2000s Music Videos

1 . Donell Jones – U Know What’s Up (w/ Lisa ‘Left Eye’ Lopes)

Released in 1999, Donell Jones’ “U Know What’s Up” is a quintessential late-’90s R&B anthem, effortlessly blending smooth vocal atmospherics with a bouncy groove that practically demands a head nod.

The track sits proudly on *Where I Wanna Be*, an album that Jermaine Dupri once called one of the best R&B projects ever—perhaps hyperbolic, but not wholly off base given the record’s staying power.

Produced by Eddie F. and Darren Lighty under Untouchables Entertainment, this is production that doesn’t try to outshine its lead but instead finds harmony in simplicity—clean percussion, an irresistible bassline, and a chorus built for radio replay.

The song nabbed a No. 1 spot on the Billboard Hot R&B/Hip-Hop list for eight weeks, and its No. 7 peak on the Hot 100 affirmed its universal appeal beyond genre loyalists.

Lisa “Left Eye” Lopes, in her guest feature, provides a sharper, playful counterpoint to the track’s laid-back suave, delivering a verse that’s both complimentary and instantly memorable.

The music video adds a layer of cultural cachet, featuring contemporaries like Usher, T.I., and Big Boi, while spotlighting Left Eye’s undeniable charisma.

This is R&B at its transitional peak—still tethered to the genre’s soulful past, but glimpsing the slick, pop-adjacent future on the horizon, making it a time capsule worth revisiting.

Featured on the 1999 album “Where I Wanna Be”.

Lyrics >> Review >> More by the same : Official Site

2 . Mos Def – Ms. Fat Booty

Released in 1999, “Ms. Fat Booty” serves as hip-hop’s witty ode to fleeting attraction and ephemeral connections, housed in Mos Def’s seminal album “Black on Both Sides.”

Ayatollah, the producer, weaves Aretha Franklin’s “One Step Ahead” into the track with deft precision, balancing smoky nostalgia with raw grit while sampling unreleased vocals from Franklin’s archives.

The beats are steady and rich, avoiding overproduction, giving Mos Def ample room to showcase his vivid lyrical storytelling.

The song doesn’t rely on bombast but on humor and finely spun cultural references, simultaneously reflective of late ’90s hip-hop’s lyrical complexity.

The track brushes shoulders with mainstream recognition, peaking modestly on charts, but carves its niche in the hearts of hip-hop purists, reflecting Mos Def’s penchant for layering levity with introspection.

Underpinned by RAWKUS Records’ independent grit, the song echoes Mos Def’s consistent critique of unacknowledged Black contributions to modern music genres.

While cementing Ayatollah’s production talent, the song distances itself from commercial spectacle, situated instead as a quiet triumph within an evolving genre.

Featured on the 1999 album “Black on Both Sides”.

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3 . Will Smith – Will 2K (w/ K-Ci)

Released in 1999 as part of Will Smith’s *Willennium* album, “Will 2K” manages to capture the hyper-enthusiasm of a world bracing for Y2K—remember that overblown apocalypse?

Propelled by the production of Trackmasters, this funk-infused Hip-Hop track struts out with a confident swagger, bolstered by nostalgic nods to earlier musical eras.

The song leans heavily on nostalgia, sampling The Clash’s “Rock the Casbah” and Grandmaster Flash’s “Superslap,” creating a sonic time capsule that feels oddly timeless yet hilariously specific to its launch window.

K-Ci’s soulful croon adds texture to Smith’s bouncy, PG-friendly verses, while the infectious beat serves as the song’s shiny, unrelenting engine.

The video, which debuted in September 1999, ties into a sci-fi-laced time machine schtick, roping in cameos from familiar names like DJ Jazzy Jeff and Eve—because it wouldn’t be a millennial celebration without a quirky narrative and celebrity sightings, right?

Culturally, the track attempts to position itself as the ultimate millennium anthem but lands somewhere between a toe-tapping guilty pleasure and a commercialized time capsule.

Ironic perhaps, that a song designed to usher in the 2000s feels most relevant as a relic of 1999—proof that yearning for the future can sometimes leave you stuck in the past.

Featured on the 1999 album “Willennium”.

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4 . Diana Ross – Not over You Yet

By the late ’90s, Diana Ross was well past her peak chart dominance, but “Not Over You Yet” emerges as a shimmering attempt to adapt her legacy to the era of polished electronic pop.

This 1999 single, penned by Malik Pendleton and Kenneth Kelly and polished by Brian Rawling and Mark Taylor, doesn’t skimp on ambition—melding house beats, garage textures, and a disco backbone with Ross’s signature vocal flourishes.

The Metrophonic remix injects a sharper club sensibility, driven by a pizzicato guitar riff that’s as crisp as it is insistent, while the song’s drum buildup strives to command attention on the dancefloor.

Lyrically, it plays it straight and safe, spotlighting the emotional residue of heartbreak, a well-trodden theme that Ross handles with practiced elegance.

The music video, with choreographed sequences that hint at MTV’s golden age, attempts to echo the visual zeitgeist, but doesn’t quite transcend its late-’90s aesthetic roots.

While celebrated in some circles as mature and heartfelt, detractors dismiss it as overly mechanical—a clinical blend of genre influences without the emotional rawness her earlier works breathed effortlessly.

Commercially speaking, the song fared modestly across Europe, peaking respectably in the UK and Hungary but barely making a splash in Germany and the Netherlands, leaving its legacy firmly localized rather than universal.

Featured on the 1999 album “Every Day Is a New Day”.

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5 . Glamma Kid – Why

Glamma Kid’s **“Why”** is a late ‘90s concoction of dancehall swagger meeting electronic zest, a track that struts confidently into the genre-blurring arena of reggae-inflected club music.

Released on November 15, 1999, this single positions itself as one of the standout moments from Kid’s debut album, *Kidology*, a record that balances both the yearning for chart visibility and a tether to Caribbean roots.

Peaking at number 10 in the UK Singles Chart, it carves out its home in a moment when British pop audiences were increasingly attuned to dancehall influences, even if the track’s resonance failed to extend to France, the Netherlands, or New Zealand.

What sets “Why” apart is its rhythmic sensibility, stitching together bass-heavy beats and an eager, almost restless energy that leans into the genre’s electronic undercurrents without losing its Jamaican essence.

Kid’s voice oscillates between swaggering confidence and vulnerability, although, without an accompanying music video—or at least the absence of known details—there’s a visual gap that leaves the imagination to fill in the song’s cinematic potential.

One of two UK top 10 hits in 1999 (the other being “Taboo”), “Why” reflects a moment of promise for an artist flirting with mainstream attention while tethered to niche genres often relegated to the fringes of pop conversations.

The song skips meaningful lyrical exposition in favor of mood and groove, leaning heavily on its commitment to movement rather than introspection.

While the lack of broader international appeal underscores its geographically specific success, the track remains a timestamp of an era when British acts dipped their toes into dense, sun-soaked beats and electronic pulses with mixed results.

“Why” is neither a groundbreaking anthem nor a filler; it’s the sound of calculated experimentation operating somewhere between commercial ambition and genuine genre fusion.

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6 . Macy Gray – I Try

Released in 1999 as part of Macy Gray’s debut album *On How Life Is,* “I Try” is a track that balances precariously between vulnerability and defiance, showcasing Gray’s raspy, emotive vocal style.

Blending elements of jazz, blues, and R&B, the song communicates the ache of unrequited love with lyrics that oscillate between self-assured declarations and exposed fragility.

The instrumentation leans on a steady rhythm and smooth melodic lines, creating a sound that’s both approachable and layered enough to hold attention.

Unlike many of its late-’90s peers, it’s not an exercise in overproduction—its charm lies in its restraint and intimacy, qualities that were arguably out of step with the era’s pop trends.

Its cultural footprint extends to film soundtracks of the time, with appearances in movies like *Love Jones* and *Picture Perfect,* suggesting it was as much a mood as it was a hit.

“I Try” also carries historical weight, earning Gray a Grammy for Best Female Pop Vocal Performance and cementing her as a left-of-center figure in contemporary music.

Her unapologetic authenticity challenges traditional notions of pop stardom, offering something raw and refreshingly unpolished amid a more polished scene.

It’s this mixture of accessibility and emotional depth that continues to keep it relevant, even in an industry prone to forgetfulness.

Featured on the 1999 album “On How Life Is “.

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7 . Neneh Cherry – Buddy X ’99 (w/ The Dreem Teem)

“Buddy X ’99” is a fascinating artifact of late-90s remix culture, a time when UK garage was taking root while still carrying an underground edge.

The track, originally from Neneh Cherry’s 1992 album *Homebrew*, gets a full rework by The Dreem Teem, infusing it with infectious energy and distinctly British flair.

While the 1992 original bridged pop, hip-hop, and techno, this remix places the song squarely on the dance floor, trading its genre fluidity for the punchy swing of garage.

The production crackles with skipping snares, looped vocal fragments, and a nimble bassline that feels impossibly precise yet effortlessly cool.

Interestingly, a remix featuring The Notorious B.I.G. surfaced, though aligning his booming cadence with Cherry’s breezy defiance felt like a creative tension rather than a smooth collaboration.

Despite these modifications, Cherry’s sly message to a no-good “Buddy” remains intact, her voice both alluring and sardonic amid the sonic melee.

The remix may lack the complexity of the original but compensates by capturing the zeitgeist of its era—a transitional moment between niche club cultures and the mainstream co-opting of electronic music staples.

The odd blend of its provenance—a Swedish-British artist, a remix crew steeped in UK garage, and Biggie’s cameo—feels emblematic of pop music’s then-expanding global dialogue.

Does it reinvent the wheel? Hardly.

But “Buddy X ’99” serves as a curious time capsule where producers, artists, and listeners were testing connections, sometimes seamlessly, sometimes awkwardly, but always audaciously.

Featured on the 1992 album “Homebrew”.

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8 . Nas – Nastradamus

“Nastradamus” arrives with an edge as sharp as Nas’ lyrical prowess, embodying East Coast grit and hardcore sensibilities.

This title track from his fourth album teeters between introspection and provocation, encapsulating the rapper’s transition from “Nasty Nas” to his more mythic, self-proclaimed persona.

L.E.S.’ production frames the track with a sample from “The Monorail Express” by The J.B.’s, a move that anchors the beat in a funk-laden lineage while maintaining its aggressive bite.

The chanted chorus, hypnotic and unapologetic, reinforces Nas’ evolution and swagger, though detractors may argue it slides too close to self-indulgence.

Lyrically, Nas takes aim at Roc-A-Fella artist Memphis Bleek, fanning long-simmering industry tensions that bleeds into his broader feud with Jay-Z—rap beef served with a side of subtlety and scorn.

The accompanying 3-D music video, which features flashy effects and some dated tech experimentation, lands with mixed results: audacious in concept yet awkward in execution.

Chart performance underscores its divisive nature, climbing as high as #4 on the US Hot Rap Songs chart but barely scraping #92 on the Billboard Hot 100.

Its contradictions—part braggadocio, part visionary, part misstep—mirror Nas’ overarching artistic journey during this period.

“Nastradamus” straddles the line between ambition and excess, paving uneven roads to later career highlights like “Stillmatic.”

Featured on the 1999 album “Nastradamus“.

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9 . Gabrielle – Sunshine

Gabrielle’s “Sunshine” sparkles as both a late-’90s pop moment and a heartfelt nod to the timeless allure of classic soul.

Emerging from her 1999 album *Rise*, the track pairs a buoyant R&B groove with a sense of gentle nostalgia borrowed from early-’80s British pop.

Thematically, it likens the irreplaceable warmth of a cherished companion to the vitality of sunshine—a metaphor so on-the-nose it teeters dangerously close to cliché but ultimately manages to charm.

Its production, helmed by Richie Fermie and Jonathan Shorten, merges polished strings with an unfussy beat, maintaining its accessibility while hinting at something theatrical beneath the surface.

A modest success in Europe, it notably peaked at No. 9 on the UK Singles Chart and landed at No. 2 on the UK Hip Hop/R&B Chart, though it largely glanced off international charts—Netherlands at No. 98 is hardly a triumph.

Critically, it’s bolstered by trivia for geeks: it snagged gold certification in the UK, with sales surpassing 400,000, and found its way onto NME’s list of “25 Essential UK Garage Anthems,” thanks in part to an orchestral Wookie remix.

Reinterpreted in 2019 with DJ Spoony for *Garage Classical*, the track acquires an additional layer of intrigue, nodding to the genre’s enduring formative influence on British music.

Gabrielle’s voice, smoky yet hopeful, adds depth, managing to straddle the line between pop commerce and emotive sincerity.

Still, it’s not without its quirks—the production is pristine to a fault, and the unadventurous chord progressions keep it safe, even predictable.

Yet, in its simplicity lies its strength: “Sunshine” doesn’t pretend to be groundbreaking; instead, it offers an elegantly understated hymn to joy and connection that, for a moment, feels universal.

Featured on the 1999 album “Rise”.

Lyrics >> Review >> More by the same : Official Site

10 . Missy Elliott – Hot Boyz

Missy Elliott’s “Hot Boyz” throws you straight into the late ’90s, a moment when hip-hop swagger fused effortlessly with club beats, and Timbaland’s minimalist production was reshaping the genre’s soundscape.

The track doesn’t waste a second flaunting its unabashed decadence—cash, cars, and couture—but there’s a knowing smirk under all the opulence, as though Missy herself is in on the absurdity of the performance.

The beat is unmistakably stripped down, marked by Timbaland’s signature stuttering snares and spacey keys, giving the song an almost hypnotic loop that feels tailor-made for both radio dominance and sweaty, late-night spins on the dance floor.

Add in an official video packed with cameos—Eve, Nas, Q-Tip, and Lil’ Mo—and you’re looking at a bold statement demonstrating that Missy wasn’t just blending genres; she was corralling icons to orbit her unmistakable gravitational pull.

While her lyrics revel in street-culture bravado, her delivery brings a sly humor and rhythmically dynamic flow, elevating what might otherwise feel like pure material excess into a cheeky, self-aware anthem.

What makes “Hot Boyz” fascinating is the juxtaposition: the song is mechanically cold in its production while being undeniably warm in its charisma—call it a flex that knows when to wink.

At its core, the song encapsulates Missy Elliott’s ability to straddle contradictions: avant-garde yet commercial, edgy yet universally appealing, humor-laden without losing a beat of its authority.

“Hot Boyz” isn’t merely a hit; it’s a snapshot of late-’90s hip-hop culture commandeered by an artist unafraid to rewrite the rules with each audacious release.

Featured on the 1999 album “Da Real World “.

Lyrics >> Review >> More by the same : Official Site

11 . Whitney Houston – I Learned from the Best

Whitney Houston’s “I Learned from the Best” is a polished breakup anthem wrapped in a late-’90s R&B ballad framework.

Released in 1999 as part of the *My Love Is Your Love* album era, this track sits comfortably in the glamorized heartbreak lane, with a backdrop of lush David Foster production and a Diane Warren-penned melody that rises and falls like waves crashing against an emotional shore.

The song’s thematic core revolves around the lessons learned from a failed relationship—brimming with the confidence of someone who has walked out of heartbreak not unscathed but certainly enlightened.

The music video, directed by Kevin Bray, leans heavily on theatrical regret, as Houston performs for an intimate crowd that includes the symbolically regretful ex-lover, all while draped in cinematic lighting and high-gloss visuals.

Vocally, Houston channels restrained elegance into powerhouse crescendos, proving she doesn’t need vocal gymnastics to wrench feeling out of every line.

Commercially, it made respectable dents on the charts, hitting number 27 on the US Billboard Hot 100 and finding love on the UK and European charts, peaking as high as third in Iceland.

It even briefly ruled the dance floor, courtesy of Hex Hector and Junior Vasquez remixes that gave the song a three-week reign on the US dance charts—an ironic twist for a ballad that couldn’t feel more antithetical to club euphoria.

But the emotional weight of its lyrics and Houston’s delivery saves it from feeling like mere factory-made heartbreak fodder, letting it slot into her discography as a sturdy, if understated, effort.

In hindsight, it serves as a snapshot of pre-millennium pop balladry: meticulously produced, aching, and sincere, though not without its glossy, packaged veneer.

Featured on the 1998 album “ My Love Is Your Love“.

Lyrics >> Review >> More by the same : Official Site

12 . TLC – Dear Lie

“Dear Lie” operates as an intimate confrontation with deception, a theme rendered both personal and universal through TLC’s delivery.

Emerging from their futuristic *FanMail* album in 1999, the track channels the angst of T-Boz’s poetry into a polished, Babyface-produced R&B arrangement that feels both smooth and restrained.

The instrumentation leans on a subdued palette: Greg Phillinganes’s Wurlitzer hums softly, Nathan East’s bass provides a steady anchor, and Paulinho Da Costa’s percussion adds minimal but effective texture.

T-Boz and Chilli’s vocals exude a calm defiance, contrasting deceptively with the underwhelming commercial performance on U.S. soil, where the song plateaued at #51 on Billboard’s Hot 100.

Visually, the Bille Woodruff-directed music video failed to excite even its creators, an indifferent release strategy relegating it primarily to non-American markets, where its reception fared better.

Despite the glossy production and thematic heft, it lives in the shadow of TLC’s stronger, more dynamic hits of the ’90s.

Featured on the 1999 album “FanMail “.

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