Celebrity Serial Lotharios
The little black books of these celebrity men read like a who's who of Hollywood, but a new generation of serial daters have surfaced. So is it the old or new class of Hollywood hotties that take the mantle for A-list ladies men?
PA PhotosLeonardo DiCaprio
First up are the Old Timers; and leading the pack is the inimitable Leonardo DiCaprio. This real-life Romeo sent many-a-teenage heart a-flutter in the 90s and sealed his sex symbol status as ill-fated Jack Dawson in Titanic. However, the course of true love has rarely run smooth for this Hollywood hottie...
Rex FeaturesNaomi Campbell
Although we all hoped that Kate Winslet was his one and only, it transpired that Leo's heart went on only for supermodels, which in 1995 meant none other than Naomi Campbell.
PA PhotosLeonardo Dicaprio and Gisele
Gisele
Indeed, DiCaprio's love for the catwalk's finest never waned and in the early part of the Noughties, he dated Brazilian megamodel Gisele...
Getty ImagesBar Rafaeli
...But, short of hitting an iceberg, Gisele and Leo hit the rocks in 2004 and in 2005, he stepped out with Israeli model Bar Rafaeli...
Wenn[/b]Blake Lively[/b]
...However, after six years together and upteen unsubstantiated rumours of marriage, the pair called it quits in 2011. Meanwhile, Leo has since been snapped on a loveboat (well, yacht in Cannes) with Gossip Girl Blake Lively.
PA PhotosMatthew McConaughey
Although Matthew McConaughey is now a bonafide family man, back in the day this Texan-born bongo player was making sweet music with more than a few of Tinseltown’s most eligible bachelorettes...
Getty ImagesAshley Judd
...After hitting the big time in legal drama A Time To Kill, Matthew briefly dated his onscreen wife Ashley Judd in 1996...
Rex FeaturesSandra Bullock
However, it transpired that McConaughey only had eyes for his other A Time To Kill co-star, Sandra Bullock. Despite splitting in 1998 after two years together, McConaughey famously said in 2001 that he believed that the two still might rekindle their romance one day, saying: “I wouldn't rule it out. I wouldn't, you know.”
Rex FeaturesPenelope Cruz
However, by 2004 Matthew had captured the imagination of his Sahara co-star Penelope Cruz, shortly after she had split from a pre-sofa-jumping Tom Cruise...
Getty ImagesJanet Jackson
Yet by early 2006 this Transatlantic couple had called it quits and according to reports the sexy Southern gent had hooked up with, um, Janet Jackson...
PA PhotosCamila Alves
But it was to be model Camilla Alves who finally tamed McConaughey. After meeting in 2007, the couple soon got serious and now have two children together.
PA PhotosJustin Timberlake
Indeed, it's not just Matt McConaughey that has caught the eye of Janet Jackson over the years... Step up Justin Timberlake. Once a bleach-haired boyband member of *NSync, JT successfully transitioned to Sex God solo artist - somewhere round about 2003 - and has since become the toast of Hollywood. However, whether a singer or actor or even MySpace entrepeneur, JT has never been short of female attention...
PA PhotosBritney Spears
JT's first high-profile girlfriend was none other than Britney Spears. At the height of her fame, they were the golden couple of teens across the globe; whether working double denim together, or extolling their Disney virtues, we just couldn't get enough of them...
PA PhotosJanet Jackson
But amidst rumours of infidelity and a rather intriguing music video with a Britney look-a-like, pop's golden couple parted ways in 2002 and rumours were soon rife that JT was dating his Superbowl “wardrobe malfunction” partner Janet Jackson in 2004...
PA PhotosCameron Diaz
...However, despite nipple-gate it wasn't to be and Justin soon found love with the gorgeous Cameron Diaz...
PA PhotosJessica Biel
Yet after three years together, the pair split in 2007 and ol' Trousersnake mended his broken heart with Jessica Biel. However, after months of speculation, the two split four years later in March 2011 although smoothy JT has since said Jessica is one of “the most important people in my life”...
PA PhotosMila Kunis
But, the first rule of Hollywood dating is that you can never keep a lothario down, so it came as little surprise when the Sexy Back singer was romantically linked to his Friends With Benefits co-star Mila Kunis over the last couple of months... Especially with photos like these!
WennColin Farrell
Everyone loves a bad boy and Irish totty Colin Farrell has long fitted the bill. With his dulcet Irish lilt women the world over - not to mention a few of Tinseltown’s A-list - fell for the Gaelic charms of this former Ballykissangel actor turned Hollywood box office star.
PA PhotosBritney Spears
When Britney wanted to shed her wholesome girl-next-door image, who did she turn to? None other than Dublin native Colin Farrell. When the two turned up unexpectedly to a premiere together in 2003, they were already guaranteed the column inches, but lo, when they locked lips right on the red carpet – que pandemonium. Colin’s smooch with good girl Brit secured his bad boy status, while it swore in a new era for Britney.
Rex FeaturesLindsay Lohan
And just a year later, playboy Colin was at it again with another teen queen, this time Lindsay Lohan. It was a meeting of minds when these two Hollywood hellraisers were said to have gotten close in New York in the summer of 2004...
PA Photos
PA PhotosAngelina Jolie
...Until, that is, he was reportedly dating his other Alexander co-star Angelina Jolie. Although as we well know now, 2005’s real Angelina Jolie love triangle was more scandalous than we could have ever dared imagine...
PA PhotosBrad Pitt
And so we come to the last of the old guard and the object of most of the female world’s affections - for well-over twenty years now - Brad Pitt. Probably the Hollywood hotty, Brad has had more A-list dates than you’ve had hot dinners.
Rex FeaturesSinitta
Even when he was a struggling actor and before he hit the big time, Brad could still charm the celeb ladies and in the mid-Eighties dated Simon Cowell’s ex Sinitta for two years...
PA PhotosJuliette Lewis
After the success of his brief appearance in Thelma & Louise, the job offers began to flood in and he started dating his Kalifornia co-star Juliette Lewis – who was 16 and 10 years Brad’s junior! – in 1992. Although his career went from strength to strength, Juliette’s has not quite managed to replicate the same success and in an interview in 2007, Lewis apparently bemoaned the size of Brad’s, umm, you know what... Bitter, much?!
PA PhotosGwyneth Paltrow
However, it wasn’t until 1994 that Brad was really on the map as a bonafide heartthrob. After meeting on the set of horror Se7en, Brad hooked up with another of his leading ladies, who was none other than Earth Mother and Goop blogger, Gwyneth Paltrow. The two were together for three years, even getting engaged, but the pair abruptly called it all off in the spring of 1997...
PA PhotosJennifer Aniston
However, you can’t keep a man that sexy down for long and sure enough Brad bounced back with America’s TV darling and good Friend Jennifer Aniston in 1998. With their matching honey-hued locks, they were every-inch the it couple, which was finally cemented when they married in 2000...
BRAD, ANGELINA AND JEN
PA PhotosAngelina Jolie
But of course, five short years later and the world was rocked by one of the biggest scandals in Celebdom. Although we thought that Brad’s playboy days were behind him, Jen and Brad got a quickie divorce in 2005 after rumours that he had hooked up with his on-screen wife Angelina Jolie in Mr and Mrs Smith. The rest, as they say, is history...
And now to the new class of Hollywood serial daters...
WennBradley Cooper
Despite earning hoards of fans as The Hangover hotty Phil, Bradley Cooper has long been the arm-candy of many of Hollywood's leading ladies...
WennJennifer Esposito
Before Bradley Cooper came to the attention of millions (of women) in The Hangover, he was Rachel McAdams' obnoxious boyfriend Doug in Wedding Crashers and a married man in real life. Indeed Coops married long-term girlfriend and actress Jennifer Esposito in 2006...
Getty ImagesCameron Diaz
...However, the couple filed for divorce just five months after tying the knot and soon enough Brad was spotted out and about with man-eater Cameron Diaz in 2007...
WennRenee Zellweger
...But it must have been a rebound as the couple staunchly maintained they were “just good friends” and by 2010 Bradley revealed he was in a full-blown relationship with Renee Zellweger...
PA PhotosOlivia Wilde
...However, the Hollywood heartbreaker and Bridget Jones actress called it quits in March 2011 and ladies man Bradley has since been spotted with a newly-single Olivia Wilde...
Rex FeaturesGerard Butler
Sexy Scotsman Gerard Butler first caught our attention in man-movie 300 (those abs), but just as quickly as he has made a name for himself as a Rom-Com stalwart, he has as one of the hottest dates in Celebville too.
PA PhotosJennifer Aniston
The hunky Brit’s powers of seduction were showcased when Butler played that time-honoured game of “are they or aren't they?” in 2009 with his The Bounty Hunter co-star Jennifer Aniston... Showmance or romance, we were still hooked...
Bigpicturesphoto.comLindsay Lohan
But the Hollywood hot rod cemented his Heartbreaker status when tales of late-night trysts with jail-bird Lindsay Lohan also surfaced in 2009...
GSI/ Barcroft MediaJessica Biel
After the LiLo rumours never really got off the ground and Jenn claimed they were “just good friends”, the love life of Gerard Butler seemed relatively sedate until pictures of him and co-star Jessica Biel enjoying scenic afternoons on his motorbike surfaced in the summer of 2011...
Rex FeaturesAshley Greene
...But as any Hollywood lothario should know, you’ve got to keep your audience guessing and we were certainly dumbfounded by reports that he had started romancing twenty-something Twilight star Ashley Greene. According to reports the 41-year-old Scotsman once serenaded 24-year-old Ashley with a rendition of Journey's Don't Stop Believin'...
...Okaaaaay.
PA PhotosJohn Mayer
...And from one of Jennifer Aniston’s beaus to another, our rundown of Hollywood serial daters, wouldn't be complete without singer John Mayer. Although relatively new to the scene, this guitar-toting playboy has wined and dined some of the finest A-list ladies...
PA PhotosJennifer Love Hewitt
Mayer’s first Hollywood leading lady was teen horror star Jennifer Love Hewitt. The pint-sized beauty briefly dated Mayer in 2002 and many have speculated that his song Your Body Is A Wonderland was a reference to Jen’s hot bod. However, always one to put his foot in his mouth, loose-lipped Mayer was forced to apologise to the actress after making jokes about their relationship on a comedy sketch show.
Rex FeaturesJessica Simpson
After Jessica Simpson had called time on her marriage to Nick Lachey, The Dukes of Hazzard actress dated John Mayer from 2006 to 2007. Although the romance didn’t last, singer-songwriter Mayer didn’t hold back when he spoke to Playboy about his former flame in 2010, telling the world that Jessica was like “sexual napalm” to him.
PA PhotosJennifer Aniston
But as a serial dater herself, it should have come as precious-little surprise when Jennifer Aniston started dating crooner John too. After a stop-start romance, John scrubbed up well and accompanied Jen to the 2009 Oscars, where she was forced to share the front row with ex Brad Pitt and Angelina Jolie. However, despite being a pillar of support, the two eventually called it quits when Mayer unceremoniously announced that he had dumped her. Nice.
Rex FeaturesTaylor Swift
Mayer was also briefly linked to country popstar Taylor Swift in the summer of 2010 but after a brief flurry of rumours, we’d pretty much forgotten about them. That was until the teen popster allegedly slammed her supposed former lover in a song called Dear John. Although never confirmed, Swift said of the song: "A lot of times when people's relationships end, they write an e-mail to that person and say everything that they wish they would have said. A lot of times they don't push send. This was a tough one to write, and I guess putting it on the album was pushing send."
PA PhotosAlex Rodriguez
Baseball's highest-earning star may not have been the most obvious Hollywood-heartbreaker but this sportsman has more than earned his dating stripes...
PA PhotosMadonna
...After the break-up of his marriage in 2008, ladies man A-Rod was linked to Mrs. Guy Ritchie - who put A-Rod firmly on the dating map. However, although nothing was ever confirmed, Madonna and husband Guy filed for divorce not long after...
Kate Hudson
...But after months of unfounded rumours linking the two persisted, Madonna stepped out with a toyboy model, while A-Rod got cosy with Rom-Com Queen Kate Hudson in 2009...
PA PhotosCameron Diaz
...But it was not to last and by 2010 the baseballing pro had ensnared another Hollywood babe and perma-batchelorette, Cameron Diaz, who broke rank with her fellow serial-daters when she gushed in mid-2011 that she loved A-Rod “too much”.
