30 Must-See Pictures Of Bad Boy Artists Over The Years

Sean Combs, also known as Puff Daddy, established Bad Boy Records after being fired from his role at Uptown Records. Combs’ vision was to create a label that would not only discover raw talent but also shape the musical landscape. One of the label’s most significant milestones was the release of The Notorious B.I.G.‘s debut album, Ready to Die, in 1994. The album featured hits like “Juicy” and “Big Poppa” and solidified Biggie as a force in the rap world. This debut is often credited with putting Bad Boy Records on the map. RELATED: New Evidence Has LAPD Looking at Diddy For the 1996 Shooting of Tupac RELATED: Diddy Accused Of Threatening Former “VIBE” Editor-In-Chief Danyel Smith Over Magazine Cover In the same year, Craig Mack released his hit single “Flava In Ya Ear,” which became an anthem and further established Bad Boy Records as a major player in the industry. The remix of the song, featuring artists like LL Cool J and Busta Rhymes, became iconic within hip-hop culture. Bad Boy Records reshaped the music industry by blending hip-hop with pop sensibilities, creating chart-topping hits and timeless classics. The label not only introduced some of the most memorable artists of the 90s and 2000s but also set new standards for music production, marketing, and cross-genre collaborations.

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Today, Bad Boy Records remains a cultural touchstone, symbolizing innovation, resilience, and the enduring power of music to influence and inspire.

1. The Notorious BIG & Sean Combs On 'Hypnotize' Set

American rapper Notorious BIG (also known as Biggie Smalls, born Christopher Wallace, 1972 – 1997) (left) and Sean Combs (also known as Puff Daddy and P Diddy) on the set for the former’s ‘Hypnotize’ music video, Los Angeles California, February 1997.

2. The Notorious BIG & Sean Combs During Video Shoot

View of American rapper the Notorious BIG (born Christopher Wallace, 1972 – 1997) (left) and Sean Combs as they talk together on the set of the ‘Can’t You See’ music video (performed by Total), New York, New York, circa 1995. 

3. Mario Winans, Harve Pierre, Cassie, & Diddy Partying Together.

Mario Winans, Cassie, Asim, Yung Joc, Elphant Man,Harve Pierre and Sean Diddy Combs 

4. Danity Kane for Dollhouse

Danity Kane for Dollhouse

5. Diddy’s Da Band

Da Band during Sean P. Diddy Combs Introduces the Release of Da Band’s Album Too Hot for TV at Circuit City in New York City, New York, United States.

6. Don’t You Miss This Lil Kim?

Rapper Lil Kim (Kimberly Denise Jones) performs during the Big Beat/Atlantic Records showcase at the Impact Music Convention at the Fontainebleau Hilton Hotel in Miami Beach, Florida in April 1997.

7. Faith Evans

NEW YORK – OCTOBER 5: American singer Faith Evans poses for a photo backstage at Madison Square Garden for Lifebeat’s Urban Aid benefit concert on October 5, 1995 in New York City, New York. 

8. Remember Vote or Die?

Sean “P Diddy” Combs (L) with supporters outside an MTV event in Times Square for Combs’ “Vote or Die” campaign.

9. Rapper Loon & Carl Thomas

Carl Thomas, P Diddy Combs and Loon in the press room at the 2003 VMA’s at Radio City Music Hall.

10. Diddy & Black Rob

Sean (P. Diddy) Combs, right, poses with Black Rob at the midnight album release of Combs” latest CD at Virgin Mega Store in Times Square July 9, 2001 in New York City. 

11. Diddy & Day26

Day 26 and P. Diddy perform at MTV’s “Making The Band 4: The Final Chapter” live finale at The Hudson Theatre on April 23, 2009 in New York City. 

12. G-Dep and Black Rob

G-Dep and Black Rob during Don Pooh’s Birthday Party – August 21, 2003 at Club Exit in New York City, New York, United States. 

13. The Lox & Diddy Reunited

Sean “Diddy” Combs aka Puff Daddy (R) performs onstage with The LOX during the Puff Daddy and The Family Bad Boy Reunion Tour presented by Ciroc Vodka and Live Nation at Barclays Center on May 21, 2016 in New York City.

14. The Crew

Craig Kallman, Mario Winans, Sean “Diddy” Combs, Harv Pierre, Stephen Hill, Mike Kyser and Kevin Liles attend Day26’s “Day26” album release party at Room Service March 24, 2008 in New York City.

15. The Dynamic Duo

Mase (born Mason Betha) (left) and Sean Combs attend the 11th annual Nickelodeon Kid’s Choice Awards at UCLA Pauley Pavilion, Westwood, California, April 4, 1998. 

16. 'Can't Nobody Hold Me Down'

Sean Combs (left), performing as Puff Daddy, and Mase (born Mason Betha) on the set of the ‘Can’t Nobody Hold Me Down’ music video, Apple Valley California, 1996. 

17. Craig Mack & Notorious B.I.G.

Rappers Saafir, Craig Mack, The D.O.C. and late rapper Notorious B.I.G., pose for photos backstage after their performances at the Riviera Theater in Chicago, Illinois in SEPTEMBER 1994. 

18. Shyne at Jennifer Lopez Record Release Party

Shyne poses at the Jennifer Lopez record release party in New York City May 26, 1999.

19. Remember Donnie Klang?

Sean “P. Diddy” Combs poses for a photo with the winner of “Making The Band Season 4” Donnie Klang backstage during MTV’s “Making The Band 4” finale at the MTV Times Square Studios August 26, 2007 in New York City. 

20. Remember When Que and Dawn were a thing?

Singer Dawn Richard and Day26’s Que enjoying CIROC lemon cupcakes at the White Party hosted by Sean “Diddy” Combs and Ashton Kutcher to help raise awareness for Malaria No More held at a Private Residence on July 4, 2009 in Beverly Hills, California. (

21. Clive Davis, Faith Evans, & Sean Combs

Clive Davis, R&B singer Faith Evans, and rapper & music executive Sean Combs on the set of one of Evan’s music videos, New York, New York, circa 1995. 

22. Lil Kim and Lil Cease

Lil’ Kim & Lil’ Cease during 15th Annual Rock and Roll Hall of Fame Induction Dinner at the Waldorf Astoria in New York City, New York. 

23. 112, The Notorious BIG, & Lil' Kim

R&B group 112 and American rappers Notorious BIG (also known as Biggie Smalls, born Christopher Wallace, 1972 – 1997) (second left) & Lil Kim (born Kimberly Jones) (center fore) as they pose at an unspecified restaurant, New York, New York, circa 1996. 

24. Even Though Lil Kim Wasn’t Officially Signed To Bad Boy, She Was Definitely An Honorary Member.

Lil’ Kim (aka Kimberly Jones) was arrested by New Jersey cops in July 1996 and charged with possession of marijuana.

25. Total

Singers Keisha, Kima and Pam from Total poses for photos backstage at the South Shore Country Club in Chicago, Illinois in February 1996. 

26. Diddy & J. Lo

Los Angeles, CA, February 21, 2000 ? MTV: MUSIC TELEVISION brought together Grammy?nominated artists for a special edition of ‘Total Request Live’ and a unique photo shot by David LaChapelle. Many of these artists became stars or enjoyed even greater popularity through their exposure on ‘TRL.’ The ‘TRL’ class photo will be turned into a poster and sold via MTV.com with proceeds going to charity. L?R: Sean ‘Puffy’ Combs, Joey Fatone of ‘NSYNC, and Jennifer Lopez pose for the photo.

27. 8 Ball, MJG and Sean "Diddy" Combs

8 Ball, MJG and Sean “Diddy” Combs 

28. Diddy, Biv and Ronnie DeVoe

New Edition during Post VMA Party Hosted by Sean “P. Diddy” Combs and Guy Oseary 

29. Notorious B.I.G. AKA Biggie Smalls Receives Billboard Music Award.

Rapper Notorious B.I.G. AKA Biggie Smalls (Christopher Wallace) joined by Sean (Puffy) Combs and Lil’ Kim receives Billboard Music Award on December 6, 1995 at The Coliseum in New York City, New York. 

30. Diddy Performing “Missing You” With Sting.

Sting and Puff Daddy at MTV Video Music Awards held in Radio City Music Hall, New York City on September 04, 1997