The best team to arguably ever play in the NBA was the 1995-96 Chicago Bulls. They had everything on that team: good shooters, rebounding down low, incredible defense, the list goes on and on. Of course it helps when you have two future Hall of Fame players that helped lead the charge. When you have Michael Jordan and Dennis Rodman on your team, you have a clear advantage from tip-off.

Everybody knows who Michael Jordan is. A six time champion, six time NBA Finals MVP, five time regular season MVP, and countless other awards; Jordan is viewed by many as the greatest to ever play the game of basketball. He led the Bulls to a dynasty, winning six championships in a span of eight years. He could have probably won another one or even two if he hadn’t taken a two year hiatus to pursue his dream of being a professional baseball player after his father was murdered. Jordan was great, but he couldn’t have done it without Dennis Rodman.

Rodman was known as one of the most outrageous characters in the NBA. He helped the “Bad Boy” Detroit Pistons win back to back championships in 1989 and 1990. Then, he found a second life in Chicago helping Jordan win three more in 1996, 1997, and 1998. He was known for his uncanny rebound ability and tough defensive play along with being a mad man with on and off the court antics.

Both of them had their talent on the court. But they also had their fair share of hot girlfriends and even a marriage or two along the way. There are some big names associated with these two athletes, rightfully so as they were winning championships and having fun along the way. This list looks at who these two men dated, so you can decide who had more game. Without further adieu, let’s take a look at some pictures of past hookups of Michael Jordan and Dennis Rodman.

20. Jordan: Vanessa Williams

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Jordan knew how to shoot his shot and most of the time make it as well. That was no different with the first girl we give to you that he had a thing with. She has made appearances in everything from “The Love Boat”, to “Ugly Betty”, to “The Adventures of Elmo in Grouchland”. You name it, she probably did it. The woman we are talking about is Vanessa Williams.

Williams is an actress, signer, and fashion designer who we have seen around for years. The two were rumored to have a little fling for a bit while Jordan was helping the Bulls become a perennial powerhouse. Obviously they didn’t end up together and it took them a few tries to find the love of their lives, but it is a nice story to say the least. Williams always had a pretty face and nice body which was made for television. Her and Jordan together was nice for a while, but it just didn’t feel like it was going to last forever. But, we can enjoy the story as Williams kicks it off for one of Jordan’s best hookups.

19. Rodman: Madonna

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Dennis Rodman is a mad man. This seems to just be conclusive and known when talking about his career. Sure, he won a few Defensive Player of the Year awards and was known as one of the best rebounders in the history of the game, but it didn’t come without wild actions along the way. The dying of his hair, the kicking of a camera man, the repeated outbursts at referees; Rodman clearly didn’t have a filter. Rodman’s dating life was crazy too as he went after the older and much more wild Madonna.

Madonna once has the title as the “Queen of Pop”. She also made appearances in movies such as “Evita”, and “A League of Their Own”. She also had hit songs such as “Everybody” and “Burning Up” make its way up the Billboard charts into the top five for big club hits. Madonna was very multi-talented and had a very successful career as a singer and actress. She decided to have some fun with Rodman when he was still in the NBA. They obviously didn’t end up together either, but it is interesting to think that these two had a thing.

18. Jordan: Karla Knafel

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This next fling Jordan had involves all of the great elements for a juicy love story. A story where there was money involved to keep the relationship quiet, DNA tests, and a lot of drama that in the grand scheme of things, wouldn’t matter two decades later. Jordan has certainly learned his lesson since, but doesn’t mean we can’t resurface the story and woman to life.

Karla Knafel was an adult actress who knew how to have her fair share of fun. She starred in many films and that must have tickled Jordan’s fancy as they indulged in a secret love affair. Supposedly, Jordan gave Knafel $250,000 just to keep her mouth shut about what was going on between the two of them. Imagine getting that much money to keep a big secret like that? It’s not a bad chunk of change to spend on whatever she wanted to at the time. But, good for Jordan for indulging into a fun little time with Knafel.

17. Rodman: Vivica A. Fox

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Rodman has been known for his zaniness and interesting fashion choice. The same happened in 1997 when he went to the Oscars. He rocked an all blue suit along with a top hat that made people talk about him. Rodman always knew how to get people to keep talking about him whether it was for a big rebound or big act. He did have some fun with actress Vivica A. Fox though.

Fox is an actress and television host that continues to act today. She had some big roles in films such as “Two Can Play That Game”, “Juwanna Mann”, and “Booty Call”. She dazzled on the screen and made headlines when it came out her and Rodman were dating. At the 1997 Oscars, she wore a sparkling dress that looked great on her. It was a fun thing to talk about, but probably for the best that they went their separate ways. But good for Rodman for shooting his shot and making it with Fox. Your move, Michael.

16. Jordan: Juanita Vanoy

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Sometimes in the professional sports world, women are only known because they are married to the professional athlete. That was the case with Michael’s next hookup. A lot of people eventually leave the single life and settle with someone they can spend the rest of their life with. Michael Jordan was no different, even when he was winning championships galore with the Bulls. He eventually settled down with his first wife, Juanita Vanoy.

Vanoy was Jordan’s wife for more than a decade. They had two sons and a daughter together and seemed like they would be together forever. That was not the case as they divorced for good in 2006, with Vanoy getting a divorce settlement supposedly of $168 million. Vanoy was a supportive wife though for Michael through all of the good and bad times. As the picture shows, she was supportive and there when Jordan needed her the most.

15. Rodman: Carmen Electra

via gotcelebrity.com

This next hookup and eventual wife of Dennis Rodman’s is just straight up sexy. She knows how to give everyone a show and knows how to make everyone pay attention to her on screen. She ended up dating and eventually marrying Rodman which people were hoping would last. However, it didn’t and they both moved on. They were a nice story being together though for a while.

Carmen Electra was a dancer and now actress. She appeared in many paraody films such as “Disaster Movie”, “Date Movie”, “Meet the Spartans”, and “Scary Movie”. She sure has come a long way from being an adult film actress. The two were married in November of 1998 and divorced just five months shortly after in April of 1999. The two were together for only a short period of time, but they did look really good together and this could have been a fairy tale ending if they worked things out. But they didn’t, and all we are left with are memories like this one of the two happy to be in each other’s company. This is a good counteraction by Rodman, let’s see if Michael can find a way to one up his old teammate.

14. Jordan: Kylie Ireland

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Jordan and Rodman definitely have one thing in common: they both love to have some fun with adult actresses. Jordan seemed to enjoy it so much that he couldn’t help but get with these types of women before he eventually settled down. Michael continues to shoot his shot and make it with this adult film actress. She certainly is no Carmen Electra, but she is a nice consolation prize if any for Jordan.

Kylie Ireland was an adult actress that claimed she had fun with Jordan just like other women have said. Ireland definitely has some edge to her, you can tell by the red hair and tattoo on her right arm. Michael was such a dominant figure in the game of basketball that maybe he just needed somebody that could keep up with his lifestyle. Ireland looks like she could definitely put Michael in his place if he stepped “out of bounds”. She knows what it takes to make in that adult film industry and Michael knew what it took to make it in the NBA. Put them together and you got this girl dating a sports icon. Although it didn’t last, what a ride that was for Michael. Dennis, can you deliver the next bombshell?

13. Rodman: Jaimyse Haft

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This next woman of Rodman’s past definitely understands the pain of going through multiple breakups and heartache just like Dennis did throughout his life. People have to remember Dennis had a rough childhood growing up with no father in the house and a mother that apparently never told Dennis she loved him. In short, Dennis didn’t know how to love. But he sure did try and he ended up dating this actress short term.

Jaimyse Taft is an actress that has appeared in films such as, “House of Usher”, “Tony 5”, and “Lords of the Underworld”. She definitely has the looks to attract a man like Rodman. Nice legs, beautiful body, nice smile, and long flowing hair can help attract any man, let alone Dennis Rodman. The fling was short lived as both moved on to the next chapter of their lives. You have to wonder if maybe Taft could have helped Rodman get a few more acting and television roles. You never know, but it would have been fun to see. Still, Taft is a sight to see and a good shot made by Dennis. What do you have to say about that one Michael?

12. Jordan and Karla Knafel

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Nobody ever said repeats were out of the question or against the rules here. If they have more than one photo, then why not show them, right? We mentioned before how Jordan had his little randevu with Karla Knafel. She looked in the first photo like she was ready to shoot a scene in the classroom where the teacher comes on to the student. Jordan must have been into that to have his fun with her.

Here, the younger Jordan and Knafel are arm in arm and taking a seemingly innocent picture on a bed. It seems harmless enough, right? Only those two know what really went on. For all we know, they could have had some fun before this photo was taken and went viral for everyone to see. Knafel definitely had her fair share of fun in front of the camera, so who is to say she didn’t do the same with Jordan? Her blonde hair and shiny smile shows off her soft side and another side Michael probably liked about her. Plus, the all white jumpsuit on Jordan was a nice touch as well. Another good job done by number 23.

11. Rodman: Madonna

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One thing about couples who are a little bit crazy; they seem to just fit together. Like peanut butter and jelly or Oreo’s and milk, Dennis Rodman and Madonna just seemed to fit together. They were both successful in their respective professions and both were looking for someone to have fun with.

They may have been crazy, but at least for a short period of time they were crazy for each other. Dennis had his fun but they have both moved on. Ironically enough, Rodman wasn’t the only Bull that Madonna dated in the 90s as she infamously had a fling with Scottie Pippen and Jordan flirted with her, only to be rejected. Needless to say, MJ probably wasn’t used to that.

10. Jordan and Yvette Prito

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Sometimes, you just have to go through a few relationships and hookups before you find the woman/man of your dreams. Michael Jordan definitely had his fair share of fun as a player for the Chicago Bulls during their dynasty run. Now, he is settled down, an NBA owner, and somebody who wants to live the rest of his life with a good woman by his side. He found that in Yvette Prieto.

Prieto is a Cuban American model who looks good by Jordan’s side. As you can see from the photo, she has a bright smile that can make M.J. smile at a moment’s notice. The most sincere and sweet part about their marriage is Jordan proposed to Prieto on Christmas day. That was probably the best Christmas gift either of them could ever have imagined. His one time hook-up, now wife, is definitely somebody that we can get used to seeing. How are you going to come back from this one, Dennis? Can you even compete with somebody with looks of Prieto?

9. Rodman: Michelle Moyer

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Unfortunately for Rodman, he never found a girl to tie the knot with and live in holy matrimony with forever. He had his few marriages which didn’t seem to workout. But he also had his hookups that we have to give him credit for. He has done well for himself, but this girl just adds to the list of good hookups he has had. One of the hookups turned marriages Rodman had that was as short lived as his time with Dallas and San Antonio was Michelle Moyer.

Moyer was a girl that was married to Rodman for about a year before calling it quits. She had two kids with him, one son and one daughter. They married in 2003 and then quickly divorced in 2004. It really is a shame they didn’t work out together because she has quite the look going for her. She has nice legs that show in this photo, with a tight body and nice tattoo on her left arm. Her blonde hair is a nice touch to put the icing on top of the cake. Rodman may not have lasted life with her, but he certainly had a good time with her that will last in his memories. The pressure is now back on Michael to show us what he is made of.

8. Jordan: Kylie Ireland

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The pressure is on for Michael just like it was in every Finals her appeared in. He needs to make a serious move to go back on top of Rodman in this hookup battle. We said repeats are not off of the table, so we might as well bring back Kylie Ireland. Ireland we said was an adult film actress with a lot of history regarding her and Jordan having fun. But with this picture, it seems like Jordan may be pulling very much ahead of Rodman and never looking back.

Ireland knows how to look good in front of the camera like we have mentioned before and she is not afraid to show it. Jordan may be happy with his current wife Yvette Prieto, but that doesn’t mean he can’t reminisce about the times he had with Ireland when he has some free time on his hands without Prieto present.

7. Rodman: Vivica A. Fox

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We took a look at Rodman and Fox’s relationship previously. Fox was said to have had a little thing with Rodman, but could she have been the one that got away that could have made him the happiest man alive? That question unfortunately will never be answered. But for now, the answer to is Vivica A. Fox still hot is yes. Yes she is. The only question is what Fox saw in Rodman all those years ago.

She may not have had the best ending with Dennis, but she definitely can boost up his self-esteem and help make a good case for him in this against Jordan. There are three pictures left for each guy and the pressure is on. Will one of them be victorious?

6. Jordan: Juanita Vanoy

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Like we said, Michael Jordan is happily married to his new wife and is settling into a consistency between his work life and family life. Sure, Jordan has a ton of kids; but he seems to be handling it better now as opposed to in the past. While we commend Michael and hope the best for his new marriage, we have to look back and think about the good photos he took with his first wife, Juanita. Juanita gave Michael two sons and over a decade of her life to him and things still didn’t work out. At least we have a few pictures, including this one to remember her by.

Jordan and Vanoy look very good together. She is soft on the eyes and has a warm, inviting smile like a mother would. It seems like they just belonged together and were going to grow old together. But, that’s life sometimes.

5. Rodman and Michelle Moyer

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We always saw the rough and tough side of Dennis Rodman. He had to go up against some of the leagues best big men such as Patrick Ewing and Charles Barkley just to name a few. He always had to be mentally and physically tougher than his opponent to win, just like anybody else would try to do in sports. But there was a soft side apparently to Rodman as he was dealing with issues with his ex-wife Michelle Moyer. Moyer may have aged, but she still looks pretty good.

Her hair flows down smoothly, her lips and teeth show a lot of potential in a good woman, and she is by his side. There isn’t much more you can ask for if you’re Dennis Rodman. When the couple was having troubles, apparently they were doing everything they could to reconcile and clear their differences. That is an evident sign that Rodman truly cared for Moyer even though others might disagree. He is a big name throughout basketball, but even he could not escape human emotion for somebody else.

4. Jordan: Loredana Jolie

via thesun.co.uk

Of all the hookups and failed marriages and successful marriages we have seen of the two former Chicago Bulls players, we haven’t seen any sign of Playboy models. Well, that will change right now as we have one right here for all to see. It should come as no surprise that Jordan was the one who landed a fun time with this beautiful woman. Her name is Loredana Jolie and she knows a thing or two about athletes.

Jolie is a Playboy model with a history of having fun with professional athletes. She was reported to have a fling with former golf great Tiger Woods.She also reportedly had fun with Jordan as well for a brief period of time. Honestly, just look at her; she is quite the vision for sure. She clearly has a thing for professional athletes and will only date the top ones such as Woods or Jordan.

3. Rodman and Vivica A. Fox

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The old saying goes, “if it isn’t broken, then don’t fix it.” Well, if she continues to help Dennis’s case, he shouldn’t have to fix his approach. Rodman always had his reputation of living the wild life. We can only imagine what his life behind closed doors was like with Fox if she is coming out with photos like these.

If you weren’t a fan of Vivica A. Fox before, you probably are one now or should become one very soon. She definitely has some edge to her if she hooked up with a guy like Rodman. She knows how to have her fun but also be professional when the cameras roll around too which is a great sign.

2. Jordan: Yvette Prito

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Jordan’s final shot comes in the form of his new wife, Yvette Prieto. I feel as though it is just the right thing to do to put his new flame for his number one photo of his past hookups and such.

She has the same smile we talked about earlier that is making us smile and M.J. smile every chance he gets to see it. Her breasts are showing off nicely under her shirt. Finally. she is just showing pure joy and happiness taking a photo with the great one in the NBA known as Michael Jordan. Michael had his fair share of great hookups in the past, but don’t think Dennis won’t end this without a final knockout punch. Dennis, the floor is yours for the last time in this list.

1. Rodman and Carmen Electra

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Finally, we have come down to Dennis Rodman’s last picture of a former hookup/former wife. It comes none other than in the form of Carmen Electra. Like we said before, Electra and Rodman were briefly married; six months to be exact. But with a picture like this coming in at number one for Rodman, we can see why he went after her and tried to wife her up for the long haul.

Electra is just drop dead gorgeous. He had some crazy hookups in the past, but this one was a no doubt slam dunk by the former great rebounding forward. He was part of the “Bad Boy” Pistons teams in the late 1980s, and he just needed a “bad girl” to go along with him.

The call is still tough to make between these two player’s collection of hookup talent. You be the judge!

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