A Pictorial History Leonardo Dicaprio's Hottest Hook Ups

He wanted you to show him the blueprints. He asked if you could spare some timber. And he’s absolutely mindf**ked you the bejesus out of you with his past two theatrical releases. In short, Leo does what he wants when he wants, no questions asked. He’s one of the most versatile actors in cinema and quite possibly the best actor of his generation. Good looking (no homo), rich as all hell, and intelligent – when’s the last time he made a dud? On top of all that, he cares about big time issues like the environment and the blood diamond circuit. Manly yet sensitive. So, it should come as no surprise the guy’s got every woman (lesbians included) wanting to swap spit with him. Here’s just a small sampling of those that have been confirmed or rumored…

Bobbie Brown

She is best known for her appearance in the video for Warrant’s glam metal anthem “Cherry Pie.” Before that she won the Miss Louisiana Teen USA 1987 title and represented Louisiana in the Miss Teen USA 1987 won the spokesperson competition on Star Search a record thirteen times and has also starred in TV shows such as Married… with Children (she appeared in 3 episodes) and films such as Last Action Hero

Kidada Jones

Leo and Kidada reportedly hooked up in 1998. She’s the elder daughter of Quincy Jones, younger sister of actress Rashida Jones, sister-in-law of Forest Whitaker. She was recruited by designer Tommy Hilfiger after styling a Michael Jackson shoot for VIBE magazine and went on to appear in such fashion magazines as Elle, Vogue and Harper’s Bazaar. She also dated Tupac Shakur who was on his way to pick her up when he was gunned down. Her film debut was in The Faculty playing Usher’s on-screen girlfriend, but her scenes were deleted.

Emma Bunton aka Baby Spice

These two reportedly hooked up in 1998. He probably got sucked into that hook up when she told him he had “to get with her friends” to be her lover. My guess is Leo split when she thought the two of them should become one.

Emma Miller

When Leo and Bar took a good ol’ fashioned Ross and Rachel break in July 2009, Emma briefly came into the picture. She’s the ex-girlfriend of actor Jesse Metcalfe who credits include the film John Tucker Must Die and a guest starring role on Desperate Housewives. Not much can be found on Emma. One thing’s for sure: she’s not the deceased founder of the Australian Labor Party. Apparently, she doesn’t do any labor. Typical model!
See more of Emma here.

Brittany Daniel

Co-starred with Leo in 1995’s The Basketball Diaries. The two shared a sex scene together and were rumored to hook up off the set. Probably best known for her stint on TV’s Sweet Valley High in the mid-90s where she starred opposite her twin sister Cynthia, but also for her roles in films like Joe Dirt, Club Dread, Little Man, and White Chicks. Her TV credits include CW/BET’s The Game, and as Mac’s transgender hook up on “It’s Always Sunny In Philadelphia.” She most recently starred in “Skyline” and is reportedly dating Keenan Ivory Wayans.

Claire Danes

She dated Leo in 1995 when the two co-starred in Baz Luhrmann’s Romeo + Juliet, proving once again that on-set romance most often leads to off-set hook-ups. If a fake kiss can be that good, imagine it with some real emotion. It’s been reported her first on-screen kiss was before her first one in real life. Talk about pressure.

Helena Christensen

Helena’s was rumored to be dating Leo in 1997 right around the time Titanic released. She’s a Danish fashion model and former Victoria’s Secret Angel who won the Miss Denmark crown in 1986 and represented Denmark in Miss Universe 1986. In 1991, she starred in Chris Isaak’s music video for “Wicked Game“, which was on MTV’s “Sexiest Video of All-Time” list. It was also voted #4 on VH1’s “50 Sexiest Video Moments” and voted #13 on VH1’s “100 Greatest Videos”.

Linnea Dietrichson

This Danish bartender/model from London has appeared in GQ, Maxim, M!, and FHM. Some sites reported she though Leo “used cliché pick up lines”, gave “lifeless kisses”, and was an overall “dud in bed” after meeting him in a London pub. Seeing as Leo has been with a nation’s worth of hot women, we’d have to call bullsh*t. Feel free to tell her so on Facebook.  See more of Linnea at Maxim.

Sara Foster

Sara’s a model turned actress who played Vinny Chase’s hook up on Entourage and went on to star in the films “D.E.B.S”, “The Big Bounce”, and “Bachelor Party 2: The Last Temptation”. She now has a recurring role as Jen Clark on 90210. You might’ve also seen her in the 2005 Backstreet Boys music video for “Shape of My Heart”, because we know how much you heart them boy bands. She dated Leo after he broke up with Tom Brady’s owner Gisele Bundchen.

Natasha Henstridge

Natasha’s a Canadian fashion model turned actress who’s best known for her role as a seductive alien in the Species franchise and as Bruce Willis’ on-screen wife in The Whole Nine Yards and its sequel. No confirmation on when they hooked up, but my guess is when Species came out. Leo probably broke it off when she tried to spear his dome with her tongue. Talk about getting into your role.

Eva Herzigova

Eva’s a Czech model and actress who’s appeared in ads for Guess? along with the Victoria Secret catalog and Sports Illustrated. She also posed for Playboy in August 2004. She reportedly met Leo at the Man in the Iron Mask premiere then had a month long affair while married to Bon Jovi’s drummer. Looks like the Man in the Iron Mask visited the Man in the Little Boat. Who am I, Quagmire?

Amber Valetta

She appeared in ads for Louis Vuitton, Calvin Klein and Versace and hosted MTV’s House of Style with fellow model Shalom Harlow. Her film credits include “What Lies Beneath”, “The Family Man”, Hitch, Transporter 2, and Gamer starring Gerard Butler. Leo finally kept it domestic with this Arizona-born knockout. He’s denied hooking up with her, which is probably why he’s better than us, we’d pwn that sh*t.

Kendra Jade

Kendra’s a porn star who’s appeared in more than 40 adult films. You might’ve seen her on Sex Rehab with Dr. Drew and Sober House. A chick who likes to drink and bone? Ain’t nothin’ wrong with that! Somehow Kendra ends up in the middle of some pretty steamy affairs including rumors of a sex tape scandal with Jerry Springer and allegations of breaking up Britney Spears’ marriage to K-Fed. It’s unknown when Leo hooked up with Kendra, but she’s appeared on just about every list found on the web. Of course, most A-listers would deny smooshing with porn stars and for good reason, but not because of the reasons you’d think. Kendra supposedly called his Titanic “average”. Compared to the anacondas Kendra took down on set, “average” is an extraordinary compliment.

Bijou Phillips

Like many women on this list, Bijou got her start in modeling then made the eerily “smooth” transition over to acting and then of course singing. She’s appeared on the covers of Playboy, Stuff, Nylon, and Vogue. She was in Almost Famous, Bully (very underrated movie, btw), and the film adaptation of Chuck Pahlahniuk’s “Choke” (also underrated). She also recently guest starred on Raising Hope and Hawaii Five-O. FUN FACT: Her pop’s John Phillips of the band The Mamas & The Papas. Again, it’s unknown when these two bumped uglies, but if I had to guess it’d be around 2000 when Almost Famous hit theaters and she was on Maxim’s Hot 100. She’s now engaged to fellow Scientologist Danny Masterson.

Alicia Silverstone

Alicia popped up on the pop culture radar with her appearances in 3 Aerosmith videos over the span of ’93-’94. She put the fear of jailbait into you with her MTV Movie Award winning performance in 1993’s The Crush. Then she permanently sealed a place in your soul with 1995’s Clueless for which she won another round of MTV Movie Awards. Her next award win came in 1998 for her performance in Batman & Robin – a Razzie. Frickin’ Schumacher! Her extensive resume includes TV, film, theater, and magazine covers like Cosmo, Entertaiment Weekly, and Rolling Stone. From ’96-’02, she was on FHM’s list of the 100 Sexiest Women in the World. Leo bagged the Excess Baggage star after his break up with Kristin Zang.

Bridget Hall

Bridget’s a model from Arkansas who’s appeared in Vogue, Harper’s Bazaar, ELLE, Allure, and the Sports Illustrated Swimsuit Issue. She’s also done promotional work for Pepsi, Guess, Chanel, Gucci, Versace, and Polo Ralph Lauren. You might’ve also seen her doing a little turn on the catwalk in the Victoria’s Secret Fashion Shows of ’98, ’01, and ’02. Leo sure does love his models. They allegedly hooked up in 1995 – and it was reported Hall lost her virginity to Leo and found the sexperience “disappointing.” Well, duh, show me one person that had a f***tastic first time and I’ll show you a liar.
See her bodypaint pics from the SI Swimsuit issues here.

Juliette Lewis

Juliette was nominated for an Oscar and a Golden Globe for her performance in 1991’s Cape Fear. She delivers one of the best cigarette smoke exhales in the history of cinema in Old School when Luke Wilson catches her cheating. She played Audrey in National Lampoon’s Christmas Vacation in addition to roles in Kalifornia, Natural Born Killers, Strange Days, The Basketball Diaries, From Dusk till Dawn, and, more recently,Todd Phillips road trip comedy “Due Date”. She’s also a devout Scientologist. Hail Xenu, y’all. These two dated around the time they both starred in 1993’s “What’s Eating Gilbert Grape”. I don’t know the answer to that, but I do know what Gilbert Grape was eating. Hey-o!

Kristen Zang

Ah, yes. The one that got away. The heartbreaker. Everyone’s got one. Kristen Zang is Leo’s. The pair met in 1995 and were a couple for almost two years. People described her as, “the only woman who has come close to having DiCaprio all to herself”. Word has it she preemptively ended things because she knew he’d blow up after Titanic and didn’t want the hassle of dating a mega huge superstar. I mean after a while you just get tired of all the free sh*t, know what I mean?

Demi Moore

Leo reportedly hooked up with Demi when she was still married to Bruce Willis. Talk about balls. You ask 100 dudes who wins that fight, and I’d say 90-95% side with Dr. Die Hard. That might be the reason the world’s hottest MILF is a little more forgiving when Nikon spokesmodel Ashton strays.

Gisele Bundchen

These two dated from 2000-2005. Gisele’s list of reported conquests is SIGNIFICANTLY shorter than Leo’s. I guess when you’re called “The Biggest Star In Fashion History”, “The Top Model Icon of All Time”, “The 4th Most Powerful Person In the Fashion World”, and Rolling Stone calls you, “The Most Beautiful Girl In the World”, you have to be somewhat selective with the level of dong you pull in. Plus, supermodels in general are real protective of their privates. Newsflash, models – sex burns cals – especially random, dangerous intercourse. Anyway, she stole Pats QB Tom Brady from actress Bridget Moynahan and the two now have a child together.  I guess he’s pretty dreamy too, but not so much with the recent Justin Bieber-hairdo. Leo’s ‘ship with Gisele reportedly ended when he acted “cozy” with Sienna Miller at a party. Jeez. Almost 5 years together down the tubes because a fellow actor wanted you to feel how silky smooth her underwear was. Lighten up!

Paris Hilton

I mean… who hasn’t, am I right? That reminds me, Paris, we’re meeting at the Frying Pan at 10pm. Bring coke.


Naomi Campbell

I’m scared sh*tless of this broad. All those reports about her temper. I’d be legit worried she’d tear your c*ck off. I get bugged out when a girl bites me lip during a make out sesh.

Carmen Electra

For some reason, I always put Carmen in the same category as Pam Anderson but I feel like that’s unjustified and presumptuous. Carmen seems to have the edge when it comes to comedic chops having done stints in a bunch of spoof movies. She also had the envious task of filling monster shoes on MTV’s Singled Out when Jenny McCarthy left. Past conquests include Dennis Rodman, Dave Navarro, Prince, Tommy Lee, David Spade, and Joan Jett. You read that correctly: David Spade AND Joan Jett. I don’t think anyone else in the world can claim those 2 on the same list. Also, I need to hang with Dave Spade. I think I get why he gets so much amazing talent but I still need to see it firsthand.

Mariah Carey

This is another chick who I’d personally be a little hesitant to get involved with. Again, strictly based on bad press and word of mouth. I can see how someone could be interested, that music video for “Honey” still ranks in my top 100 sexiest, but it takes a certain kind of dude to tend to a diva. I’d imagine the one night stand / hook up would be off the charts but the aftermath would drive you gay.

Kate Moss

Kate’s known for her slight frame and her propensity for “snow”, “freeze”, “blast”, yayo, nose candy, etc. But, her list of accomplishments far exceed those two aforementioned labels. She frequently tops the Forbes list of top earning models along with placement on numerous men’s magazines annual sexiest lists. It’s never a dull moment when Kate’s on the scene. I’d be shocked if these 2 didn’t hook up.

Bar Refaeli

It is super uncanny how alike these two look when they were in their teens, at least, in the face. Anyway, Leo and Sports Illustrated Swimsuit Issue 2009 cover model Bar Refaeli met in November 2005 at a party for U2 in Las Vegas. Typical. Then they broke it off in the summer of 2009, but there’s speculation they’re back together. Is this a repeat of Leo’s tenure with Gisele? Who knows. But, Leo should probably keep a close eye on The Situation. That dude’s creepin’ on EVERYONE!

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