The 20 Hottest Women Sean "Diddy" Combs Has Been With

Sean Combs, better known as P. Diddy or even just Diddy is well known for his massive influence and success in the music world. He started as a rapper and actor but is now more involved with producing records and being an entrepreneur. He owns Bad Boy Records which has been around since 1993 and developed many of the biggest music artists from the past couple decades. He is also the owner of his own clothing lines, Sean Jean and Sean by Sean Combs. This man has been a success in many ways and Forbes confirms it by listing him as being worth over $735 million.

With fame and success comes lots of power, influence and, well, relationships. Diddy has made quite a name for himself in the business world, but he has also made a name for himself in the world of females where it seems he can get any woman he wants. His love of beautiful women, especially models, has been well documented by paparazzi and multiple women coming forward with tell-all accounts of their relations with the music mogul. It is safe to assume you are curious to see what beautiful faces are included in this star-studded line up of ladies, so we have narrowed down his alleged conquests to a list of the top 20 hottest women Diddy has been with.

20. Alicia Douvall

Diddy sure did love him some supermodels, and he was infamous for flying them around and keeping them close to him. One of the many was the beautiful Alicia Duvall who he was rumored to have dated around 2002. Douvall is originally from Britain and known for being a model and also her involvement, in reality, TV shows. She is also well known for a number of plastic surgeries she has undergone. She claimed to be pregnant with Diddy’s baby but he denied it, and she sadly ended up miscarrying the baby, so the claim was never able to be substantiated.

19. Lil’ Kim

Kimberly Denise Jones or better known as Lil’ Kim is one of the most iconic female rappers in the music world. She has worn a lot of hats throughout her career, such as model, actress, producer, writer, and rapper. Kim is originally from New York and got her big start rapping with The Notorious B.I.G. as well as singing her involvement in the song “Lady Marmalade” for the film Moulin Rouge. She performed with Diddy and put out multiple hit songs with him. Around 1997/ 1998, the time he was with his girlfriend, Kim Porter, he was rumored to be having an affair with Lil’Kim, but it has not been proven.

18. Nicki Minaj

Although this one is seen as a long stretch by many who follow Diddy and his various diddies, Nicki Minaj is still a prime suspect for having more than just a friendly relationship with the music mogul. Minaj is mainly known for her mad musical and theatrical skills that have made her one of the most popular rap artists out today. She is actually the only woman to be put on the Forbes list of Hip-Hop Cash Kings. She is known to be dating Meek Mill, but there have been rumors in the past of her and Diddy since they work very closely on many projects and have been spotted out n’ about holding hands.

17. Misa Hylton-Brim

Miss Misa Hylton-Brim was Diddy’s high school sweetheart and the original claim to Diddy’s as a baby daddy. She is the mother of his oldest child, Justin, who was born back in 1993. Brim is a celebrity stylist and fashion designer who has recently dished on her relationship with him and his other baby mommas. She claims to get along with both of the other mothers, Kim, and Sarah, who he cheated on her with. She exposed the fact that he met both women around the same time and was sleeping with both while he was still with her. She claims to be somewhat of a peacemaker between the two and that she is still on good terms with Diddy.

16. Kim Porter

The infamous Kim Porter is famous merely because of her long-standing on-again-off-again relationship with Sean P. Diddy Combs. She was with him from around 1994 through 2007, and they have four kids together- one of which is technically not his son. Diddy adopted her first born son Quincy like his own, but Quincy is the son of the producer and singer Al B. Sure. They have had a tumultuous relationship over the years full of drama and infidelity, but they have stayed cordial and often friendly through it all. The main reason for their final breakup was his inability to stay faithful.

15. Keyshia Cole

The talented and beautiful Miss Keyshia Cole is best known for her business savvy as a producer, singer, songwriter and TV personality. This lady with her amazing set of lungs got the attention of many since her career took flight after working with MC Hammer and Tupac Shakur when she was only in middle school and high school. She has been the recipient of many music awards and has had a documentary and multiple reality shows about her life. She and Diddy put out a hit song together and rumors circulated especially after Gucci Mane rapped about her getting with Diddy while dating Young Jeezy. The rumors are not confirmed per usual.

14. Karrine Steffans

Karrine Steffens is widely known for her series of books, Vixen, that are a tell-all style series of life as an actress and video vixen for hip hop and rap artists. She got her start as an exotic dancer before she started starring in music videos with R. Kelly, Mystikal, and LL Cool J. She was also rumored to have been with multiple famous names such as Lil Wayne. In one of her tell-all books, she states that she got with Diddy after he broke up with J. Lo and while she was dating someone else. However, she claims that her then boo, Irv Gotti allowed her to sleep with Diddy. She is also known for outing him in her book as “average” in bed.

13. Aubrey O’Day

One of the most famous performers in Diddy’s own pet singing group, Aubrey O’Day has had her fair share of tabloid drama and rumors about her involvement with Diddy. O’Day is a singer, songwriter and TV personality that made her way up through the ranks through musicals and Broadway as well as singing in a band called Dumb Blonde before she came on the reality show Making the Band starring P. Diddy. She was the first member accepted to the band and her fame took off from there. She appeared in Playboy, Maxim and other such magazines. Diddy ended up firing her from the band for her “overly sexed image” and her not being the same girl he originally signed. Other sources state that he was controlling and jealous and cut her for personal reasons.

12. Cameron Diaz

This famous smoky eyed blonde bombshell was yet another of Diddy’s rumored conquests. Cameron Diaz is best known for her movie roles in many of the top box office action movies and romantic comedies. She also started out as a fashion model and is now a producer. Diaz was named one of the highest paid actresses in Hollywood in 2013, and her movies are still going strong with them making an average of 7 billion worldwide. The two never admitted to being an item or anything more than friends but their frequent partying and disappearing together turned into a whole lot of rumors that we actually believe.

11. Diana Bianchi

This lovely little trouble maker was famous for making the news for ascandalous reason that would shape the rest of her life. She slept with a married man, and it ended up going to trial since he was found guilty for manipulating her and paying her to keep quiet. She ended up on good terms with his wife but had many issues such emotional issues after the fact. Soon after all of the drama had subsided, the aspiring singer was known to have been seeing and messing around with Diddy while he was still with the mother of his children, Kim Porter.

10. Tracey Edmonds

Although this particular relationship was more rumor than anything, it is certainly not farfetched that Tracey Edmonds and P. Diddy were hanging out on a more personal level. Edmonds is a well known successful businesswoman, TV personality, and model. She is mainly known for her business prowess and ability lead and direct successful entertainment operations. She was married to both Babyface and Eddie Murphy, but neither relationship worked out. Later she met Diddy and a tabloid quoted her saying that she was whisked off her feet by him and that he was the man for her. She later stated that the quotes were made up.

9. Emma Heming Willis

The lovely Malta-born British model and actress Emma Hemming, now Emma Heming-Willis is mostly known for being the wife of action film star Bruce Willis. She was famous for her appearances in magazines and as a runway model for big names such as Valentino, Ralph Lauren, Victoria’s Secret, Christian Dior and much more. Before she married Willis, she modeled for Diddy in a risqué photo magazine spread. We aren’t sure when exactly they dated, but it was a bit after 2001 when People magazine was referring to her as his girlfriend soon after his breakup with J. Lo.

8. Sarah Chapman

Diddy’s relationship with Sarah Chapman has been a source of media frenzy and plenty of drama over the years since he was involved with her at the same time he was involved with his main lady Kim Porter. At one point Chapman was pregnant with her second child with Diddy at the same time that Porter was pregnant with twins while with him. Diddy tried to deny that it was his child, but a DNA proved him wrong and clearly got him in big trouble. She has since come forth with a tell-all interview that claims she was never trying to step on Porters’ toes and that she and Diddy are just friends.

7. Sienna Miller

Sienna Miller is a model, actress and fashion designer of American and British nationality. She is famous for many of her big screen roles and also for her relationship and failed engagement to Jude Law. She and Law split up because of his highly publicized relationship with the nanny of their children. Soon after their separation, she was spotted hanging out and partying with none other than Sean Diddy Combs. The paparazzi loved catching them out and loved it, even more, when they found them out for breakfast the morning after. Diddy ended his relationship with his infamous ex soon after this was publicized.

6. Penelope Cruz

The famously stunning and sexy model and actress Penelope Cruz is rumored to have had relations with Diddy in the summer of 2007. She is known for her many strongleads and supporting roles in top movies. She is also known for her charity work and volunteering in Uganda, India, and Nepal. The two had been known to be close friends since about 2005, but the rumors didn’t start until later. At the time, she was supposedly being fought over by Diddy and his buddy Pharrell but Diddy seemed to have the upper hand since he had her ride with him to a Prince concert and the two were seen getting pretty cozy that night.

5. Ingrid Vandebosch

This gorgeous model and actress are now mainly famous for being the wife of the champion NASCAR race car driver, Jeff Gordon. Ingrid Vandebosch is from the Netherlands but has been all over the world from Paris to New York working for big names such as Christian Dior, Elle, Vogue, Glamour, and Marie Claire. She also appeared in Sports Illustrated in 2008 and was the face of the popular makeup brand Artistry. She was also known for her blow up at a fashion show where Diddy had her seated next to his infamous ex Kim Porter – apparently she was not impressed with his sneaky seating arrangements.

4. Natassia Malthe

Natassia Malthe is one of the many models that made Diddy swoon and with good reason. This stunning babe originated from Norway and is also of Malaysian descent- quite a striking combo. She was a successful and celebrated model, actress and ballet dancer in Norway. Diddy definitely put her on everyone’s radars when he started flying her all over the place and paying all her travel and accommodation expenses. In 2008, he flew her out as usual and had her sit front and center at his Sean John runway show. Although the rumors are not confirmed or denied, we know this bad boy probably got what he wanted.

3. Jennifer Lopez

One of Diddy’s most famous relationships was with the one and only Jenny from the block. They were basicallycelebrity royalty during their time together and definitely considered a power couple. They were together around 1999 – 2001 and had a pretty good go at it. Unfortunately, when they were together when he was involved in a shootout, and they both admit that the legal proceedings following the situation put a serious strain on their relationship. Although he was acquitted from any wrong doing in the case in 2001, they broke up soon after. This may have been the cause or the fact that his ex-was still in the picture may have contributed as well.

2. Naomi Campbell

Diddy dated the famously gorgeous supermodel Naomi Campbell briefly in 2002. Naomi is most famous for being one of the coveted Victoria’s Secret Angels for years. She is also known for her beautiful light eyes that make her look very exotic. Campbell is originally from Britain and made her way to the top 3 models in the 80s through modeling, acting and singing. She is also known for the many lawsuits filed against her for assaulting her personal assistants and workers. The relationship between her and Diddy did not last very long at all, but apparently it ended cordially since they remain friends to this day.

1. Cassie

This stunning songstress has been the object of many man’s affections for obvious reasons- she’s asbeautiful as she is talented. She and Diddy have avoided talk of their relationship and denied it for pretty much as long as the rumors started circulating back in 2007. However, she came on the scene heavy when he broke up with his longtime on-and-off girlfriend, Kim Porter, and she has been a pretty permanent fixture ever since. They have tweeted some pretty revealing pictures about their life that seem to go against all their claims of just being friends, so we think they are definitely together on some level.