In 1989, Sean “Puffy” Combs left the brick sidewalks cemented throughout Howard University’s campus and found himself interning for Andre Harrell, founder of the now defunct Uptown Records. While working under Harrell’s leadership, Combs was introduced to the legendary Notorious B.I.G., but after getting let go from the former founder’s bombing record label, a young Puff Daddy took Christopher “Biggie Smalls” Wallace with him as he started his own label, Bad Boy Entertainment (now Bad Boy Records). From that moment forward, Puffy knew he was going straight to the top.
Although the man with a million nicknames was infatuated with his success and that of his artists, he soon became hypnotized with importance of family after he and his former girlfriend, Misa Hylton-Brim, brought Combs’ first child, Justin, into the world. From that moment forward, Diddy (as people later called him) wasn’t just enthralled with building an empire he was determined to create an unforgettable legacy, which he’s done with the help of his former and current girlfriends, Kim Porter and Cassie, respectively, his five biological children and his stepson and the many entertainers he’s helped rise to the top including Danity Kane, Day 26, Red Café, MGK and more. But while the smoke and mirrors that make the music industry may seem to be Puff’s No. 1 priority, there’s no doubt that his family comes first.
From his eldest son, Justin, who’s now playing football at UCLA to his twin daughters posing for magazine covers alongside their mother, Sean Combs has plenty to be thankful for. When it comes to Puffy and his family, just press play!
The Famous Photo
The pairing of famed rappers, Craig Mack and the Notorious B.I.G., was curated by none other than Sean “Puffy” Combs. In 1994, B.I.G. made his mainstream debut on Mack’s chart-topping single, “Flava in Ya Ear (Remix).” The two were signed under Puff’s Bad Boy Records (formerly Bad Boy Entertainment).
Rising to the Top
Diddy signed B.I.G. to Uptown Records in the early ’90s only to find himself let go from the label soon after. He figured if he wasn’t going to be working alongside Uptown Records founder, Andre Harrell, then he would work for himself and be better than the man who inspired him. Just after signing the man properly known as Christopher Wallace, Combs landed the NY MC a spot on the Who’s the Man? soundtrack in 1993 with Biggie’s now classic hit, “Party and Bulls***.”
Over the course of the next year, Puffy and the Notorious B.I.G. spent countless hours in the studio and had everything to show for it on August 4, 1994 when Wallace released his debut album, Ready to Die. While it is nothing but cliché, the rest is history.
All About the Benjamins
While Sean Combs will never be forgotten as the intern from Uptown Records, he started his fast track to fame in 1992. So fast-forward 20-plus years, and the man with endless industry nicknames sits as one of the biggest music moguls in history. He may not be the people’s champ, but he’s certainly about his business.
All He Needed
In a time when money, jewelry, women and liquor seemingly meant everything to the music world, it was still possible to find yourself lonely at the top. In 1995, Puff began dating his longtime girlfriend, model and actress Kim Porter. The couple’s relationship went on for 12 years and produced three children, Christian (1998), D’Lila Star and Jessie James (2006).
Over the years, Kim Porter has graced her fair share of magazine pages. In 1998, Porter posed alongside Combs for the cover of NOTORIOUS Magazine with the headline reading, “Puff, Daddy To Be.” Since then, she’s been seen in JET, Essence and now RUNWAY. This past March, the Georgia-bred model was named RUNWAY Magazine’s Spring 2013 cover girl, and boy does she know how to work a camera.
Men of the House
They may only be half-brothers, or stepbrothers in Quincy’s case, Al B. Sure’s son, but the biological separation that lives between Quincy Brown (22), Justin Combs (20) and Christian Combs (15) is an invisible divider. And there’s no question that their father has real love for each of them.
Stuntin’ Like His Daddy
Since stepping onto the music scene, Puff’s always been known for throwing a great party! So when it came to Justin’s 16th birthday, there was no shortage of out-of-the-box celebration tactics. Not only was the music heir’s coming-of-age party featured on MTV’s former extravagant display of extremely spoiled teenagers, My Super Sweet 16, he had a star-studded guest list that could compete with any of Jay-Z’s exclusive shindigs.
On December 21, 2006, Sean Combs and Kim Porter welcomed their youngest children, twins D’Lila Star and Jessie James into the world. The couple decided to name the girls in honor of their mothers. The Combs twins made their public debut in People Magazine in an article titled “Itty Bitty Diddys.” Since then, the girls were singing toddlers and tiaras long before the TLC show was created.
D’Lila and Jessie have seen the pages of Juicy, JET, Us Magazine and more, and walked more red carpets than some celebrities. And now, on the brink of their seventh birthday, there’s no telling what Hollywood may have in store for Daddy’s little girls, but the public is guaranteed to see it all.
Modeling With Mom
D’Lila and Jessie quickly followed in the footsteps of their mother as soon as their toddlerhood set in. They may have barely been able to walk, but posing for the camera was nothing less than second nature.
In 2007, Sean Combs took legal responsibility for his Chance, his daughter with longtime mistress, Sarah Chapman. After learning about Puffy’s affair, Kim vowed to never let Chance meet her twin daughters as long as she was breathing but somewhere along the line she had a change of heart.
Sharing many of the same genes as her sisters, Chance also finds herself modeling—in her case, for local department stores.
While Quincy Brown is Puff’s pseudo stepson, he’s always loved him as his own—helping take care of him since beginning his relationship with Kim in the mid-90s. As the couple’s romantic association came to an end shortly after their twins were born, Combs continued to act as a father to Quincy. Knowing he was raised from a music mold, Al B. Sure!, he found his place in entertainment and introduced himself to the world as International Quincy. Singing his way into the hearts of girls everywhere with singles like “Stay a While” and “The First Thing.”
Cassie Ventura and Sean Combs were a rumored couple for many years. Chatter filled the media rumor mill as fans, journalists and bloggers alike speculated about Cassie’s possible relationship with the Bad Boy Records CEO. From red carpets to birthday parties, the two have been spotted together around the world, but until last year they never commented on their status or feelings for one another. But that all changed when the two turned to Twitter to confess their love.
In late September of last year, the New York-bred mogul logged in under his Twitter handle, @iamdiddy, and posted a picture of the exotic model and said, “I’m a very lucky man #knowthat.” The 26-year-old beauty responded to the public display of affection by logging onto Instagram and posting a picture of her million-dollar-boyfriend on a jetski with a text that read, “love.him.”
While the Filipino-Mexican-African-American model/actress continues to grow her career as an entertainer, both on screen and on stage, she is absolutely loving the man standing beside her through it all.