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.
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.
Dooley 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.
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.
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.
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.
lev 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.
Fourandsixty, 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.
Al 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.
Al Pereira, Getty Images
Sign up to our newsletter.
History’s most fascinating stories and darkest secrets, delivered to your inbox daily. Making distraction rewarding since 2017.
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.
Nitro, 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.
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.
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.
Columbia 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.
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.
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.
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.
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.
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.
Stephane 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.
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.
Frank 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.
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.
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…
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.
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.
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.
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.
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.
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.
udo 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?
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?
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.
Aspects 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.
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.
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.
Americasroof , 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.
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.
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.
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.
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.
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.
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.
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.
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.
Everett 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.
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.
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.
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.
Jamie 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”.
