The 21 Flashiest Videos From Puff Daddy's Bad Boy Records

While other '90s music dynasties have floundered, Bad Boy endures. And thanks to the magic of YouTube, know what else endures? The label's flashy videos.

Even if you don't own the suit Jadakiss wore on the cover of Money, Power & Respect, if you spent any time watching MTV, BET, or VH1 in the late '90s, you probably spent some time luxuriating in the opulent excess of the the Bad Boy empire. But there was more to the label's output than questionable fashion choices: over 20 years, directors like Hype Williams, Spike Jonze, Wendy Morgan, and Colin Tilley have given the label a visual style that's as distinct as it is impossible to pin down.

Rhino released the Bad Boy 20th anniversary box set on August 12th, and in the fall, company impresario Puff Daddy will lead the Bad Boy family on a reunion tour to celebrate the notorious hip-hop and R&B label's two-decade-plus run as a groundbreaking, shiny suit-rocking force in modern music. Watch these classic clips to pay your respects -- we guarantee they'll make you feel so good. 

"Juicy," Notorious B.I.G. (1994)

Though the iconic video for "Juicy" starts with a street-level view of Biggie as a sardine-eating, Word Up magazine-reading young man, it quickly reaches the dizzying heights of pool party-throwing, contract-signing rap superstardom. Cutting between a real struggle and a utopian party, the video succinctly introduced an artist who personified hip-hop's fiery contradictions. "Stereotypes of a black male misunderstood," he raps. "And it's still all good." Fittingly, one of the best rap songs of all time got the video to match.

"Big Poppa," Notorious B.I.G. (1994)

Dressed in a turtleneck, suede jacket, and Kangol, Biggie looks as cool as ever in this clip, but he's probably a little sweaty in that outfit, right? While a lot of the best Bad Boy videos take you on speedboat rides through coastal vistas, "Big Poppa" is all pink-lighted nightclub interiors, tableside chats, and shots of Puff in the bathtub. And, yes: it's way better than that video of Barney rapping along to the song

"Flava in Ya Ear (Remix)," Craig Mack feat. Rampage, LL Cool J, Busta Rhymes, Puff Daddy, and Notorious B.I.G. (1994)

With its Warriors-referencing, bottle-clinking opening, stark black-and-white photography, and raw performances from stars like Busta Rhymes and LL Cool J, this Hype Williams video remains an unassailable slice of East Coast cool. While future Bad Boy videos had bigger budgets and more extensive hair-and-makeup departments, none had the same effortless swagger as this one. (Years later, Brooklyn rapper Mister Muthafuckin' eXquire would pay tribute to the original video with his remix of "The Last Huzzah," featuring Das Racist, Despot, El-P, and Danny Brown, a worthy follow-up to the original's gonzo energy.)

"You Used to Love Me," Faith Evans (1995)

You can't talk about the "First Lady of Bad Boy" without talking about the video for "You Used to Love Me." This is some dramatic Lifetime movie shit: Evans' real-life philandering husband Biggie hosts a radio show, and a woman calls in saying she's having man trouble with her cop boyfriend (played by future Grey's Anatomy star Isaiah Washington), and then she leaves her phone on a chair and climbs out on a window ledge. You think she's going to jump, but no… she's rescuing her cat! And then her no-good cop boy toy busts inside the apartment and they embrace, providing a happy ending to one of R&B's saddest songs.

"No One Else (Remix)," Total feat. Foxy Brown, Lil' Kim, and Da Brat (1996)

How excessive was the music business in the '90s? It was not a rare thing for a song to have multiple videos. R&B group Total's "No One Else" single got a Hype Williams-directed video for its first go-around, then got an even better bank-robbery narrative clip for the remix. It's like Set It Off, but with Foxy Brown, Lil' Kim, and Da Brat executing the perfect heist in tough leather outfits. But these rappers were not thick as thieves: Foxy Brown and Lil' Kim have beef, and this is the only song they teamed up on.

"Hypnotize," Notorious B.I.G. (1997)

You know you're watching a killer video when you see the words "Florida Keys" right at the beginning and spot a speedboat in the distance. In the post-"I'm on a Boat" era, rapping on a boat has become a video cliché, but when "Hypnotize" dropped, Puff and Biggie were nautical pioneers, doing their Starsky and Hutch routine on the high seas as helicopters chased them in the distance like something out of a James Cameron movie. It's, in a word, hypnotizing.

"Mo Money Mo Problems," Notorious B.I.G. feat. Mase and Puff Daddy (1997)

Now things get really crazy. Putting aside the golf interludes, this video is a beautiful vision of a future where all surfaces are reflective. Hype Williams must've shown up on set and been like, "Let's remake 2001: A Space Odyssey with yellow goggles and a unisphere!" What could have been a melancholy video -- the Notorious B.I.G. died before they shot it and is relegated to old live footage on his own song -- becomes a joyous retro-future masterpiece.

"Feel So Good," Mase (1997)

It took all my restraint not to fill this list with Mase videos -- seriously, check out the clip for "24 Hours to Live" if you've never seen it -- but "Feel So Good" is the shiny-suit tone poem that will have to serve as a stand-in for all of them. Seriously, so many shiny suits! Few things give me more joy than watching Mase, Puff Daddy, and Chris Tucker dance around in those silver outfits under the gaudy lights. "I dress with what I was blessed with," raps Mase. Mase never lies.

"Sky's the Limit," Notorious B.I.G. (1997)

How do you make Biggie videos without Biggie? The tragic death of Christopher Wallace in 1997 left his label with a series of challenges when promoting his posthumous double album, Life After Death. Skate rat-turned-video auteur Spike Jonze had perhaps the most poignant solution, casting children as all the major Bad Boy players in a hip-hop version of Bugsy Malone. It's a cute idea, elevated by the decision to play the concept completely straight. Jonze would go on to use the same approach in Being John Malkovich, Adaptation, and Her. Totally commit to the absurdity of the premise. Never wink.

"Money, Power & Respect," The Lox feat. DMX and Lil' Kim (1998)

The visceral hardcore intensity of The Lox made them stand out from the rest of the Bad Boy roster -- there's a reason why they wanted to sign to Ruff Ryders so bad -- but that same grittiness was exactly what made their ascent so exciting. The video for the title track off their debut LP finds the trio of Sheek Louch, Styles P, and Jadakiss subtly pushing against the slick packaging of making a major-label rap video. Sure, it's got cheesy dramatic interludes with slow motion and a really boring car chase, but the focus is on the three stars wearing leather gloves and rapping into the camera like they want to rip your face off. And they will.

"It's All About the Benjamins," Puff Daddy feat. Lil' Kim, The Lox, and Notorious B.I.G. (1997)

Again, we've got two videos to choose from: there's the original version, with Puff tap dancing and running through the woods in a white suit, and then there's the prom-themed "rock remix" directed by Spike Jonze. Personally, I prefer the original -- give me Jadakiss and Lil' Kim over Dave Grohl and Rob Zombie any day -- but both paint a portrait of Puff as king, a fearless genre-mixer at the top of his game. He was all about the Benjamins, but he was also all about making good videos. 

"Been Around the World," Puff Daddy feat. Mase and Notorious B.I.G. (1997)

Who has time to watch a 10-minute music video nowadays? Only an artist like Beyoncé is capable of demanding that type of attention, but in 1997, Puff Daddy had enough pull to get people excited about an "extended video" that also feels like an '80s spy comedy. A partial list of the video's crimes: Quincy Jones has a cameo as "Agent Q," Jennifer Lopez plays a princess, and the whole thing ends with Puff mowing his lawn with one of those old rotary mowers. The song doesn't even start till almost four minutes into the video!

"I'll Be Missing You," Puff Daddy feat. Faith Evans (1997)

In an essay naming Biggie the "artist of the year," Spin's Charles Aaron described this Hype Williams-directed video for the megahit "I'll Be Missing You" as "tragically absurd," and there's still no better way to put it. Watching Puff ride his motorcycle, plead into the bright sky, and brood under the lights of that one tunnel in O'Hare Airport as that "Every Breath You Take" sample wails on will always feel ridiculous. But it lives on: just this year, TheDaily Show parodied the video to pay tribute to Ben Carson's dead presidential campaign. It remains the bad video you reach for in your darkest hours.

"Peaches and Cream," 112 (2001)

While Puff and Biggie were the larger-than-life superstars, the R&B roster of Bad Boy has always been the label's not-so-secret weapon, providing hit after hit in a genre that values consistency and longevity over flash. 112 will probably never get enough credit for delivering catchy, club-ready hits, but the neon video for "Peaches and Cream," one of the best food-related songs of all time, brilliantly makes the case for the group as neo-soul gods. Put on your tracksuit and enjoy.

"I Don't Wanna Know," Mario Winans (2003)

It's wild that the same Enya song was sampled in two classics: the Fugees' "Ready or Not" and this moody R&B ballad. If you thought all Enya could do was transport you back to Middle Earth with one note of her ethereal voice, then you need to watch this video. It's all anguish and heartbreak, the type of clip that will send you reaching for a Lord of the Rings DVD box set just to dull the pain. Mario Winans would never score a syrupy hit like this again, possibly because he used up all his tears here. Cheer up, Mario. 

"You Don't Want Drama," 8Ball and MJG (2004)

While Bad Boy will always be associated with New York, Puff Daddy was a savvy enough entrepreneur to recognize that hip-hop was bigger than two rival coasts. With the signing of Memphis veterans 8Ball and MJG he created Bad Boy South, and this raucous video was a fired-up introduction to the group's innovative, minimal crunk music. Like any good Bad Boy video, it feels like a party teetering on the edge of total chaos.

"Me & U," Cassie (2006)

The video for Cassie's space-pop hit "Me & U" is filled with sweaty, sexy dance rehearsal footage that captures the song's teasing, sensual energy. Can you believe there's an even more salacious version out there? In the more explicit video that the young singer's management later disavowed, claiming it was only intended for European audiences, Cassie strips down to her underwear and unbuckles a man's pants in a seedy-looking POV shot. And then Puff Daddy appears at the end for some reason? It's, uh, confusing.

"Damaged," Danity Kane (2008)

It's tough to talk about the legacy of Puff Daddy without mentioning the Making the Band era and Dave Chappelle's brutal parody of it. But the bizarre, often mind-numbing MTV reality show gave us more than a classic sketch: it gave us Danity Kane and the bubblegum fever-dream of the "Damaged" video. It's a video that answers the question, "How much pink light can you stare at without damaging your retina?" The answer: this much. 

"Ass on the Floor," Diddy-Dirty Money feat. Swizz Beatz (2010)

If any Diddy record is destined to be rediscovered and celebrated decades from now as his underrated "cult record," it will be Last Train to Paris, a forward-thinking alt-R&B curio from 2010. Amid icy neo-soul, spacey techno, and arty house flourishes, Diddy and his collaborators gave us one drum-and-synth-driven banger to play in the club. The Colin Tilley-directed video is a chilly dance party on the planet Hoth, with women wearing fur coats and skimpy outfits as snow falls around them. It's filmmaking as snowglobe-building, like an R-rated ride on the Polar Express with Cîroc instead of hot cocoa.

"Tightrope," Janelle Monáe feat. Big Boi (2010)

Janelle Monáe isn't just an anomaly in the Bad Boy family, she's an anomaly on this planet. The David Bowie- and Prince-inspired R&B singer-songwriter makes epic, Afrofuturist concept albums about robots, but she's never been more accessible than on "Tightrope," the breezy, toe-tapping single from her major-label debut, The Archandroid. With her stylish pompadour, immaculate tuxedo, and deadpan grace, Monáe dances right into your heart.

"Pop That," French Montana feat. Rick Ross, Drake, and Lil Wayne (2012)

As a hip-hop hit-making entity, Bad Boy has seen better days. Puff Daddy still reigns over New York as a seemingly untouchable Sinatra-like figure, and his recent music is more inventive than that of his many aging peers like Dre, Snoop, and Jay Z, but the label is hardly the powerhouse it once was. Occasionally an artist captures the old feeling, and nowhere is that more apparent than in the absurd bikini party video for "Pop That," by Bronx-based shouter and Khloe Kardashian ex French Montana. It's catchy enough to make you open your closet and start looking for that shiny suit you sent to the cleaners.

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Dan Jackson is a staff writer at Thrillist Entertainment, and like Mase, he wants TVs in the headrest. He's on Twitter @danielvjackson.