12 Of The Biggest 'Players' In Hollywood

For such a big place, Hollywood has fairly small quarters. It seems like everybody is dating everybody, and sometimes they have that one person on repeat; you know the one who can always go back to when they are done with the flavor of the month. Relationships in general are hard to navigate and even more hard to maintain; but when you live that celebrity lifestyle, it certainly makes it easier to run from that commitment (or does it?). There are plenty of excuses that can keep a famous man or woman single; the constant traveling for work, the pressure that goes into keeping a spouse happy when you have to maintain a career in the spot light and the lack of public validation (on the spouses side) in order to save that career. The player type in Hollywood does not have a distinct look, personality or even a particular taste in women. When you really think about it, the only reason why they seem like players is because one innocent date can be reported in tabloids and on blogs as a “torrid love affair” or a “whirlwind romance”. So to no fault of their own, they end up with the title of player. But hey, who are we to label them any different? Read on to see a list of 12 big Hollywood players.

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12 Lindsay Lohan


Chronic serial dater, one could say that this is another form of addiction for actress Lindsay Lohan. Publicly, Lohan has been linked to actors Aaron Carter and Wilmer Valderama, magician Criss Angel and musician, actor and hottie Jared Leto, but Ms. Lohan does not discriminate, she has also been with DJ Samantha Ronson and Yahoo heiress, Courtenay Semel. In addition to embracing her bisexuality, Lohan also likes to date from every working class. Who can blame her? Clearly she enjoys experimenting. Lohan may be more known for her dating escapades than her career at this point, but this hasn't slowed Lindsay down; she has shaped up a little bit and took herself across the pond; can’t wait to hear the dating stories to come.

11 Cameron Diaz


Blond, tall, funny equals hot, but Ms. Diaz just cannot seem to stay in one place (until recently). Chalk it up to bad luck, bad dating habits and everything in between, but Cameron seems to have the hardest time sticking to a long term relationship. Diaz has dated actors, musicians, producers and bankers, she has her hand in every pot and she looks great doing it. It looks like she has finally settled down for now though, with Good Charlotte guitarist/front man Benji Madden; but who can forget her trysts with Justin Timberlake, Gerard Butler, Vincent D’ Onofrio and Ed Norton.

10 Derek Jeter

Baseball player Derek Jeter isn't only a player on the field, he also knows how to kick game off the field. Serial dater and professional playboy, Jeter has had his pick of the litter, including singers like Mariah Carey and actresses like Jordana Brewster (from Fast and the Furious franchise), Gabrielle Union and Justin Timberlake’s baby mama, Jessica Biel. He goes through women as quickly as he goes through bases, and he isn't ashamed of it. Although most of the women he has run through are either now married or in committed relationships, Jeter finds himself always scoring a replacement hotter than the last.

9 Sienna Miller


All the way from across the pond, Sienna Miller has boys wrapped around her finger, even before she made her debut stateside. Torrid affairs with the likes of Matthew Rhys and Jude Law, only seemingly encouraged her behavior. Miller has gone on to bigger celebrity names including P. Diddy, and James Franco; but what makes her public affairs exciting is the fact that there seems to be no shame in her game. Her image exudes party girl and she has the lifestyle to back it up. Although, she recently got the opportunity to settle down with a younger man and popped out a baby girl. Let’s see what a baby daddy and a baby girl do to her game.

8 P. Diddy

This guy isn't afraid to spread the love, over and over and over again; musician, producer, mogul and all around hard worker, P. Diddy never goes in glass half empty; he does everything all the way or not at all. Same rules apply to his love life; he’s not just going to date you, he’s going to shower you with gifts, a baby (or two, or three), a sad break up and very public make up. The proof is in the pudding people, just ask habitual baby mama and only official girl Kim Porter, singer Casey, Jennifer Lopez and fellow list maker, Cameron Diaz.

7 Wilmer Valderrama


Who knew that Fez (That 70’s Show) would be the one who knew how to wine and dine the ladies? He has dated everyone from Disney stars to co-stars. Wilmer Valderrama has been linked to Lindsay Lohan, Minka Kelly, Ashlee Simpson (she wrote a song about him titled Boyfriend, look it up), Mandy Moore (who he has gone on record stating a less than satisfactory sex life), and repeat offender Demi Lovato, whom he is currently dating again. How can he get all of these hot women? It must be his confidence because he does not have a good track record with after break up interviews.

6 Rihanna

Singer Rihanna has made no secret of her love for boys. She has also made no secret of her love for serial dating. Although RiRi had a long standing relationship with fellow musician Chris Brown, she has seemingly moved on to bigger, better and safer endeavors, including Shia LaBeouf (before his unfortunate series of events), repeat offender and rapper Drake, football player Matt Kemp and actor, Josh Hartnett (Random!). Rihanna hasn't slowed down and considering she is in the prime of her life, who could blame her? There are so many options in the celebrity world, all ripe for the picking.

5 Lil’ Wayne

Rapper Lil’ Wayne makes his dating lifestyle no secret to the world; he is clearly an open book and isn't afraid to admit when he’s “wifing up”. Like Diddy, Wayne always seems to leave his girls with the gift of a child. To date, Wayne has four children with four women and shows no signs of slowing down. These women include actress Lauren London, singer Nivea, reality TV star Toya Carter (who gave him his first child at 15), and radio personality Sarah Vivan. Wayne also has had tryst with several video models like Dhea, Karrine Steffans and Candace Cabrera.

4 Taylor Swift

So young and so many partners; musician Taylor Swift gets around musically and publicly. It is believed that most of Taylor’s songs are based off of true experiences from her very public relationships. The two now go hand in hand. It is probably safe to say that if you date Taylor Swift, you should look out for a song with your name on it. She is a true player in the game of love and lust, and boasts several names under her belt, like actor’s Garret Hedlund, Taylor Lautner and Jake Gyllenhaal, to name a few. Musicians like John Mayer (repeat offender), Joe Jonas and Harry Styles. Taylor Does not discriminate though, she also has had her hand in the political pot with the likes of Conor Kennedy and Patrick Schwarzenegger. The list goes on and on, and includes men from all walks of life.

3 John Mayer

Typically referred to as the "quintessential douche bag", singer John Mayer gets around and he uses his guitar, shaggy tresses and soft voice to do so. His bad boy, rockstar image gives Mayer the ammunition he needs to be so confidently outrageous with his dating pattern; hooking up with everyone from Oscar nominated actresses, to Grammy award winning singers, Mayer has no problem showing the world who he is. He has been with celebrities like Jennifer Aniston, Jessica Simpson, fellow list makers, Taylor Swift and Minka Kelly, Vanessa Carlton and Jennifer Love Hewitt (who appeared in his Your body Is A Wonderland video). However of course, when he needs a new hit track, he goes back to Katy Perry and they make beautiful music together.

2 Leo Dicaprio


Known for only dating supermodels, Martin Scorsese’s golden boy Leonardo DiCaprio, is usually photographed with a bevy of models surrounding him on a private island. It is a guarantee that he is at least dating one of those women and will acknowledge her publicly when the time is right. DiCaprio has run through Gisele Bundchen, Bar Rafaeli, Naomi Campbell, Kidada Jones and Erin Heatherton. That is just the bare minimum of a list that includes a few actresses and musicians. The upside to dating Leo is you will definitely get recognized when you guys are together, and even when you break up.

1 Michelle Rodriguez


Actress Michelle Rodriguez takes our number one spot, simply because she has no fear in her dating rituals. With a long list that includes both men and women, Rodriguez has been linked to both Zac Efron and Cara Delevingne, in the last 6 months (her turnaround time is fast) and other high profile celebrities that include Lenny Kravitz, Vin Diesel and Colin Farrell. Rodriguez has gone on record stating that she just isn't good in long term relationships and admitted that 6 months is about the longest she can spend tied down to someone. Looks like she’s just a free bird.

Sources: pagesix.com

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