On G. Dep’s “Special Delivery,” after an opening, eight-second bombardment of “Yo, yo, yo!” running from his mouth—followed by the announcement of his ever-evolving moniker, “P. mothafucking Diddy”—the founding CEO of Bad Boy Records chanted, “We still here! Ain’t going nowhere!” During the minute-long time frame of his rant, he’d declare, “the saga continues,” both as a plug for Bad Boy’s all-star rostered compilation album released that summer 2001, and as an indication that the label was here to stay, despite what most predestined.

In the original music video, Diddy does his signature bop as the “Chairman of Bad Boy Express” (a spoof of the package courier service, FedEx)—an adrenaline-ringing 808 from the clubbanger’s instrumental fueling his dance moves, G. Dep’s “rap vampire” punchlines, a woman coquettishly inquiring “can I have that?,” and the birth of the original Harlem Shake. Diddy’s arrogant talk on the Harlem anthem—meant for the streets worldwide—signaled Bad Boy’s looming presence, bound to redesign the aesthetics and conversations surrounding the new millennium.

A year prior to the release of the tone-setting “Special Delivery,” the Gregorian calendar simultaneously reached a new century, decade, and golden age of transforming technology and progressive points of view. This important time shift seemed to be the bookend for Bad Boy Records to most critics. With the death of the empire’s grandmaster talent The Notorious B.I.G. three years prior—and the aftermath being an onslaught of “he’s turning hip-hop into a commercial pop joke” condemnations directed towards Diddy upon him winning Grammys and earning two No. 1 and deuce No. 2 hits for 1997’s No Way Out—Bad Boy needed some remodeling to be taken seriously again. It sort of meant goodbye to the gold-tinted, flashy visuals directed by Hype Williams, along with the hip-hop soul stylings of Puff Daddy, and hello to embracing an assortment of future talents who’d fit the icy and sleek branding of Diddy.

Coincidentally, January 3, 2000 marked the release of Bad Boy Records’ first commercial single of the aughts: “Notorious B.I.G.,” a song posthumously fronted by the rapper himself, featuring Lil’ Kim and Puffy, over a nostalgic-funk Duran Duran sample. Undeniably, the move gestured the end of an old era, but the start of the legacy it left behind. A Buffalo native going by the stage name of Black Rob got his start that March with his debut, Life Story. With a menacing violin and Timberland boot-stomp that reworked some Ruff Ryder sonics, “Whoa!” became the album’s hit single, reinvigorating the sound of New York street hip-hop, and ultimately guiding the choral-call-and-beat-response that drove Bad Boy hits.

That September, it became clear that Diddy wasn’t planning on dropping his label’s affinity for promoting within the music, as Shyne dropped his debut single, “Bad Boyz.” The then-20-year-old Belizean rapper had a slower draw that strikingly matched The Notorious’, but with a working class West Indies/Central American patois built from his childhood immigration to East Flatbush, Brooklyn. Shyne’s impending reign on the hip-hop scene, and a possibility of inheriting the throne B.I.G. left behind, would be cut short due to a ten-year prison sentence for a Manhattan club shooting incident.

As Bad Boy tried to rework its hip-hop division—including the release of 2001’s The Saga Continues… and its grungy-country guitar riddler “Bad Boy For Life”— the label played a part in redirecting contemporary R&B. The standout from The Saga Continues… had been “Can’t Believe,” a slinky midtempo duet between Carl Thomas and the label’s First Lady, Faith Evans. Evoking the sentiments of Spanish Harlem heartbreak, the song sampled “Phone Tap” from Nas’ supergroup, The Firm. According to the lyrics, it had been hard for both singers to fathom the sudden end to a relationship. What stuck out the most was the choral mention of “I’m emotional,” a suggested nod to Carl Thomas’ debut album, Emotional.

Hailing from Aurora, Illinois, and repping Bad Boy, Carl Thomas helped define the long-gazing, male R&B sound of the aughts. Instead of offering a neo-soul spin like Musiq Soulchild or an urban, dance-pop tilt such as Usher, Thomas led the scene with quiet storm vibes reminiscent of a new age Luther Vandross or Teddy Pendergrass.

His first single, “Summer Rain,” had been breezy enough for limited play on radio, but the follow-up, “I Wish,” proved to be the singer’s breaking moment. Belting regretfully in his silky baritone octave, Thomas provided male listeners (most importantly, the good guys) an iconic refrain: “I wish I never met her at all / Even though I love her so / She got love for me / But she still belongs to someone else.” Although “I Wish” became the album’s highest peaking song—at No. 20 on the Billboard Hot 100—the titular track would be helmed as the album’s core. “Emotional” sampled the somber instrumental of Sting’s 1993 ballad “Shape of My Heart,” but emphasized raininess as a way to perfect the quiet storm genre to a tee. Diving further into that format’s sensuality, Thomas tapped into Tyrese’s tier of babymaking R&B with deep cut-turned-late nite radio staple, “Lady Lay.”

With his raw delivery and sentimental crooning, Carl Thomas had joined the likes of Brian McKnight, manifesting wedding-centric R&B (see: Thomas’ “Special Lady”). While most of his music was meant for walking down the aisle, 112’s had been for the wedding reception dancefloor. The Atlanta quartet of Q, Daron, Slim, and Mike received a huge following as one of the more underrated boy bands of the 90s, after the release of their ’96 self-titled debut album and the ’98 follow-up, Room 112.

Although they gained signature Top 20 hits on the all-encompassing Hot 100, from both albums, such as “Only You,” “Cupid,” and “Anywhere” (as well as a featured charttopper on “I’ll Be Missing You”), the group was unfamiliar with the Top 10 as a lead. That would change with their third Bad Boy studio album, 2001’s Part III. The first single, “It’s Over Now,” relied on a sample of Mobb Deep’s infectious “Quiet Storm”—it’d become their first to top the R&B and hip-hop charts, peaking at No. 6 on the Hot 100. They’d earn their highest charter with “Peaches And Cream,” a song that embodied overarching 2000s-ness. Ultimately, the electro-bounce of that song would be sweetened and complemented by “Dance With Me.”

Representing for the ladies of R&B, Faith Evans was also on her third album by 2001. The songs on the project played as extenuations of the what she explored on her first two LPs. “I Love You” placed an electro-hop&B spin on the quiet storm she perfected with 1995’s “Soon As I Get Home,” as “Burnin’ Up” recalled the post-disco flare that existed on 1998’s “Love Like This” and “All Night.” Evans managed to tackle some hip-hop as well, rapping, “I said I know it’s not too ghetto / You betta check yourself, respect yourself / You betta go for self because I flow for self” on the defiant “You Gets No Love.”

Musically, Bad Boy Records had been proving to hold itself down, even allowing room for the No.2-hit wonders, Dream. With “He Loves Me Not,” the female pop quartet briefly inhabited TRL‘s bubblegum circuit next to the likes of Britney Spears, Christina Aguilera, Backstreet Boys and N*SYNC. Of course, this only strengthened Diddy’s relationship with the countdown show’s parent network, MTV. With the short-lived success of Dream, the CEO proved he could cater to teen pop audiences just as much as he could with his acclimated hip-hop and R&B base.

The 2000s saw Diddy transitioning from the role of a hypeman producer-turned-boastful rapper into a mogul MC finessing his A&R skills for a wider crossover appeal. Although he had a Neptunes-produced bopper lampooning his name “D.I.D.D.Y.,” his interests seemed to lie closer in media, and letting others soundtrack that journey. A few years into the new millennium, Diddy had become a more wholesome household name, on his way to amassing a near-billion dollar fortune, thanks to his Sean John clothing line (featuring signature velour sweatsuits), PG-13 rated visits on TRL (where he’d even run on a treadmill in preparation for his first New York Marathon), and reality TV programming. By 1999, the mogul was 30 but that didn’t stop him from being a tastemaker in the aughts for people in Gen X reaching their late 20s, alongside the teens and kiddy-boppers of the millennial generation (as well as some newborns and toddlers in Gen Z).

Following in the footsteps of Motown’s Berry Gordy, Diddy quickly understood that in order for Bad Boy Records to continue staying relevant, they required a hold of visual media outside the music video sphere. In 2003, the sequel to Will Smith and Martin Lawrence’s action flick Bad Boys fittingly received a soundtrack produced by the label— the project’s biggest hit being a Nelly, P. Diddy, and Murphy Lee romper called “Shake Ya Tailfeather.”

Television had experienced a new phenomenon of reality TV with shows such as Survivor and Big Brother dominating the ratings. Black moguls saw the impact of the format immediately with Diddy spearheading the movement in 2002 with Making The Band 2, a revived music talent search on MTV fulfilling what the title promised. In ways, Diddy had become responsible for creating the reality singing competition format for American TV—resulting in the co-ed hip-hop group Da Band and an infamous late-night walk across the Brooklyn Bridge for Junior’s cheesecake.

The third iteration of the series had become pinnacle MTV, a time where Diddy cofounded Citizen Change, an organization that advocated “Vote or Die” with the help of celebrity sponsors. Making The Band 3 would be responsible for establishing Danity Kane, although it’d take two seasons to finalize the quintet of Aubrey, D Woods, Shannon, Dawn, and Aundrea. They’d go on to release two studio albums before their public disbandment on live TV. Songs such as “Showstopper” and “Damaged” placed them as the answer for the void Destiny’s Child left, but also had them actively competing against The Pussycat Dolls on the charts. The male offshoot of Making The Band brought the male group Day 26 and solo singer Donnie Klang.

The mid-aughts were in developmental stages for the Bad Boy music scene. Still, the label managed to acquire a few hits and revitalize some careers. Label writer Mario Winans received a No. 2 hit with 2004’s “I Don’t Wanna Know” which, like The Fugees’ “Ready or Not,” sampled Enya’s synth-humming classic “Boadicea.” The song was blocked from the top spot by singles from Usher’s Confessions era. Ironically enough, rapper Loon warned a No. 2 single in 2002 from the first part of “I Need A Girl” with Diddy and Usher, and a No. 4 with the second installment. New Edition even captured some mild success with their Bad Boy comeback single “Hot 2Nite” in 2004.

In 2006, Bad Boy gained a resurgence and somewhat of a peak commercially. A young model from Connecticut offered a fresh pop vibe to R&B, making herself out to be a contender against the Beyoncé’s, Ciara’s, and Rihanna’s of the Hot 100. Cassie’s “Me & U” not only soundtracked the summer with a feel-good cuteness, but also made dancing in the mirror of a studio a thing for videos once again. Her eponymous debut album—which is honestly one of the most slept-on—featured the friend-zoning bop “Long Way 2 Go,” and the Ryan Leslie-penned slow grooves “Kiss Me” and “Miss Your Touch.”

Another deep cut on Cassie, “Call U Out,” featured Yung Joc of Bad Boy South. The Atlanta native quickly became a viral sensation with “It’s Goin’ Down” thanks in large part to a revving-up motorcycle dance. The song reached No. 3 of the Hot 100, cementing the pop culture phenomenon of snapping-crunk in the process and setting the wheels in motion for dances to propel hip-hop songs into new realms online—prior to Soulja Boy’s “Crank Dat.” His other single, “I Know You See It,” also had a bit of catchiness due to Joc’s nursery rhyme southern flow.

Don’t be deceived by Joc’s stint on Love & Hip Hop, as the rapper truly was the prince of the south, repping Bad Boy as if he were the Georgia spawn of B.I.G., appearing on Danity Kane’s “Showstopper” and Cheri Dennis’ “I Love You.” For his 2007 sophomore era, he’d bang with “Coffee Shop” while assisting T-Pain on “Buy U A Drank (Shawty Snappin’).” One could even credit the brute nature of Gorilla Zoe’s “Hood Nigga” to the vibes of Yung Joc’s discography.

The year also saw Diddy releasing an electronic-filled Press Play. His first three singles all featured female vocalists singing catchy hooks: Nicole Scherzinger on “Come To Me,” Christina Aguilera ripping “Tell Me,” and Keyshia Cole pouring her heart out on “Last Night.” As the millennium was starting to voyage out its first decade, Diddy had the luxury to bounce around in endeavors existing outside the music—such as the Notorious biopic and another reality TV comp, I Want To Work For Diddy—but these songs actually played a part in regenerating what constituted a radio hit for the 2010s. Nowadays, we see EDM DJs using female vocalists to drive the point of a song home, or DJ Khaled serving as the hypeman for today’s collabs. Most importantly, that work allowed for 2010’s critically-acclaimed masterpiece, Last Train To Paris from Diddy-Dirty Money (which included Danity Kane’s, Dawn Richard).

While many tend to analyze the longevity of the artists stemming from Bad Boy Records, they cease to mention how the label as a whole stayed afloat in relevancy during the aughts, and up until now. Diddy flipped inauspicious gossip upside down to preserve the label’s motto of “can’t stop, won’t stop.”

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