Leonardo DiCaprio ran into Gisele Bundchen at Madonna’s Oscar party

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People were really upset that Leonardo DiCaprio didn’t win the Best Actor Oscar. I’m not sure why people were mad – in restrospect, it really was Matthew McConaughey’s year, although Leo did give him a good run, and Leo walked away with some big awards too. So, console yourselves with this thought, Leo-loonies: Leo’s time will come. Maybe not next year, maybe not the year after, but he’ll win at some point. People just didn’t want him to get an Oscar for playing a white-collar criminal in a bloated Martin Scorsese film. But it will happen eventually. And hey, he scored a bunch of MTV Movie Award nominations. I know, that’s no consolation prize. I doubt Leo will even show up to the MTV Movie Awards.

Did you also know that Leo was in such a grump after the Oscars that he didn’t go to the Vanity Fair party? It’s true – but he did go to Madonna’s Oscar party, which is where he ran into his ex-girlfriend Giselen Bundchen.

Leonardo DiCaprio bumped into his ex Gisele Bündchen at Madonna’s Oscar party Sunday night.

Spies saw Leo, who had his new model girlfriend Toni Garrn on his arm, chatting with Gisele at the party at Guy Oseary’s mansion, while Toni “sat back to let Leo and Gisele talk.”

Fellow friendly exes Miranda Kerr and Orlando Bloom were also both there, “and seemed on good terms,” said our witness.

Meanwhile, Madonna was putting on a show: “She was literally grinding the dance floor.”

[From Page Six]

Is anyone else laughing at the idea of Toni Garrn “sitting back to let Leo and Gisele talk.” LOL. Imagine how intimidating Gisele is to all of the Victoria’s Secret model girlfriends that came after her. Gisele is the Pinnacle Model-Girlfriend. She is the girlfriend all other model-girlfriends get judged against for Leo. Gisele was the one who broke his heart, I believe. And what’s funny is that I bet Gisele has no hard feelings about Leo – she probably loved that they ran into each other and had a moment to talk. But what did Leo feel?

Also: you know that Leo and his new BFF Jonah Hill are going to work together again, right? They’re going to do a bio-pic of Richard Jewell, the man who was falsely accused of planting a bomb at the 1996 Atlanta Olympics. Jonah will play Jewell and Leo is the producer and supporting star. That’s how much Leo loves Jonah – he’s going to play second fiddle to Jonah and produce a star vehicle for Jonah. Anyway, Leo has lined up a screenwriter for the project: Billy Ray, who got an Oscar nomination for Captain Phillips.

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Photos courtesy of WENN.

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101 Responses to “Leonardo DiCaprio ran into Gisele Bundchen at Madonna’s Oscar party”

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  1. Jaderu says:

    “sat back to let Leo and Gisele talk.”
    LOOOOOL What is this cowdooky? lmao

    Love the retro Leo/Gisele pics though.

    And I doubt he’s swooning over his MTV nomination. Jennifer Aniston is nominated for the female version of the award. *snort
    #poorleo

    • magpie says:

      “sat back to let Leo and Gisele talk.”

      Of course, Toni knows the “not a lot of drama” gig.

    • Virgilia Coriolanus says:

      Dummy! I don’t give a flying f WHO my ex dated–I’m not going to come off as some sissy. At least stand next to him, while he’s talking to her.

      I don’t think Leo could handle me—because since I know that I have an expiration date, I’d be getting as much jewelry as I could out of him before he gave me the boot.

  2. blue marie says:

    I had forgotten how much I liked them together, she’s better off now though. And didn’t Leo break up with her, not the other way around?

    Anyway, I would like to see the movie on Jewell, but I don’t know that I can stomach 2 hours of Jonah.

    • V4Real says:

      “I had forgotten how much I liked them together, she’s better off now though. And didn’t Leo break up with her, not the other way around?”

      +1 The girl turned a year older and Leo bounced.

    • Bridget says:

      Didn’t she want to get married and start a family, and he just wanted to continue being Leo? If he didn’t end it, he drove her to it.

      • Snappyfish says:

        You are 100% correct . She wanted him to marry her & he wasn’t ready. She actually left Tom Brady a few times while they were dating to try & reunite w/Leo. Including a time she was in Miami w/Tom & friends, Leo had broken up with Bar , he called Gisele & she literally excused herself from the table, hailed a cab to MIA & flew to LAX. She returned to Boston later in the week & Leo returned to Bar. I’m guessing If he wanted her back he could have her.

        They were pretty together & if she had been patient I think they would be married now.

      • Jegede says:

        @Snappyfish
        Oooooooh. – Anymore deets Snappyfish??

      • MD says:

        You are 100% wrong, Snappyfish. Gisele loves Tom. Love at first sight.

      • Teri says:

        I don’t buy her hooking up with Leo while dating Brady. She seems very happy with Brady. Leo clearly didn’t want to settle down and she was smart enough to see this and ended the relationship. She enjoyed being single for a year and then met Tom Brady and the rest is history.

      • Val says:

        Yes Snappyfish, tell us more tell us more!

      • MD says:

        Val: What do you want to know? Lies? Snappyfish is wrong.
        “No, I am not engaged and I was never engaged,” she says, laughing. “I do not understand why everyone wants to marry me [off]. Does everyone want to get rid of me so fast? I am only 24.” – Gisele.

    • j.eyre says:

      They sure are purty together.

    • Esmom says:

      They did make a lovely couple, I had forgotten.

      Agree about Jewell and Jonah, ugh. I can imagine he’s got Oscar already on his mind for that role, too.

    • GlimmerBunny says:

      I loved Leo and Gisele together. He seemed so in love with her, and I feel like dating one blond VS model after another is just an attempt to replace her.

      • Lilacflowers says:

        Then he shouldn’t have dumped her.

      • drunk says:

        Lilacflowers: Are you kidding?
        According to a source cited by Star, the 33-year-old calls Gisele, 27, after he’s had few too many drinks. Is Leo really still drunk dialing Gisele?
        “It’s like he just needs to hear her voice,” says the source. “I think he never thought she’d walk away.”

  3. hiddlesgirl85 says:

    These pics are reminding me of how good looking Leo used to be! Geez — he has not aged well.

    • Jaderu says:

      Ahhh the good ol’ days. Leo is sliding face first into the Jack Nicholson finish line.

    • Chicagogurl says:

      OMG This! What has he been doing to gain all those bags and wrinkles? He needs some vitamins, sunblock and sleep stat. Time to give up bad boy habits.

      • Virgilia Coriolanus says:

        It’s all that drinking. That’s why his face doesn’t look like hell on a movie set. He needs to quit pontificating about how he’s never done drugs, and quit the booze. My mom drinks a lot–almost every day–but she never gets drunk, and her face is never puffy.

      • Val says:

        You can really tell that he doesn’t work out or take care of his looks – the drinking, smoking, being a hedonist doesn’t give you a pass after 35… you need to work to look good, and Leo isn’t into that.
        The only time he worked out was the Departed/Blood Diamond era, otherwise you can totally see it that he’s uninterested in sports. (Unless it’s basketball… which he sucks at *snark*)

    • Anna says:

      Oh my his head looks like Megamind now in comparison to these old pictures! I knew it has gotten bigger but wow haha

  4. Eleonor says:

    I’ve always thought Leo broke up with Gisele because at a certain point Gisele wanted to get married and have kids, which is like kryptonite to Leo just as it is to George Clooney.

  5. paola says:

    I really can’t stand Jonah Hill.

  6. Tapioca says:

    Nope. I have never understood the “killer body” gushing – if you could pick your dream figure wouldn’t you want a waist, boobs and rounded hips?

    I seriously doubt Leo misses all the judgement and helpful hints to make himself a better person!

    • Luna says:

      No, i would want her body

    • GoodNamesAllTaken says:

      I would trade for mine, though. Lol

    • mercy says:

      She’ds too thin for my tastes, but most runway models are.

      He could’ve probably used some of that help, tbh. I get the feeling the current model doesn’t care and anyone who challenges him is shown the door, provided they don’t leave first.

    • mariah says:

      Her modeling career and success in 2 months is greater than all his model girlfriends combined. (although Toni is pretty in demand in fashion, but not to the extent of Gisele ever is/was). Bar and Erin are jokes career wise. Pretty sure thats what she meant…Gisele is the pinnacle of modeling, period. In fact Erin and Toni have said Gisele was the model they looked up too. google it, lol. Bar was the only one who acted b*tchy towards her.

    • MD says:

      Her body is perfect!

    • Virgilia Coriolanus says:

      @Mariah
      Bar lasted the longest after Gisele–so maybe he likes bitchy women. I don’t like Gisele….there’s something that’s so judgy about her. I do think she’s a good mom, loves her family, etc. But she’s not someone I would want to hang around with.

    • Miss M says:

      @Mariah: You’re right about Bar. Didn’t Gisele hang out with Leo’ s mom while he was dating Bar?! By the way, after Leo Gisele dated Kelly Slater briefly. Guess what?! Bar did too in one of the times she and Leo were broken up. It seems she kept taking Gisele’s leftovers.

    • Allie says:

      I agree! Her body looks like a preteen.

  7. yennefer says:

    Wow, was the party themed “The Ultimate Exes Party: Supermodels, Multiple Oscar Losers and Out-Of-Date Popstars With Some Baked Ham On The Menu”? Or did they simply have some kind of door to the past?

  8. hiddlesgirl85 says:

    Can you get more info about Madonna’s party? It sounds like all the high-profile stars from this year’s Academy Awards were there (including Brad and Angelina). I am itching to get some juicy gossip about who was hanging out with whom. So far, I’ve read that Brad and Angie were hanging tight with Ellen, Leo and Gisselle bumped into one another and chatted, and Sean and Charlize were making out like a high school couple.

    In fact, it would also be interesting if all the Celebitchy gals/commenters replied with all of the gossip they also heard. Maybe we can all put together a great narrative about the party as well.

    • paola says:

      Jared said his mum was dancing like crazy with Madonna and that obviously made his night (and the Oscar too of course).

    • Liv says:

      Just imagine you are a celebrity at the party and you watch all the others going off. Epic.

  9. Size Does Matter says:

    Curious – who has highest net worth: Leo, Gisele, or Tom Brady? I’m guessing Leo because of career longevity.

    • hiddlesgirl85 says:

      I agree — Leo.

    • Jedi says:

      Gisele out-earned Brady for the past few years, so she may be the winner in that battle…
      I think she owns a few companies in Brazil and has some pretty lucrative endorsements going.

      • AG-UK says:

        Giselle made $46m last year and the year before as well. Her was is gorgeous in these photos.

    • mercy says:

      Leo, probably. His Inception deal alone was rumoured to have earned him somewhere in the neighbourhood of 75 million. But Gisele is probably not that far behind. Money doesn’t buy happiness, but she seems very content with her family.

    • pink says:

      Gisele – Leo – Tom

      Gisele has many other business, not only modeling money.
      Leo’s net worth is about $ 250 million, maybe a bit more.

    • Lilacflowers says:

      Giselle. Not only does she earn high figures but she has invested very, very well.

  10. Lindsey says:

    Pre-Pumpkin Face Leo, good Lord.

  11. GIRLFACE says:

    I also think Leo’s time will come and I’m not concerned about him being in great movies in the future and continuing to be awesome. The Oscar is his real life Daisy, he kind of needs it in a weird way to be Leo. I want him to win sooner than later but he will one day. Gisele is really the hottest model of the model girlfriends and the most likable. I also got the feeling she wanted to settle down and he balked. I don’t think it broke his heart though.

  12. pfeiffer87 says:

    ‘Did you also know that Leo was in such a grump after the Oscars that he didn’t go to the Vanity Fair party?’

    Wasn’t there a post on this site a few days ago about how loads of A-list celebs didn’t go to the vanity fair party? Were they all in a grump too?

  13. Jegede says:

    Gisele actually gave an interview to GQ in 2006 implying Leo broke her heart.

    These pics remaind that she remains the only girl Leo ever took on a red carpet and acknowledged her existence alongside him.

    Its good they are friends now but there were stories of them ignoring each other in public in NY when she got with Tom, – suggesting residual feelings I suppose.
    Funny enough there were also stories of them booty calling each other for a while, in People and US Weekly, and there are pictures of Gisele hanging with Leo’s mom post break up in 2006, 2008 and (even 2009 when she had married Tom Brady!!).

    But time heals

  14. Bridget says:

    Like him or not, there’s no denying that Leonardo DiCaprio gets pretty much everything he wants – movie roles, women, parties – EXCEPT that Oscar. I wonder if anything has been denied him in decades, cause he’s certainly not used to hearing ‘no’. Until he pulls out something so spectacular that they can’t possibly say no, I think the Academy is just going to make him wait as long as possible, because who wants to reward the guy who already has everything?

    • Relli says:

      Right, I also think he will get it for being a producer or supporting actor.

      • Bridget says:

        I would be surprised if it happened even as a producer: he takes very few risks and typically works with a handful od extremely established directors. He’s not the guy going out and doing interesting work with interesting new talent. Lots of prestige there, but not an awful lot of freshness. They’re all overly-serious prestige showcases for him. And he doesn’t do supporting jobs (obvsly aside from the Richard Jewell thing). What was the last movie he took a real supporting part in? Gilbert Grape?

      • Relli says:

        @ Bridget, great points! I just don’t think they will give it to him for best actor because he wants it so bad. So I think producer or supporting at his best options. I think a lot of the resistence and possible aversion within the academy is because he has always bucked the system and did it his own way.

        Personally I love the dude and think he is a great actor, despite his pussy posse mentality. But there are many movies he should have already won for but didn’t or wasn’t nominated.

      • magpie says:

        Exactly! He is not a brave actor. I don’t think he has what it takes to accept a role that really takes him out of his comfort zone.

      • mercy says:

        @Bridget,

        Django Unchained was a supporting role. I agree he tends make safer choices than the types of roles that typically take home the Oscar, but Calvin Candie wasn’t one of them. He said Wolf of Wall Street was big risk during his Oscar campaign, but was it a worthwhile one? Maybe that was the thinking of some voters who were turned off by the subject and saw the film as excess for the sake of excess.

      • Bridget says:

        @mercy – i forgot about Django, though its still a very, very rare occurance. And I think he’s the only one that would have considered a Scorsese film a risk. It was only risky because it wasn’t really a story that needed to be told.

    • TG says:

      I wonder if during Leo’s next Oscar campaign if he will trot out a hired girlfriend like Clooney does to appeal to the conservative voters.

      • Bridget says:

        It doesn’t help that he’s not the most charismatic guy. He’s skated by on his once spectacular good looks for a long, long time. He’s is an excellent actor, but he’s not exactly out there charming the voters.

  15. PHD gossip says:

    I don’t believe Gisele broke Leo’s heart at all. That was Blake Lively who played Leo (and no one plays Leo). When Leo dated Gisele – she was “just” a model and he was the biggest superstar on the planet. After 5 years, it ran its course. I always suspected it was more of a PR relationship that a real one (If one read the VF interview they did the writer implied it).

    • mercy says:

      I don’t know about breaking his heart, but I can believe she put a dent in his ego. Blake was older. She wasn’t going to stick around for years while he did his thing like the 19 and 20 year olds. People say Leo dumps his girlfriends after they turn 25, but I bet they start to get tired of his lifestyle and want more for themselves as they approach their mid-20′s.

      • Jegede says:

        @mercy
        “tired of his lifestyle”. LOL
        I think Leo puts his cards on the table in his relationships about what the end game, is its on them to choose to stay.
        US Weekly even wrote that many stages of his relationship with Bar was not exclusive
        Of course most choose to stay with an A list superstar for the perks, exposure, sex and the career booster. Till he dumps them

      • mercy says:

        ‘Lifestyle’ was my euphemism for womanising. They may not tire of the perks, unless they can get enough on their own without having to put up with the downside. I don’t know what cards he shows, but I bet it wasn’t all of them, at least not in the beginning. Maybe after the fact, and by now he probably doesn’t care, but I bet this wasn’t always the case. He wasn’t raised that way and you can tell he likes to think of himself as a good guy.

    • Jegede says:

      I was with you till the last line.
      Serious question why is EVERY Leo relationship descibed as PR? Does this happen to other non married actors or is it exclusive to Titanic Leo?

      People don’t like his choices so a conspiracy has to be attached to every girlfriend to rationalise it?.
      His choices seem obvious to me. He’s a typical manw_ore who likes attractive women – only with a preference for fair haired long legged gazelles models and actresses alike (the younger the better)! – See Rod Stewart, Will Carling e.t c
      Also his lovelife is a punchline at award shows and TV spots at this point why would he PR himself into the situation of being considered a joke!

      *Looking at his girlfriends, I personally belive Leo has an Oedipus Complex – dude wants to marry his mother

    • Harriet says:

      @PHD gossip which article are you referring to? Do you have a link?

    • GIRLFACE says:

      I don’t think Blake is intelligent enough or owns her beauty enough in a way to make Leo sad, I just don’t get that vibe from her. She’s a pretty girl with a nice body but she is no femme fatale. She may have played him but it seems more incidental than because she is some kind of mysterious seductress. I mean good grief, in interviews she is completely intolerable.

      • mercy says:

        “Seductress” lol, no, I don’t see that at all. I do think she’s probably smarter than some give her credit for. But I don’t think Leo gives a fig about intelligence, and his mum, career, and guy pals seem to own his heart.

    • mariah says:

      I think the rumors were true that she wanted to settle and he didn’t. Because look at their life paths now! She is settled. He is not. He is still loving the single life. I think that speaks volumes about it.

    • MD says:

      PHD gossip: No, Gisele wasn’t “just” a model. Gisele was Gisele. “he was the biggest superstar on the planet….” Are you kidding? The biggest superstar on the planet? The VF interview says Gisele broke up with him and he couldn’t believe Gisele dumped him. PR relationship? I don’t remember it!

  16. pink says:

    1- Actually, Leo went to the vanity fair party. There are plenty of photos to prove.

    2 – I wanted Leo to win, he was amazing. But overall this year was really strong.

    3 – I can’t wait to hear about his next project. I love Leo’s films.

  17. Maggie says:

    Leo will get his Oscar one day. I still find him extremely attractive.

  18. mariah says:

    I’m not surprised. They have both remained amicable and have said nice things about one another after their breakups. Gisele was even seen hanging out with his mother quite often at least 3 years post breakup! There was a rumor his mother sent baby gifts to Benjamin. Also there is a Brazilian Leo interview where they ask him about Gisele who had just had a baby and he said “Im so happy for her, shes a great person”. Gisele has also said Leo is a great person but they were better as friends rather than a couple. Now I dont think they call each other and hang out , LOL but they seem amicable.

  19. Snappyfish says:

    MD I think she does love Tom now. They were dating at the time & he(Tom) had his baby mama drama going on. This was years ago & I read that story here on CB. I’ve been around CB since the beginning. As I said she & Tom were just seeing each other & it does look as thought there was some overlap w/Brady dating both Gisele & Bridget. No biggy you are allowed to date multiple people until you commit.

    Not throwing shade just recounting a story. But I do think if she thought she could have gotten Leo down the aisle that is where she would be, again my opinion

    • Jegede says:

      I actually agree with you Snappyfish.
      I read the same years ago on other blogs and US Weekly et al alluded to it.

    • Christin says:

      There was a whole lot of drama back then. It was not exactly a seamless little fairytale (not that anything really is).

      I also think she would have stayed with Leo had he been open to marriage and family with her.

    • MD says:

      Snappyfish: I read the interview hours ago.
      They broke up in 2005. Gisele wasn’t looking for a relationship. At the end of 2006, she fell in love with Tom Brady. Tom had recently broken up with his girlfriend. They were dating two and a half months when Bridget announced that she was pregnant (February). But you are right, it wasn’t LOVE at first sight. She said love is something that grows, but there was a great feeling…

      • ToodySezHey says:

        Yeah, I agree with MD…I dont buy Snappyfish’s rendention of events. From the time Tom and G met, it was on like popcorn and Leo definitely did not seem in the mix.

        I remember clearly, Giselle showing up to a Patriots game and made no bones about the fact that she was there to see Tom. She was fairly gushing about it. I think I even recall her being on the sidelines talking to Tom after the game all smiles and flirty.

        A few months after that, the football season is over, Bridget is preggers…and Tom is flying with Giselle to vacay in Paris and admits to buying some nice expensive jewelry for Giselle.

        Fast forward a few months later and Tom gets hella flack from his mouth breathing Boston fans when 1) he is seen in NYC 2) he is seen in NYC with giselle….while wearing a Yankees cap!! And worse yet, its revealed he and G have a spot in NYC( for obvs reasons, girl is a model, she needs a crib in NYC, but try telling that to Tom’s Sam Addams-addle brained fan base) LOL. In the words of Dlisted, ESCANDALOSO!

        And I believe it was within a year of meeting/dating that Tom and G got engaged, and I dont recall it being a long engagement.

        So nawl…I dont think G gave a second thought to Leo once she met Tom.

  20. danielle says:

    I think the movie about Richard Jewell could be really good.

  21. BendyWindy says:

    Hmm. In two years will we be discussing “Jonah Hill, 3 time Oscar nominee, and friend Marty, Leo and Brange?”

    Oy.

  22. CassieWZ says:

    I think some of you should search Gisele’s dating history. After Leo and before Tom, she dated Kelly Slater. Gisele broke up with Leo in 2002 during this period she dated Ricardo Mansur. In 2003 Gisele and Leo were a couple again to break up for the last time in 2005.
    Everything is well recorded in pictures and press coverage.

    I’m also not surprised by Gisele and Leo to be in good terms socially, they both show respect to each other when their past relationship is questioned in interviews.

  23. raya says:

    They look like they had insane sexual chemistry. With Brady, she looks really happy as well, but just not quite as on fire.

    • bobbisue says:

      +1

    • ToodySezHey says:

      I dunno…I remember when she showed up at a Patriots game. After the game she was on the sidelines, and she looked all glowing and gushing talking and flirting with Tom Brady. She was pretty much down with him from the jump. I think part of the problem is, Tom is an athlete not an actor, so we dont get to see as many photos of them together. Not to mention if she is at a game she isnt courtside like most trophy wives, she is way up in a press box, if she is even at a game.

      I bet if we saw them more, we’d see the chemistry and attraction they have for one another.

  24. CynicalCeleste says:

    “… he’ll win at some point. People just didn’t want him to get an Oscar for playing a white-collar criminal in a bloated Martin Scorsese film.”
    This.

  25. JennB says:

    Where was Tom?

  26. bobbisue says:

    MD sounds like Gisele talking! “I don’t remember that!”

  27. Lady_Jane says:

    Unfortunately, I know many “Leo” types out and about. They are the ones that (alot of) women are irresistably attracted to/seduced to, whether it be a combo of looks/power/charm, but deep down inside they know their days are numbered and it’s only a matter of time before they get burned. Delusion sets in, that they are going to be the exception, the one that “changes them”, and it never happens. Moths to a flame with every moth getting burnt by the flame. Crazy isn’t it?

  28. Kosmos says:

    Yep, I remember Giselle and Leo, on and off again, mostly remember that he probably did not want marriage WITH ANYONE….so it appeared that she stuck it out for as long as she could and then they make a final breakup. Leo went on to date model after model, never committing, as usual, while Giselle probably did want marriage and children, so she found a willing partner in Tom Brady, but whether she really got over Leo, I don’t know. What I don’t understand, is why model after model have gone for Leo, knowing his track record and complete lack of commitment. Perhaps just being connected with him helps their career? Just not sure…..I only know that I would steer far away from a man who has had that many multiple relationships, no matter what his status is…..