Top 25 Best Bad Boy Songs Of All Time

The role that Bad Boy Records played in '90s hip hop can't be overstated. From the emergence of the legendary Notorious B.I.G., to a genre-rattling beef with Death Row, to ushering in the much-maligned shiny suit era - Bad Boy was everywhere. As the vision of Sean "P. Diddy" Combs, Bad Boy had a roster positioning them as a titan in the music industry: B.I.G., Ma$e, The Lox, Faith Evans, Shyne, and many more, were a formidable team that loomed large on the rap landscape.

When the '90s ended and the jiggy era largely went with it, Bad Boy stayed relevant through reinvention. From the advent of Bad Boy South, with signees like Yung Joc and 8Ball & MJG, to the debut album of r&b siren Cassie, the label continued to crank out hits. Even up to today, with French Montana and Janelle Monáe, the label remains near the musical zeitgeist. 

Bad Boy's influence is undeniable, even in regards to what seemed clownish at the time. Putting a producer in the forefront of your videos was roundly mocked - famously so by Suge Knight - but it's a concept that artists like Pharrell ran with, and now it's a common occurrence. With Diddy as chief architect, Bad Boy sculpted an attitude, and beyond the radio hits and glossy visuals, there's an irreverence and flamboyance that's worn by his disciples to this day.

With a sprawling catalog that's adorned with classics, Bad Boy has had a run without many peers. These are the top 25 tracks in the label's diverse, consequential, and ongoing history.  

"Shot Caller" was released as French Montana's debut single with Bad Boy records. The 2012 track - whose title gives a nod to Puff's "It's All About the Benjamins" - introduced the Bronx rapper to a commercial audience, and he's been on a wave ever since. Featuring Charlie Rock, the Harry Fraud-produced track centers around a whining horn that harkens back to Bad Boy's '90s heyday. French floats on "Shot Caller" with a braggadocio befitting of his label's legacy, dropping bars throughout his verses that pay homage to the New York legends that came before him.  

The story of G-Dep is a tragic one. The Harlem rapper signed a five-album deal with Bad Boy in 1998, but was dropped just a few years later after underwhelming sales. In the early 2000s, he spiraled further into an addiction to PCP, and in 2010 he turned himself in for a cold case murder. It's a cautionary tale about the illusions of "making it", but G-Dep's short stint with Bad Boy was not without its high points. On 2001's "Special Delivery (Remix)," G-Dep brought out legends Ghostface Killah, Keith Murray, and Craig Mack on a song that further cemented Bad Boy's reign as the ruler of the remix. 

Though it's a fact that seems to fly under the radar, the multi-grammy nominated Janelle Monáe is indeed on the Bad Boy roster. The multi-faceted talent, who's seen a run of film success of late, dropped 2010's "Tightrope" as the lead single to her album The ArchAndroid. Featuring her mentor Big Boi, "Tightrope" finds Monáe delivering taut couplets about the importance of maintaining one's balance, while also offering a booming, soul-soaked chorus. It's just one standout track in a catalog of many penned by one of Bad Boy's most eclectic and daring artists. 

In the intro of "Money, Power, Respect," Lil' Kim lays out the formula for attaining the trinity of success: "First you get the money / Then you get the muthafuckin' power / After you get the fuckin' power, muthafuckas will respect you." It's an ethos in line with where Bad Boy was at in 1997, but instead of being packaged as a glossy, flexing radio hit, "Money, Power, Respect" is a grittier, outright dark song. The first single from the Lox' debut album of the same name, "Money, Power, Respect" also features a DMX in his prime, and all five rappers on the track pull no punches about the dirt required to reach those three tenets of triumph.

Puffy's experimental r&b project Diddy - Dirty Money is a testament to the mogul's ability as a tastemaker. When the group - which featured singers Dawn Richard and Kalenna Harper - released Last Train to Paris in 2010, it was a bold, Euro-house inspired outing that was altogether different from mainstream r&b of the time. Filled with moments of coldness and sleaze, Last Train to Paris did as much to influence the current wave of alternative r&b as the oft-cited genre touchstone 808s and Heartbreak. On the album's sixth single "Ass on the Floor," Swizz Beatz' drum march production offers the perfect bed for a song about soldiering through a night at the club with a broken heart. Complete with a chorus that's more cynical than optimistic, "Ass on the Floor" is one of Diddy's most creative and underrated songs.

With the formation of Bad Boy South in 2004, Diddy sought to expand his empire into a region that was starting to blow up nationally. By recruiting veterans 8Ball & MJG, Bad Boy's southern imprint had an instant credibility, and their first album for the label, Living Legends, remains the duo's highest charting effort to date. The lead single from the Memphis rappers' Bad Boy era, "You Don't Want Drama," features a synth-heavy, early-Bangladesh beat, and 8Ball & MJG give a clear warning that they're not beyond going to the trunk.

"Cupid" was the third single off of 112's 1996 album of the same name. It was the group's second full-length effort, and would eventually go platinum as another highlight in the Atlanta r&b quartet's massive run of success in the '90s. On a slow, acoustic guitar-driven track, "Cupid" sees 112 singing about the creeping doubt that comes with diving into a new relationship, all while offering a chorus to calm that prospective lover's fears: "Cupid doesn't lie, but you won't know unless you give it a try."

1995's "Can't You See" was the debut single from Total, Bad Boy's first r&b group. The New Jersey trio had previously provided vocals for the Notorious B.I.G.'s first single "Juicy, so the Brooklyn legend returned the favor in kind. With Biggie offering a blistering verse as an intro, the Puff Daddy-produced track segues into a more lush, slow tempo anchored around a sample from James Brown's "The Payback. Total's rich, textured vocals on "Can't You See" would prove to be a preview, as the group went on to feature on numerous top-10 singles in the '90s.

2001 saw Bad Boy founder Puff Daddy re-brand as P. Diddy. It was a move that cleaned the slate for an artist who watched the '90s end with a series of lows: the death of the Notorious B.I.G., an assault charge after a run-in with Interscope's Steve Stoute, and the 1999 Club New York shooting that put Shyne behind bars for the next decade. "Bad Boy For Life," the second single from The Saga Continues..., finds the newly minted P. Diddy triumphantly announcing "It's official, I survived what I been through," on a track that features then-Bad Boy signees Black Rob and Mark Curry. Over a beat by Megahertz that surges around a sampled guitar riff, P. Diddy is a man re-charged, who, even through all the drama of the years prior still maintains that it's Bad Boy for life. 

Faith Evans' "Love Like This (Remix)" remains a ubiquitous r&b song to this day. That signature guitar lick and disco bass line sample seems to play in the background of TV shows and commercials in perpetuity. The uptempo track - a remix to the lead single from her 1998 album Keep the Faith - displays Bad Boy's premier songstress near the top of her game, celebrating the optimism that comes with new love. Garnished with a Black Rob verse that sees the rapper whisking away his girl, this is one of Bad Boy's more heartfelt, yet danceable remixes.  

During his time on Bad Boy in the '90s, Black Rob featured on a lot of remixes, but didn't get much of the spotlight to himself. The Harlem rapper finally got his due in early 2000, when he released "Whoa!," the lead single to his platinum-selling album Life Story. Produced by Buckwild, "Whoa!" uses a chopped orchestral sample and heavy drums to underline Black Rob's gravely, abrasive flow. With every line ending in the word "whoa" - a 99 Benz Coupe is whoa; C.O.'s and P.O.'s are not - the song has a catchy design, and it remains a highlight in the Bad Boy catalog. 

A sultry, late-night r&b track with a minimalist keyboard riff, Cassie's debut single "Me & U" was a radio constant in 2006. Written and produced by Ryan Leslie, "Me & U" introduced the world to Cassie, whose haunting vocals hang over the sparse instrumental, punctuating the occasional surging bass line with a hit-magnetic hook. It's an r&b song that's a throwback to an electro-addled '80s, and it was a major success, spending almost five months in the Top 40. "Me & U" is a crown jewel of the mid-2000s Bad Boy era, and it's also just a dope song from an artist we don't hear enough from. She also happens to be Diddy's current bae.

Produced by Mario Winans and P. Diddy, 112's "Peaches & Cream" has one of the most recognizable r&b beats of the past 20 years. With distorted synths and an electro-bounce feel, the song is a relic of its time, a track not dissimilar to what saw Timbaland and the Neptunes flooding the radio in the early 2000s. An after-hours thirst anthem with few moments of subtlety, "Peaches & Cream" would go on to be 112's highest charting single, even snagging a Grammy nomination in 2002 for Best R&B Performance by a Group or Duo.

By the mid-2000s, Atlanta was well on its way to becoming the center of the rap universe. With the creation of Bad Boy South, Diddy had designs on solidifying the future of his empire, and with the signing of A-Town's Yung Joc, the new imprint got its first major hit. The lead single from 2006's New Joc City, "It's Goin' Down" became a snap anthem that hit #3 on the Billboard Hot 100 chart. The Nitti-produced track has stood the test of time, with some of Joc's more memorable lines popping up in other rappers' verses to this day.

"Lookin' at Me" was the third single from Ma$e's 1997 album Harlem World. It's a song with an eerie atmosphere - dark synths pulse over punchy drums, and Ma$e raps with near-paranoia about those monitoring his successes. Puff Daddy, for his part, offers a quiet, whispery hook that furthers the track's altogether different feel from typical Bad Boy fare of that time. The then-unique sonic aspects of "Lookin' at Me" can be credited to the Neptunes, who at that point were still a relatively unknown production tandem. 

Shyne's debut single "Bad Boyz" hit like a punch to the jaw. The first offering from the Brooklyn rapper, an eponymous shoutout to his label, remains the most viscerally impactful effort from a Bad Boy signee not named Christopher Wallace. Over a booming beat by EZ Elpee - whose piercing drums are matched by a thundering piano riff - Shyne introduces himself without mincing words: "Now tell me who wanna fuck with us? Ashes to ashes, dust to dust / I bang - and let your fuckin' brains hang, snitches."

Complimented by legendary singer Barrington Levy, Shyne's gritty flow flashed on a track that should've ushered in a new flagship artist for Bad Boy. Unfortunately, after taking the rap for a 1999 shooting incident, Shyne spent the next nine years in prison, leaving a major question mark on what could have been

Originally a B-side to the 1995 single "Big Poppa", the Notorious B.I.G.'s "Who Shot Ya?" went on to have a controversial life of its own, as many have interpreted the song to be about Death Row rapper 2Pac. The then-rival west coast rapper had been shot in New York just one month prior to the song's release, and B.I.G.'s evocative, violent lyrics seem to imply a specific target: "You'll die slow but calm / Recognize my face, so there won't be no mistake / So you know where to tell Jake, lame nigga / Brave nigga, turned front page nigga."

Whether or not the song was influenced by his burgeoning beef with 2Pac remains up for debate, but "Who Shot Ya?" has held up as a lasting tribute to Biggie's lyrical dexterity and ability to conjure an image.

"Hypnotize" has the unfortunate distinction of being the last song released during the Notorious B.I.G.'s lifetime. The lead single from his album Life After Death, the record made it to stores on March 1, 1997, just one week before the rapper was gunned down in Los Angeles. Though it's a song that's irrevocably tied to an untimely death, "Hypnotize" is an upbeat, jubilant track whose booming bass line and catchy hook has kept it in rotation for over 20 years. Produced by Puff Daddy and D-Dot, "Hypnotize" would be Biggie's first #1 single, an accomplishment he sadly didn't get to witness.

A tribute to the fallen Notorious B.I.G., "I'll Be Missing You" was the second single from Puff Daddy's 1997 album No Way Out. With a memorable sample from the Police's 1983 hit "Every Breath You Take", "I"ll Be Missing You" has a somber, heartfelt tone that earnestly reflects a man who misses his friend. Calling on Bad Boy's stable of capable crooners, Faith Evans and 112 offer affecting vocals to bookend Puff's forlorn verses. "I'll Be Missing You" remains Diddy's biggest hit, claiming several Grammy Awards and spending a staggering 11 weeks atop the Hot 100.

A funk sample-driven, club-friendly anthem about the perils of prosperity, "Mo Money Mo Problems" saw Bad Boy at the zenith of their success. The second single from the Notorious B.I.G.'s Life After Death, the 1997 radio mainstay would be the rapper's second posthumous #1 hit - a feat that had not been previously accomplished. Beyond being a pop smash, the glitzy, Hype Williams-directed visuals for "Mo Money Mo Problems" perfectly captured the Bad Boy aesthetic of the time: joyful, shiny, and on top of the world.

Though Puff had by no means shied away from the spotlight, it wasn't until 1997's No Way Out that he really put himself forward as a rapper. His debut album would be certified platinum seven times, proving he was more than viable commercially, and it all kicked off with his lead single "Can't Nobody Hold Me Down". With a fitting title for a behind the scenes artist thrusting himself into the limelight, "Can't Hold Me Down" relied on an iconic Grandmaster Flash sample as the vehicle for Puff's message: "You name it, I could claim it / Young, black, and famous, with money hangin' out the anus."

Ma$e's 1997 hit "Feel So Good" was a quintessential late '90s Bad Boy experience. The anthemic party staple - which samples Kool & The Gang and Miami Sound Machine - had considerable pop appeal, charting as high as number 5 on the Billboard Hot 100. Visuals for "Feel So Good" were also par for the course in that era of Bad Boy: directed by Hype Williams, a wardrobe of shiny suits, and a few celebrity cameos. This track remains the biggest hit of Ma$e's career, and it's not unusual to hear its familiar bass line coming from car stereos to this day.

There are few early '90s rap songs as instantly recognizable as Craig Mack's "Flava in Ya Ear (Remix)". With Puff Daddy's rendition of a famous scene from The Warriors, followed by a stuttering horn sample that kicks in to a stellar B.I.G. verse, this 1994 classic opens hard and delivers throughout. Serving as the remix and B-side to the Craig Mack single - which was Bad Boy's first-ever release - the track features Biggie, LL Cool J, Rampage, and Busta Rhymes. Boasting a loaded lineup, the "Flava in Ya Ear (Remix)" shows each rapper going in over one of the greatest Bad Boy beats of all time.

Released in 1994 as the debut single from the Notorious B.I.G., "Juicy" is considered by many to be one of the greatest hip hop songs of all time. Over a bouncing drum-centric beat produced by Puff Daddy and Poke of the Trackmasters, Biggie glides effortlessly, detailing in vivid imagery the story of his come-up. Announcing in defiance on the track's info that "This album is dedicated to all the teachers that told me I'd never amount to nothin'", B.I.G. goes on to lay it all out in breakneck pace: looking up to rappers as a youth, the perils of drug dealing in his teens, and eventually sold out shows and condos in Queens. Beyond being a stunning song by a genius rapper, it's one of the best pieces of American art about truly going from rags to riches. 

"It's All About the Benjamins" was yet another watershed moment for Bad Boy's influence on pop culture. The 1997 single from Puff Daddy's No Way Out found the word "Benjamins" becoming commonplace slang, while the track itself shot to #1 on the Hot 100 chart. Featuring the Notorious B.I.G., Lil' Kim, and the Lox, "It's All About the Benjamins" showcases the label's flagship artists over an almsot menacing Deric "D-Dot" Angelettie beat. Emblematic of a cultural shift happening in hip hop in the late '90s, "It's All About the Benjamins" is a matter-of-fact song about flaunting cash and reveling in prosperity.