15 Rappers Who Date Women Who Are WAY Out Of Their League

There are many world famous rappers that sell millions of albums and tour the world. However, even their incredible success and fame don’t completely explain how they’ve managed to date the most gorgeous women in the world. A majority of these rappers are average-looking and in some cases, below average. Looks aren’t everything, and there are many positive qualities that these rappers have. Regardless, it’s still a mystery what these women find so attractive about these men. Perhaps, some women like their money, status, and popularity or maybe they just like their personalities.

Rappers are known for having it all and rapping about it. They like fancy jewelry, lots of money, fast cars, and women. In fact, most hip-hop videos feature some of the hottest and most beautiful women in the world. So, it’s really no surprise that these talented artists go after babes that are totally out of their league. They have the money, fame, and confidence to bag a perfect 10. The true mystery is why these women would chase these men. Of course, there are a plethora of male rappers that are handsome and hot. They do pretty well for themselves but they still don’t land some of the women on this list. There is a famous saying that states, “Beauty is in the eye of the beholder.” This list is clear proof of that. Here is a look at 15 Rappers Who Date Women Who Are Way Out of Their League.


15 Diddy

Before Alex Rodriguez, before Marc Anthony, and even before Ben Affleck, there was Diddy. When Diddy was still Puff Daddy, he managed to date the utterly beautiful Jennifer Lopez. Diddy is the founder of the world-famous Bad Boy Entertainment. Additionally, he has released several memorable albums, such as No Way Out, The Saga Continues, and Last Train to Paris. In 1999, Diddy and JLo had the entire world buzzing with their relationship. It was quite shocking since JLo’s a perfect 10 and Diddy is…well...Diddy. In December of 1999, they were arrested in connection with a shooting outside of a New York club. They were a regular Bonnie and Clyde. JLo was later exonerated, but Diddy had to go to trail. He was found not guilty of all charges but in the end, he really lost. JLo and Diddy broke up not too long after the trial.

14 Waka Flocka


Waka Flocka took his name from Fozzie Bear’s catchphrase, “waka, waka.” Waka gives hope to all Muppets fan that they too can proudly represent the show and somehow still date way out of their league. Waka has released two albums, which are Flockaveli and Triple F Life: Friends, Fans and Family. Tammy Rivera is best known for her role in the reality series Love & Hip Hop: Atlanta. She has also released her own swimwear and the single “All These Kisses.” Waka and Tammy have had a very rollercoaster-like relationship. They married in 2014 but eventually separated because of Waka’s alleged cheating. He was clearly heartbroken and realized that he could never do better. It appears that as of 2017, they are in fact back together. Unlike most men, Waka realizes that he totally lucked out and did whatever it took to get her back.

13 Ice-T

Legendary rapper Ice-T gives hope to all the aspiring rappers out there that they too can marry a model way out of their league. At one point, Ice-T was best known for the controversial track “Cop Killa,” but nowadays is best know for marrying the gorgeous Coco Austin. Coco is a model, dancer, and reality TV personality. She worked several Playboy mansion parties and events early in her career. In 2008, she was featured in Playboy magazine showing off her “assets.” Coco could probably date any rapper, celebrity, or millionaire she’d like. In 2002, Ice-T and Coco married and have been together since. They even renewed their vows for their 10th anniversary. Additionally, their love for each other resulted in a popular reality series, Ice Loves Coco. The series ran for 3 seasons from June of 2011 to January of 2013. Later, they briefly hosted their own talk show, Ice & Coco.

12 Bow Wow

Bow Wow started his career at the young age of 13. The best part of starting his career so young is that he also started dating before his voice changed. Bow Wow has dated women that not even the most beautiful male celebs could ever dream of. He released his first album in 2000 and became quite the child star. When he was 17 and on the rise, he dated another 17-year-old on the rise, Ciara. They met on the set of the intro video for his concerts. They dated for roughly two years before the relationship came to an end. While dating, Bow Wow admits he wasn’t smart enough to have a serious relationship with her. She went on the have a very successful career and never looked back. He continued to date women totally out of his league. Bow Wow entered into a relationship with model and reality show personality Erica Mena. It ended when he decided to get back with his child’s mother.

11 French Montana

French Montana is quickly becoming a dominant force in the world of hip-hop. However, he’s also becoming a dominant force in the world of dating. He’s still somewhat early in his career, so his dating list will likely expand as his music catalogue does. After his divorce, he was involved with two very beautiful women that are totally out of his league. French was living with fellow rapper Trina but they were never an official couple. Although Trina noted that she was pretty much his girlfriend. She was shocked to find out that French was seeing Khloe Kardashian at the same time. Eventually, Trina and French ended their relationship once she found out. French and Khloe only dated briefly and were never too serious. Khloe just finalized her divorce from Lamar Odom and felt she jumped too quickly into a relationship with French. Recently, rumors swirled that French was dating actress Sanaa Lathan after being spotted together.

10 Wiz Khalifa

It’s every teenage boy's dream to date a hot supermodel and Wiz Khalifa makes his dreams come true. Wiz Khalifa had his big breakthrough with the number one single “Black and Yellow.” He’s released several popular albums, including Rolling Papers, Blacc Hollywood, and Khalifa. However, he is best known for once being married to the stunning Amber Rose. Model Amber Rose was featured in several videos for well-known artists, such as Nicki Minaj, Ludacris, and Young Jeezy. She briefly hosted her own talk show, The Amber Rose Show, and currently hosts the podcast Loveline. Khalifa was able to do the impossible by going out of his league to marry Rose. Rose and Khalifa started dating in 2011 and were married by 2013. In 2014, they broke up and divorced, which seemed to be tough on both. Khalifa will likely fulfill every teenage boy's second dream, which is to date several more supermodels.

9 ASAP Rocky

In 2011, ASAP Rocky had his big breakthrough with his critically acclaimed mixtape, Live. Love. A$AP. As a child, he likely dreamed of the day he’d be a billionaire surrounded by a million women. He’s probably even surprised with some of the women he’s dated. With his success, he’s dated women that he likely never thought he’d get close to. In 2011, he started dating fellow rapper and all-around hottie Iggy Azalea. They were so in love that Iggy had his breakthrough album tattooed on her fingers. In 2012, he revealed that they were no longer together. He then began dating the utterly gorgeous model Chanel Iman, who is best known for being a Victoria’s Secret Angel. They dated for several months before breaking up. Recently, he’s been linked to Kendall Jenner. One can only assume that ASAP Rocky will continue to have a great career. Also, one can only assume that he’ll continue dating women way out of his league.


8 Notorious BIG

Notorious BIG is considered one of the greatest rappers of all time. The King of New York dated a plethora of insanely beautiful women but the one at the top of the list is R&B singer Faith Evans. Despite being one of the greatest MC’s, Faith was still out of his league. That is more a testament to how gorgeous Faith is because clearly, Biggie had game. Biggie and Faith were both singed to Bad Boy Records and met at a photoshoot. They soon started dating and got married on August 4, 1994. Faith found herself dragged into the feud between Biggie and Tupac. In fact, Tupac claimed to have a relationship with Faith on the infamous diss track “Hit ‘Em Up.” Prior to Biggie’s March 1997 murder, Faith and Biggie had separated. At the time, there was speculation that Biggie had cheated on Faith with rapper Lil Kim. Later, Faith recorded the tribute song “I’ll be Missing You,” dedicated to the late rapper. 

7 Meek Mill

Meek Mill went from selling mixtapes to signing with Rick Ross’ label. He’s one of the best known up-and-coming rappers. He’s had number one singles and launched his own record label. He released his debut album, Dreams and Nightmares, in 2012. However, his greatest accomplishment was dating fellow rapper Nicki Minaj. She has quickly become one of the biggest rappers in the world. She’s known for her unique and eccentric fashion sense, as well as her fearless rhyming. She’s broken Billboard records and tours the world. Meek Mill shocked the world when he started dating Minaj, who many feel is way out of his league. Meek and Minaj started dating in 2015 and had everyone talking. The relationship lasted for roughly two years before Minaj ended it with Meek. In 2017, Minaj released the single “Regret in Your Tears,” which chronicles her relationship with Meek.

6 Future

Future is on top of the hip-hop world. He is likely the future of hip-hop. He’s released several chart-topping singles, such as “Where Ya At,” “Low Life,” and “Mask Off.” His success resulted in him dating women that he could only dream of as a teenager. Before his success, he would have known of the goddess that is Ciara. She’s had a great career and is considered one of the most beautiful R&B singers. In 2013, Future and Ciara became engaged, which was a shock because...well…she’s Ciara and he’s Future. They have one child together born in May of 2014. However, the engagement was called off after Ciara discovered that he was cheating on her, which is even more shocking because who in their right mind would cheat on Ciara? The breakup was not smooth and resulted in Ciara suing Future for defamation.

5 Jermaine Dupri

At the 2003 MTV Video Music Awards, host Chris Rock said, “And I’ve been lovin’ Janet Jackson my whole life…if I could just get near her, if I could just talk to her, if I could just touch her. Then I see Jermaine Dupri walk in the room and I’m like, damn, I had a shot! We all had a shot!” Jermaine Dupri has worked with some of the biggest names in the music industry, including Usher, Mariah Carey, and Jay-Z. However, he shocked the world when he started dating pop icon Janet Jackson. They started dating in 2002 but attempted to keep the relationship out of the public eye. They dated for roughly 7 years and eventually broke up in 2009. Janet is one of the best-selling artists and widely regarded as one of the hottest celebs. Not only is Janet out of his league, but they’re not even in the same universe.

4 Big Sean

Big Sean isn’t a bad-looking dude and is actually a pretty good dresser. He’s very talented and has made a lot of money. Regardless, it still doesn’t totally explain some of the beautiful women he’s dated. Sean is best known for the albums Finally Famous, Dark Sky Paradise, and I Decided. In 2013, Sean began dating actress Naya Rivera, with whom he became engaged later that year. Naya is best known for portraying Santana Lopez in Glee. In 2013, she also released her first solo single, “Sorry,” which featured Big Sean. However, they broke up in 2014. Later that year, he started dating another superstar on the rise, Ariana Grande. Grande is quickly becoming a pop sensation in her own right. Sean and Grande recorded several tracks together, including “Right There,” “Best Mistake,” and “Research,” They dated for roughly 8 months before breaking up in 2015. He is currently dating hottie Jhene Aiko. Both collaborated on an album together and formed the duo Twenty88.

3 Travis Scott

Rihanna is widely considered the most beautiful celebrity alive. She’s also considered a “cool chick” that just about every guy wants to be with. She’s had quite the dating life and has been linked to Chris Brown and Drake. Travis Scott started his career around 2009, and by that point, Rihanna was already an international phenomenon. In 2015, Scott had the whole world dancing with his hit single “Antidote.” 2015 was quite the year for Travis Scott and in the midst of his success, he dated Rihanna. To say that Rihanna is out of his league is an understatement. She’s in a league all her own but Scott managed to penetrate it. The relationship was short-lived and ended quickly. Rihanna has her own impressive dating list but Scott is just starting is out. Scott continues to add to list by currently dating Kylie Jenner.

2 Lil Wayne

Lil Wayne has broken records, sold out stadiums, and won a Grammy Award. However, his greatest accomplishment is dating women that are so out of his league they’re in a completely different sport. Lil Wayne first met actress Lauren London in the late ‘90s. They eventually started dating but the relationship ended in 2009. Later in 2009, she gave birth to their son. In the same year, Wayne had another child with singer Nivea. Wayne and Lauren remain friends since splitting up. In 2014, Wayne made headlines after being spotted with the insanely gorgeous Christian Milian at the ESPY Awards. They soon revealed that they were in fact dating. They worked together in various ways, including on music, tours, and videos. However, the relationship ended at the end of 2015. One can only assume that Wayne is busy making new music and dating women not even he thought he could land.

1 Jay-Z

Throughout Jay-Z’s whole life, he’s always been proving people wrong. He likely didn’t doubt for a second that he could land the most gorgeous woman on earth. Jay-Z has won 21 Grammys, started his own Entertainment Company & sports agency, has his own clothing line, and is considered one of the greatest rappers of all time. However, his greatest achievement in life is convincing Beyoncé to date and then marry him. Beyoncé has won 22 Grammys and is one of the most beautiful musicians. They started dating around 2003 but kept a very low profile as a couple. They married in 2008 and now have a daughter and twins. They’ve often appeared in each other’s music and performed together on occasions. They’re widely regarded as the most popular, influential, and richest couple. They have a combined net worth of roughly $1.15 billion.

Sources: VH1

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