Wild Facts About Sean Combs, A Bad Boy For Life

September 27, 2023 | J. Clarke

Wild Facts About Sean Combs, A Bad Boy For Life

Rappers often take heat for making unsavory music about women, substances, and worse. Sometimes it’s all a show, but when it comes to the life of Sean Combs, that barely scratches the surface of all the horrors he survived on his way to stardom.

1. He Was Born In The Struggle

Both Combs’ parents worked decent jobs before they had him in 1969. His mother worked in education, while his father served in the military. Tragically, this didn’t necessarily translate to their living conditions. They had Combs in Harlem, New York.

The poor neighborhood made for a childhood characterized by hard times.

Sean Combs P.Diddy looking at the cameraVahan Stepanyan, Shutterstock

2. He Hated It

Combs grew up well acquainted with some of the roughest, toughest ways to live. He remembered times when he woke up to roaches on his face, and other times when the stench in his home became unbearable. Living in these conditions didn’t serve the young boy at the time—and neither did his father’s post-military profession.

Sean Combs (P. Diddy) attends the Grammy after partyDooley Productions, Shutterstock

3. His Father Worked The Streets

Although it didn’t become completely clear to him until he started to grow up, Combs’s father sold drugs. He wasn’t just a small fry, either. People in Harlem knew him well for what he did, especially among other men who did the same. As expected, though, the risky lifestyle soon caught up with him in the most tragic way possible.

HarlemMomos, Wikimedia Commons

4. They Took His Dad From Him

In 1972, someone fatally shot his father while he sat in his vehicle. His mother Janice couldn’t bear to tell him the truth. She instead told her son that his father passed in a car accident. Likely fearing for his future, Combs’s mother decided he needed a radical change if he’d ever have a real chance at life.

Sean Robert Mecea, Getty Images

5. She Took Him Away

Janice moved herself and her son to Mount Vernon, New York, and worked several jobs to provide for him there. This didn’t totally keep him away from the dangerous streets of his birthplace, though.

Members of his family still lived in Harlem, and he visited often. It’s also where he got a nickname that became a major part of his brand.

Mariah Carey, Sean KMazur, Getty Images

6. He Had A Temper

Notoriously so, Combs changed his stage name (and eventually his actual name) multiple times during his career. His first, though, came from his childhood anger. When he got upset, he’d “huff an puff”. This led his loved ones to start calling him “Puff”. The name would help him rise to the top of the hip hop world—but his start in the industry was far from smooth.Sean John Combs p. diddy looking at cameralev radin, Shutterstock

7. He Dropped Out

Despite the challenges of his childhood, Combs graduated high school and began studying business at Howard University in the late 1980s. There’s not much record of his time there, and with good reason: He dropped out after only two years. He knew what he wanted to do, and it wasn’t school.

Combs turned his attention to the music world—not knowing what lurked beneath the glitter.

Howard UniversityFourandsixty, CC BY-SA 4.0 , Wikimedia Commons

8. He Started Small

Combs started as an Uptown Records intern in 1990. But he wouldn’t stay at the bottom for long. He soon found himself working with big music industry names like Mary J. Blige and Jodeci. Uptown quickly realized Combs had what it takes. In fact, he soon found himself producing on a record that went on to sell millions. He was good—and he knew it all too well.Sean Combs at a recording studioAl Pereira, Getty Images

9. He Wanted The Kingdom

The young Combs had direct access to the head of the label, Andre Harrell. While their relationship seemed to start as a mentorship, Combs’ passion quickly got the best of him. He began pushing his own agenda at the label, and he started to butt heads with Harrell.

But Combs had come too far to turn back now.Andre Harrell and  Sean Al Pereira, Getty Images

10. He Lost His Job

Harrell fired him in 1993. Getting fired usually seems like a loss, but it proved to be only the beginning for Combs. He started his own label that same year, Bad Boy Records. He signed the Notorious B.I.G. and got to the work of making hits.

While his career began to take off, major changes in his personal life came as well.The Notorious BIG & Sean Combs PerformingNitro, Getty Images

11. He Started Young

As if starting a record label wasn’t enough on his plate, Combs welcomed his first child in that same year. With his work taking up so much of his life, his son ultimately spent most of his time with his mother, Combs’s high school love Misa Brim.

As far as Combs’ love interests go, however, there isn’t much to share on Brim. The really fiery relationships came later.

Misa Hylton-Brim, Justin Dior Combs and Sean Patrick McMullan, Getty Images

12. He Fell Hard

The first time Combs laid eyes on Kim Porter, she was actually with her ex-boyfriend. They didn’t fall in love in an instant, but Combs found himself enamored with her presence. They officially began dating in 1994 and had their first baby in 1998.

Amidst all this romantic bliss, however, something scary brewed beneath the surface.

Kim Porter and Sean Carmen Valdes, Getty Images

13. He Had Beef

The rise of Bad Boy Records coincided with a riff that grew between West Coast rappers (most famously Tupac) and East Coast rappers (like Combs’s own B.I.G.). The diss tracks and publicity likely heightened his success, Puff Daddy threw his own hat in the rap ring in 1997.

He dropped his first rap album, No Way Out, and saw huge success—along with huge trouble. 

Tupac Shakur in movieColumbia Pictures, Poetic Justice(1993)

14. He Lost His Diamond

In that same year, just six months after Tupac’s tragic shooting, his biggest rival, the Notorious B.I.G. met the same fate, and Combs’ entire world came crashing down. Still, Combs turned the tragedy into a hit, releasing “I’ll be Missing You” in B.I.G.’s honor.

Hits and sales aside, though, some people hated what he did to the Hip Hop genre.

Notorious B.I.G.The Come Up Show, Flickr

15. He Wasn’t Legit

Combs’ label continued to rake in the cash. Unfortunately, not everyone found his music impressive. In fact, many people thought he did the whole genre a disservice. He faced criticism for making Hip Hop too commercial, among other things.

But that didn’t quite compare to the mess he made of his own relationship.

Rapper and producer Sean 'Puffy' Combs (Sean John Combs) in white looking at cameraRaymond Boyd, Getty Images

16. He Had Wandering Eyes

Both Jennifer Lopez and Combs grew up in New York City, but they first met when they were working together. Lopez, music artist and burgeoning actress, performed in Combs’s music video “Been Around the World”. The “Bad Boy” producer is on record saying it was love at first sight.

It’s a good time to note that the two met in 1997…remember that for what’s coming next.

American actress and singer Jennifer Lopez and Sean 'P Diddy' Combs in carVinnie Zuffante, Getty Images

17. His Love Life Got Messy

After dating and living together several years, Combs and Porter broke up in 1999. If you did the math correctly, you’ll realize that Combs had something going on with Lopez long before that. When they made their relationship official, they became one of the biggest celebrity It couples.

But things looked much better from the outside than they actually were.

Sean 'Puffy' Combs and Jennifer Lopez at partyKevin.Mazur, Getty Images

18. He Drove Her Crazy

Lopez called her relationship with Combs a “crazy, heightened time”. Reportedly, she always suspected him of cheating on her. And honestly? That isn’t hard to believe. She’d get in her head about his lies and try to track him down to find out where he really was.

And if that wasn’t bad enough, they both got in trouble with the law.

Jennifer Lopez in beige top looking at the camera Christopher Polk, Getty Images

19. He Got Her In Trouble

Nothing about Combs and Lopez’s visit to a club in New York City in 1999 seemed out of the ordinary. That is, until Combs got into an argument with another man. The conflict turned physical, and someone who worked for him released some bullets.

Combs tried to get away with his new boo, but the authorities caught up with them.

Sean Combs   Jennifer Lopez at an eventStephane Cardinale, Getty Images

20. They Got Locked Up

Authorities took them both in when they discovered a weapon in Combs’ vehicle. Ultimately, courts released them both and cleared Combs of any charges. But by 2001, Lopez couldn’t take it anymore, and the two ended their relationship.

Perhaps the whole “bad boy” thing went to his head, because he just couldn’t stay out of trouble.

Jennifer Lopez at eventTom Hevezi , Getty Images

21. He Was Unhinged

The scene at the club wasn’t the first physical alteration to get Combs into a bad spot. Earlier that same year, he got into it with a music manager from Interscope Records, Steve Stoute. All things considered, his behavior isn’t all that surprising.

However—all things considered—his supposed reason for getting physical with Stout is extremely surprising.Sean 'Puffy' Combs performing on stage in whiteFrank Micelotta Archive, Getty Images

22. He Had His Limits

Combs got into fights and cheated on his girlfriends, but even he drew the line at blasphemy. He recorded a music video with Nas for their song “Hate Me Now” that showed both of them crucified. Afterward, Combs thought it disrespected the Christian faith, and requested the scene be removed.

When it debuted, he found they had ignored his wishes—and he lost it.

 Rappers  Jay-Z (L) and Sean Scott Gries, Getty Images

23. He Went Ballistic

In a rage, Combs stormed down to Stoute’s office and attacked him. He injured the manager, and ended up being charged for his behavior. None of his charges seemed to stick, though—not to his conscience, anyway. Whether or not he really cared is uncertain, considering he kept getting into situations.

American rapper and producer Puff Daddy in black suitNeil Munns, Getty Images

24. They Caught Him (Again)

In the early 2000s, authorities picked Combs up again. This time, at least, his wrongdoings seemed more benign. They charged him with driving without a license. He paid his dues, and started focusing more on his music ventures. In his romantic life, things seemed to be turning around as well. Or, maybe, they were actually doubling back…

Hip-Hop artist Sean 'Puffy' Combs performingScott Gries, Getty Images

25. He Got His Girl Back

After an alleged short relationship with international supermodel Naomi Campbell, Combs restarted his relationship with Kim Porter in 2003. By his own account, he’d always loved her, even when he cheated on her and dated other women.

It could have been a bit of a hood love story, but it didn’t take long for things to go south.

Kim Porter and Sean Johnny Nunez, Getty Images

26. He Did It Again

Combs and Porter dated for another few years, and found out they were expecting twins together. It should have been a happy time, but just a few months before the birth, Porter received terrible news—for her, anyway. Tucked away in another state, Sarah Chapman gave birth to a baby—allegedly Combs’ baby. A hood love story indeed.

Rapper Sean DOUG KANTER, Getty Images

27. He Made A Scene

The situation already looked bad, but Combs complicated things further by insisting Chapman take a paternity test. When the results came back, they confirmed she’d birthed his baby. Combs committed to caring for the child (his third biological child at this point), but his relationship with Porter didn’t survive the drama.

P. Diddy onstage performing at the United We Stand: What More Can I Give?Scott Gries, Getty Images

28. She Gave Up On Him

Porter stayed with Combs until she actually had their twin girls, but she broke up with him shortly after. I can’t blame her—cheating on a pregnant woman really takes the disloyalty up a few notches.

According to multiple reports, Combs is actually a good dad to all his children—but his behavior in several other areas left much to be desired.

Sean Michael Caulfield Archive, Getty Images

29. He Couldn’t Choose

Back in 1994, Combs used the name “Puffy” for his first music credits. This transitioned into “Puff Daddy” in 1996, then to “P. Diddy” in 2001. There doesn’t seem to be any substantial explanation for these name changes, other than Combs’s preferences.

But when he decided to change his name again in 2005, it didn’t go as smoothly as before.

Actor-rapper Sean 'P Diddy' Combs attends the ceremony honoring him with a star on the Hollywood Walk of Fame on May 2, 2008Joe Seer, Shutterstock

30. He Took It

Combs made the declaration on a morning show—he wanted to be called “Diddy”. It didn’t come as the hugest news to his US-based fans. But over in the UK, DJ Richard Dearlove sued him over the use of the name—a name Dearlove had been using for years.

Combs settled the case, and can’t use that name in the UK. That was the least of his problems.

p. diddy in whiteudo salters photography, Shutterstock

31. They Came For Him

Back in the late 90s, Roger Mills interviewed Combs for his television show. Things went as planned until Mills touched on the subject of the Notorious B.I.G.’s untimely passing. When he asked Combs about his alleged involvement, the rapper totally flipped.

He angrily ended the interview, refusing to continue. Why the anger, you ask?

Sean David Klein, Getty Images

32. He Looked Guilty

As mentioned earlier, B.I.G. worked closely with Combs on his label for many years. With the feud between B.I.G. and Tupac ending with both of their deaths, Combs’s involvement soon came into question. Some reports allege Comb’s connections gave him the power to put a hit out on the West Coast rapper. But did he actually do it?

Sean P. Diddy Combs walks by carJames Devaney, Getty Images

33. He Got Away

While the case came back to haunt him in the 2000s, Combs remained technically clear of any involvement in either Tupac or Biggie’s deaths. Perhaps his anger in the interview with Mills came from the pain of the loss. But what happened after the interview is definitely suspicious.

Sean “Diddy” Combs exiting the Crosby Street HotelAspects and Angles, Shutterstock

34. He Tried To Cover It Up

Combs’s team tried to buy the recording of the interview. When Mills refused, they allegedly followed him to his car and tried to force him to give it over. Ultimately Mills sued Combs and his team for the incident. But, you guessed it, courts cleared Combs of any charges or involvement.

He had a tight team—but all didn’t go smoothly on the inside.

Sean P. Diddy Combs performs at Lifebeat's UrbanAID 2,Frank Micelotta Archive, Getty Images

35. He Made Drama

As the head of his own label, Combs seemed to take as many liberties as he wanted with the control of his artists. One artist, Mase, thought he did too much. In 2006, Mase wanted to leave the label to join the hip hop group G-Unit, but Combs refused. This led to a diss track from an already successful rapper: 50 Cent. Things with the label started to tank.

Mase performs onstage at the KMEL JamAnthony Pidgeon, Getty Images

36. He Fell Off

Bad Boy Records’ success continued to dwindle as the 2000s progressed. They lost multiple artists, and mostly failed at their attempts to work with genres outside of Hip Hop. They attempted a partnership with the wildly successful Warner Music Group, but that fell through too. But music proved not to be all Combs was up to.

Bad Boy EntertainmentAmericasroof , CC BY-SA 3.0 , Wikimedia Commons

37. He Became A Brand

Combs figured out early in the game that he needed multiple ways to make money. He created his own fashion line, Sean John, and soon saw great financial success. It proved an excellent addition to his repertoire, even winning a national fashion award.

It didn’t come easy though—not for his foreign workers, at least.

Photo of P DIDDY performingAndrew Lepley, Getty Images

38. His Employees Struggled

In the 2010s, news of the horrendous working conditions in his Honduran factories came to light. Workers claimed they were not only underpaid, but also forced to work with limited bathroom access, random body searches, and more.

Combs claimed he didn’t know, and made hasty updates. This was just the start of Sean John’s problems, though.

Sean Alberto Tamargo, Getty Images

39. The Material Was Suspicious

Another unfortunate detail about his designs came out as well. Allegedly, the fur on some of his jackets came from raccoon dogs. On all fronts, that's just not a good look. Comb claimed no knowledge of this either, and pulled the “fur” jackets right away.

Despite the setbacks, he continued to see success with the brand and other business ventures, though his romantic life didn’t shape up at all.

an Shareif Ziyadat, Getty Images

40. He Had A Secret

Combs signed a young, up-and-coming R&B songstress to Bad Boy Records in 2007—Cassie Ventura. If you’re keeping track, he broke up with Kim Porter for the second time that same year. Rumors that the two got involved circulated for years, but the relationship didn’t hit the streets until 2012. Things looked promising this time…for about a minute.

Sean Combs and Cassie VenturaSky Cinema, Shutterstock

41. He Tried Again

Okay, so, they dated for a little more than a minute. Technically, they dated for about ten years—although I use the word “dated” quite loosely. The two broke up and reunited several times, which doesn’t surprise anyone (except maybe them?).

Some reports claim that Combs continued to be unfaithful—but even more problems arose.

Sean Diddy Combs and Cassie during 2006 MTV European Music Awards CopenhagenJeff Kravitz, Getty Images

42. He Didn’t Trust Her

Several reports made it seem like Ventura stepped out on Combs, too. Granted, with the on-again-off-again nature of the entire relationship, it’s hard to be certain. Combs must have suspected her though, considering one instance in which things got a bit too handsy between them—and not in a romantic way either.

Music Mogul and Designer Sean Shareif Ziyadat, Getty Images

43. They Got Physical

In 2016, authorities stepped in because of a particularly escalated disagreement. Reportedly, Combs asked to see Ventura’s phone. When she refused, he forcibly took it from her in a heated argument. Her mother called the authorities, and no serious charges came of the incident.

In the end, though, the lack of trust didn’t end the relationship. It was something else.Sean Shareif Ziyadat , Getty Images

44. He Wouldn’t Put A Ring On It

By Ventura’s account, she ultimately ended the relationship in 2018 because Combs refused to take things to the next level. She wanted a marriage, and he wouldn’t propose. Notably, once they ended things, she got married the very next year—to a personal trainer who worked for Combs. Messy. But maybe Combs likes messy.

Cassie Ventura (L) and Sean Chelsea Lauren, Getty Images

45. His Secrets Came Out

In 2017, shocking allegations about the music mogul came to light. His personal chef of several years, Cindy Rueda, filed a lawsuit against him with extremely serious claims of misconduduct and harassment. By this point, you probably aren’t surprised by his misbehavior at all.

But stay tuned, because the details get weird.

Sean 'Puffy' Combs in suit looking at cameraEverett Collection, Shutterstock

46. He Liked It Freaky

Rueda’s account of the way Combs insisted she do her job brought much into question. By her telling, Combs often made suggestive, inappropriate, and rude comments to her. But that wasn’t even the worst part. He often made her serve him and his guests either when they were engaged in intimate acts or completely in the buff. Yeah, not the best “work” environment.

Pioneering producer, rapper and pop phenomenon Sean 'P Diddy' CombsAnthony Harvey, Getty Images

47. He Paid Up

There doesn’t seem to be much information existing about an official response from Combs or his team to this allegation. He did, however, settle the case out of court, likely by paying a sizable sum. As always, the allegations went away, and Combs continued his work in multiple industries. Perhaps bad boys do finish first.

Sean Combs Has Lunch With Mom In New YorkSpencer Platt, Getty Images

48. He Got Game

Neither his numerous children from multiple women nor his track record of being a cheater seemed to do much to keep Combs out of the dating game. He’s gone on to date multiple celebrities, including Lori Harvey and Gina Huynh. His most recent bit of relationship drama, though, came from his involvement with another young female performer.

Recording artist Sean CombsLawrence Lucier, Getty Images

49. He Kept It Up

In 2022, Combs confirmed a relationship with rapper Caresha Brownlee, better known as Yung Miami. Granted, he claimed the nature of the relationship to still be very casual, and not at all exclusive. That’s a good call, considering the fact he had his seventh biological child, Love, at the end of the same year—with yet another woman.

yung miami looking at the cameraJamie Lamor Thompson, Shutterstock

50. He’s Got The Love (STILL)

Somehow, with all the questionable activity in his personal life, Combs still managed to see great success in multiple arenas and to maintain the affection of many fans. In 2021, he officially changed his middle name to “Love,” and used the virtue to inspire the title of his most recent album - “The Love Album: Off The Grid”.

: Sean ‘Diddy‘ Combs attends the 2023 Met Gala Celebrating Jeff Kravitz , Getty Images

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