Things You Never Knew About Diddy

Carly Silver
Updated April 22, 2024 20 items

Sean "Diddy" Combs, man of many names and many more dollars, occupies a place in pop culture few others can match. Plenty of cool Diddy stories exist which exemplify his incredible, over-the-top career and lifestyle, and a few of them happenedĀ before he hit it big. In fact, his first moniker, Puff Daddy, actually stems from a childhood nickname. Apparently even before fame, Diddy already thought quite highly himself. Throughout all of SeanĀ Combs'sĀ name changes, he held his title as a record label exec.Ā Fun facts about Diddy include his monumental influence on music of the '90s and 2000s.Ā More than a music mogul, Diddy holds stakes inĀ liquor,Ā fashion, restaurants, and television. As a result, Diddy now stands as one of the wealthiest rappers-turned-CEOs.

With all these accolades and riches, naturally a couple of dark DiddyĀ facts also exist, including the infamous Bad Boy Curse people say follows the label. Regardless of how you view him, one cannot deny the influence of Diddy not just on music but on American pop culture in general. When you're Diddy-big, the stories just follow you.

  • Diddy's Father Died In A Drug Deal Gone Bad, A Fact His Mother Kept From Him

     

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    Single mom Janice Combs raised her kids, Sean and Keisha, after her husband, Melvin, died. Until he became an adult, Sean believed his father had passed away in a car accident. While receiving an honorary doctorate at his alma mater, Howard University, Combs revealed in a speech to the audience what his mother never told him:

    "My mother always told me that he died in a car accident. But something about that it just didnā€™t feel right . . . So, as soon as I got here I went to the library and I did some research. I used the microfilm at Founders [Library] to search through all the newspapers. And when I typed in my fatherā€™s name and the day he died, I read in the Amsterdam News that he had been murdered in a drug deal gone bad. Right there in that library I realized thereā€™s nothing greater than a motherā€™s love and desire to protect her child.ā€

    Frank Lucas, on whom filmmakers based American Gangster, was also business partners and pals with Melvin Combs.

  • He Loves 'Happy Socks' With 'Fun Designs' On Them

     

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    Diddy cares very much about aesthetics, right down to his footwear. Diddy's personal shopper, Derek Roche, says his client tests his "limits and boundaries" as a stylist. With his shopper at his side, Diddy purchases everything from authentic Scottish kilts in Glasgow to elaborate designer gowns for girlfriend Cassie. Perhaps his most bizarre aesthetic interest is his love of socks, specifically ones with fun designs.

    Roche told New York Post:

    Mr. Combs loves his "happy socks" ā€” fun designs from Paul Smith or Rob Kardashian. We labeled them ā€˜happy socksā€™ because they just make him feel good ā€” it could be polka dots, it could be stripes or lightning bolts.

  • A Detective Alleges He Organized Tupac's Murder And Thereby Responsible For Biggie's

     

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    With the death of Christopher "Notorious B.I.G." Wallace in 1997, Diddy lost both his best friend and Bad Boy's flagship artist. Yet according to ex-LAPD officer Greg Kading, responsibility for the deaths of both Biggie and arch-rival Tupac Shakur trace back to Diddy's door. Kading, who spent three years investigating both cases, alleges Diddy paid members of the Crips gang $1 million to kill Tupac in 1996. As a result of Tupac's death, Suge Knight, head of Shakur's record label, Death Row, allegedly retaliated by ordering a hit on Biggie the following year. These theories act as the premise for USA's crime drama, Unsolved: The Murders Of Tupac And The Notorious B.I.G..

  • Though He Never Graduated, He Received An Honorary Doctorate From Howard University

    Though He Never Graduated, He Received An Honorary Doctorate From Howard University

    Diddy attended Howard University for two years, eventually dropping out to pursue an internship at Uptown Records with music exec Andre Harrell. Though he left the institution, it clearly remained a part of his character. The multi-hyphenate mogul spoke at Howard's 2014 commencement ceremony amid protests from some over the fact he never finished. At the ceremony, Combs received an honorary doctorate from his alma mater. Moved, he said, "Howard University didnā€™t just change my life ā€“ it entered my soul, my heart, my being and my spirit." 

  • Diddy Helped Pioneer The Blending Of Hip-Hop And R&B In Records

     

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    Diddy deserves recognition as a pioneer of the hip-hop and R&B sound that blossomed in the early '90s and continues to see success today. When he got the chance to stand in at a session after an R&B producer no-showed, Combs took his hip-hop sensibilties to the board and created a smash hit. Influenced by Brucie B. and Kid Capri's mixtapes, Diddy started with remixes such as "Come and Talk to Me," and eventually made the sound mainstream through collaborations with TLC, Faith Evans, and the Queen of Hip-Hop Soul, Mary J. Blige.

  • Diddy Made Assistants Hold Umbrellas For Him (But It Pays Off)

    Diddy's assistants work for their salary. In 2003, a picture of then-employee Fonzworth Bentley holding an umbrella for Diddy in Saint-Tropez became super-popular. Unsurprisingly, the fashion mogul has a personal shopper acquires him any garment he wants.

    But Diddy's assistants don't stay assistants forever - one is now a US diplomat. Former assistant Dia Simms now acts as the president of Combs Enterprises. Tiesha LeShore also started out working for Diddy, now works as a production coordinator at REVOLT TV. Bentley, not one to be left in the shadow of his past, even penned a New York Times-bestselling etiquette guide.

  • At A Celeb Basketball Game He Promoted, A Stampede Killed Nine People

    In 1991, Combs worked as a promoter, along with rapper Heavy D, for a charity basketball game played by prominent hip-hop artists. Located at City College, the event attracted far more people than the venue could accomodate. As a result, the 3,000 attendees created a stampede. Twenty-nine people were injured, and nine died. The cause of the stampede was deemed to be inadequate security. And several lingering lawsuits stuck with Diddy in later years.

  • Bad Boy Records Reportedly Takes Terrible Care Of Its Artists

    Bad Boy Records Reportedly Takes Terrible Care Of Its Artists

    Plenty of artists found great success through Bad Boy Records, but quite a few regret signing onto Diddy's label. When he found himself facing prison time, rapper Black Rob claimed Diddy and Bad Boy "left [him] for dead." In a more chilling example of his ruthlessness, former Bad Boy signees 112 claim the mogul once left them stranded in a blizzard.

    Rap trio The LOX skyrocketed to fame on Bad Boy, but when the group wanted out, he said no. The group went on a press campaign called "Free the LOX," printing T-shirts for fans and publicly pleading with their label boss on radio. Another of Diddy's signees, rapper Mase, actually confronted Diddy on-air with a set of release papers, which the mogul surprisingly signed. For all the public successes Bad Boy has seen, it's also seen its fair share of public controversies.

  • He Changes Names So Many Times That Sometimes He's Forced To Backtrack Them

     

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    Sean Combs changes his stage name as frequently as Xtina changes genres. Known as "Puffy" as a kid, he went by "Puff Daddy" as a label head and artist in the 1990s. By 2005, he reemerged as "P. Diddy," eventually shortening it to just "Diddy." But he still goes by P. Diddy in the UK because a British artist already used "Diddy" as a name - and got a whole bunch of cash from the American Diddy in a settlement.

    In 2008, Diddy decided to (temporarily) go by Sean John, also the name of his clothing line. That never caught on; the same went for his 2011 moniker, "Swag." After a shift back to Puff Daddy in 2014, Diddy later stated he wanted to go by "Love" or "Brother Love" in 2017; when it didn't land, he told fans he was only kidding.

  • Diddy Treats Other Celebrities, Even The Biggest Ones, Any Way He Sees Fit

     

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    Some celebrities are big, but Diddy is just bigger, and he knows it. Selena Gomez recalls a time when Diddy handed her his valet ticket: "Because he thought I was the valet lady.ā€

    Though now a big fan of Kendrick Lamar, Combs tried on a few occasions to beef with hip-hop's boy wonder in 2013. When West Coast-based Kendrick called himself the "King of New York" on a Big Sean song, Diddy responded with an Instagram meme dismissing his claim. When they ran into each other at Diddy's Amaretto launch party, an inebriated Combs attempted to pour a drink on Lamar, only for J. Cole to step and prevent an incident.

  • His Former Personal Chef Sued Him For Sexual Harassment

     

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    In 2017,Combs's ex-personal chef, Cindy Rueda, filed a sexual harassment lawsuit against him, claiming he forced her to serve him meals while he engaged others in intercourse. She said Combs walked around naked in front of her and asked if she liked his nude body.

    After she complained to the relevant parties at Combs Enterprises, Rueda said she was fired after being lured into a situation where her employer framed her for theft. A judge ruled she must pursue private arbitration, rather than a public court case, for her suit. Combs claimed her suit was a shakedown for money.

  • Diddy Was Arrested For Weapons Violations At A Club Shooting With Then-Girlfriend Jennifer Lopez

     

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    In 1999, Combs took to Club New York, with Bad Boy artist Shyne and Combs's then-girlfriend, Jennifer Lopez in tow. After Combs reportedly disrespected another patron, shots rang out at the club, wounding three people in attendance that night. Lopez and Combs fled the scene only to get arrested, with Combs allegedly bribing a driver to claim ownership of a gun. In the end, Shyne went to prison for nine years, angrily saying Diddy sold him out. Combs was acquitted, although he dealt with civil suits until 2011, and the major fallout from the event caused him to change his name to P. Diddy.

  • He Pled Guilty to Assaulting A Record Exec With A Chair And Champagne Bottle

     

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    In 1999, Combs assaulted record executive Steve Stoute. Why? Stoute managed artist Nas, with whom Combs collaborated with on the song "Hate Me Now." For the "Hate Me Now" video, Combs filmed a scene with him crucified like Christ, but then wanted it cut. The final video still contained the controversial scene, however, and Combs confronted Stoute, striking him with a bottle of champagne, a phone, and a chair. Combs pled down to a reduced charge and only had to do one day of anger management.

  • A Doctor Told Him He 'Goes Too Hard'

     

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    Although Diddy is almost 50, he still parties hard. However, his lavish lifestyle is starting to catch up with him. In a 2018 GQ article, Diddy said his doctor told him he "goes too hard." Knowing Combs, though, that likely hasn't slowed him down too much. 

  • He Constructs Elaborate Party Invitations For His Amazing SoirĆ©es

    He Constructs Elaborate Party Invitations For His Amazing SoirƩes

    Combs hosts lavish parties, from his annual White Party to New Year's bashes. His ingenuity extends to his party invitations. On The Tonight Show with Jimmy Fallon, the host revealed Combs sent self-destructing party invites! Fallon needed to write down the address of the festivities before the note self-destructed.

    Of his party passion, Diddy told Fallon:

    ā€œI love being a host. Itā€™s about hosting and itā€™s about giving ā€“ nobody is going to remember the takers, Jimmy. Nobodyā€™s going to remember the takers, theyā€™re going to remember the giversā€¦"

  • While Pregnant With Twins, His Ex Discovered He Fathered A Baby With Another Woman

     

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    A public life as ostentatious as Diddy's likely creates some tension in his personal life. He adores his six kids - son Justin, with stylist Misa Hylton-Brim; son Christian, twin daughters D'Lila and Jesse, and adoptive son Quincy, with model Kim Porter; and daughter Chance, with fashionista Sarah Chapman. But Diddy got into a bit of trouble with Porter when she was pregnant.

    In 2006, while carrying the couple's daughters, Porter discovered her boyfriend Combs, unbeknownst to her, had recently fathered another child - Chance. Porter approached Diddy after the twins' birth, and he finally admitted it; ā€œI would have preferred to find out from him because thatā€™s a man,ā€ Porter said at the time. After that, she left him.

    On Wendy Williams in 2017, Combs said he met Porter and Chapman around the same time and was "friends" with all of them. He claimed one of them broke his heart and the other consoled him, leading to the conception of all three girls. 

  • Did Diddy Steal Cassie From Her Ex?

     

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    Diddy and longtime girlfriend Cassie, also a Bad Boy artist, make a stylish pair on the red carpet. But the start of their relationship reportedly began in a much less polished fashion. In 2005, Cassie dated record exec Ryan Leslie, who introduced her to Diddy and got her signed to Bad Boy. Leslie produced her breakout hit, "Me & U," saying, "Cassie was my girl in New York City. We were going out romantically, and we made a song and put it out just for fun."

    Eventually, Cassie and Diddy connected more than just professionally, leaving Leslie by the wayside. This stung Leslie, and he still talks about Cassie today, albeit as a "product." His 2013 song "Black Mozart" at one point boasts, "My ex-chick is so hot Diddy wifed her": that same year, Leslie also said, "Itā€™s life man, people have to do what they wanna do to be happy.ā€

  • Entrepreneur Diddy Is A Pioneer In Music, Fashion, Spirits, And More

     

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    When he gets bored of being an artist, executive, or entrepreneur, Diddy simply dips  into any one of his other lucrative endeavors. In 2016, he sold the majority stake in his clothing line Sean John, which rakes in an astronomical $450 million annually. Sean John and his own personal style led him to be named 2004 CFDA Menswear Designer of the Year, becoming a pioneer in supporting people of color in fashion design.

    Through his promotion of vodka brand Ciroc, Diddy popularized the beverage as an alcoholic drink of choice for celebs. For fans who abstain, he launched a brand of fitness water called AQUAHydrate with Mark Wahlberg. For the silver screen, Diddy appears as a judge on singing competition The Four and masterminded the music network REVOLT TV. In 2018, Diddy reportedly held a net worth of $825 million.

  • Diddy Says He Confronted Suge Knight After That Infamous Source Awards Diss

    Diddy Says He Confronted Suge Knight After That Infamous Source Awards Diss

    The tension between West Coast-based Death Row Records, headed by Suge Knight, and East Coast-based Bad Boy Records, headed by Diddy, flared up at the 1995 Source Awards. Knight went up on stage and seemingly dissed Diddy, saying: "Any artist out there that wanna be an artist, and wanna stay a star, and wonā€™t have to worry about the executive producer trying to be all in the videos, all on the records, dancing ā€” come to Death Row!ā€

    Diddy later revealed that Knight's outburst surprised him. ā€œI really couldnā€™t believe it because homeboy, me and him were friends," claimed Combs. Later, Diddy confronted Knight about his comments. Knight supposedly responded that he wasn't talking about Combs, but about So So Def boss Jermaine Dupri. Dupri later dismissed that claim, saying, "Me having beef with Death Row? Never. Suge was in my office kicking it."

  • Diddy Donates To Many Important Causes

     

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    Besides his many business ventures, Diddy is an avid philanthropist. In 2003, he ran the New York City Marathon and raised $2 million for a children's charity. In 2011, he saved the Harlem Boys and Girls Club from going broke. In 2016, he donated $1 million to the School of Business at alma mater Howard University and pledged to donate clean water to the people of Flint, Michigan. In 2017, he gave $100,000 to Puerto Rico after the devastation of Hurricane Maria, a further $25,000 to victims of Hurricane Harvey in Texas, and $100,000 to Harry Belafonte's The Gathering for Justice, which raises awareness for numerous civil rights and social issues. In 2018, he gave $200,000 to a charity supporting healthcare for Ugandan mothers, inspired by his artist French Montana.