Chelsea Handler in the Hamptons: ragged hell or not that bad?


These are photos of Chelsea Handler at the Memorial Day kick-off party in the Hamptons, sponsored (and for, I think) Hamptons Magazine. No, maybe the “kick-off” is for the “Hamptons season”…? Meaning that everybody who owns a house in the Hamptons opens it up officially on Memorial Day? Sure. Whatever. I don’t know Hamptons House Etiquette. I’m too busy eating baby seal pate on my yacht whilst rubbing diamond cream on my ass implants.

Anyway, Chelsea is the cover girl for Hamptons Magazine’s newest issue. Look at how nice the photo shoot is:



She looks almost pretty, very beachy and very much like her BFF Jennifer Aniston. Now look at the photos from the Memorial Day event. I mean… good God, was she on some kind of crazy bender and she just decided to show up to a party without sleep? She looks like a character actress with a meth problem who is constantly being typecast as “Crackhead #2” on various cop shows. The contrast between “the real Chelsea” and the ‘Shopped Chelsea on the cover is even more stark considering that they made her pose in front of the cover! Oh, cruel world. Cruel magazine!

By the way, in the interview with Hamptons Magazine, Chelsea called out P. Diddy, because apparently it’s like looking in a mirror or something. She tells the magazine: “P. Diddy was the only one I was like, ‘Get away from me.’ He’s so late all the time — maybe he won’t show up in the Hamptons until summer is over… [but] rappers are great interviews because they just don’t really care and they are willing to say anything. And I love that because that’s kind of how I am. They all hit on me. I love Pharrell and thought he was really sweet. Nelly, too.” No comment.




Photos courtesy of WENN.

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109 Responses to “Chelsea Handler in the Hamptons: ragged hell or not that bad?”

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  1. Macheath says:

    You know you’re hard when photoshop has trouble softening you up.

  2. silken_floss says:

    What a horrid woman.

  3. Kaboom says:

    She looks as if Claudia Schiffer first went on a Supersize-Me Bender and then on crystal meth for two years.

  4. Lantana says:

    She looks good – if she was 48. But that’s not how old she claims to be, now, is it?
    Had to go back and edit after it posted – lol @kaboom!

  5. SolitaryAngel says:

    Her hair looks like 8 shades of shit. >_<

  6. Louise says:

    Huge mistake to stand next to a photoshopped to hell picture. She says she’s 34 or 35. And people claim she looks better than Angelina Jolie.

  7. mln76 says:

    Wow I hope she forgot to brush her hair because if that’s on purpose someone really hates her. There is no way this woman is a year older than me she looks like she’s pushing a hard living 50.

  8. mia girl says:

    I do not understand this woman’s personal style?!! It confounds me and ultimately, disturbs me.

  9. You don't say says:

    She looks harder and more disheveled than usual, if that is possible, especially standing next to the “photoshopped into another person” photo. She also has an odd wonky eye going on. What is going on with her hair and if this is what the sun does to a person, she should stay in the shade.

  10. Katalina says:

    It’s the teeth that are freaking me out. She looks like she’s wearing my grandma’s dentures.
    Her teeth don’t usually look like this, do they??

  11. DianaPrince says:

    She says she’s 34 or 35.

    Maybe.. if she was born in a leap year. If not she certainly must have some kind of affliction. People who are 34 or 35 don’t normally look like they were born 50 years ago.

  12. the original bellaluna says:

    What in the name of Fried Hair Hell is going on with all the over-bleached, over-processed hair lately?

    @ Kaiser – You so funny! But the Hamptons season officially begins Memorial Day weekend and ends Labour Day weekend – if my understanding is correct.

  13. serena says:

    how ugly.

  14. Quest says:

    This is one time I have to say – thank god for Photoshop.

  15. Judy says:

    Does her grandmother know Chelsea took her dress? Sorry but I can’t stand her and think she’s a piece of trash. She’s coarse and crude and the definition of Fugly.

  16. Your mama says:

    The hair! The hair needs a lot of conditioner and a brush. Maybe if it was slicked back in a ponytail – the whole style would be better. She looks like she bleached it with clorox and ran out w/out brushing it.

  17. uknowuloveme says:

    she looks like a denizen from a”My Chemical Romance” video..yuck yuck

  18. 6 says:

    As a poster mentioned above, I thought the lead pic was of a rough Claudia Schiffer. Ooops!

  19. tango says:

    That dress! That hair! That face! She looks like she’s 55 years old and rode hard and put up wet. She needs to lay off the booze and drugs.

  20. poster 1 says:

    my god she has a really wonky eye. :/

  21. constance says:

    side pose ftw! Full frontal poses in that awfully cut dress look terrible!

  22. Nikkers says:

    @kaboom — lol, that’s exactly what she looks like

  23. aenflex says:

    f’ing ragged as hell

  24. Ron says:

    Chelsea dear, make-up is an option for women like Cindy Crawford or Charlize Theron, you my dear, NEED fcuking makeup. NEED IT!!

  25. RHONYC says:

    oh, Chealsea.

    smmfh 🙁

  26. PICOPINK says:

    Looks like she rolled out of bed and threw on some clothes after a bender. Sad and pathetic.

  27. MrsRut says:

    @Katalina…It is her teeth that look so bad! I don’t think they normally look like this. Her gap looks bigger and they just look jacked. Not sure what is going on. Also, one thing to note to everyone…She did say she was 34 or 35, but wasn’t that several years ago? So, she would be like 38 or 39. Pretty sure someone from her childhood would have called her out in the press by now if she were lying.

  28. Mia says:

    Damn. Girlfriend looks rough as hell.

  29. Eve says:

    I think somebody said this before here…that she’s 35 in dog years.

  30. Kloops says:

    Note to self: stop drinking immediately. ((shudder))

  31. lily says:

    Looks like all the nasty things she said about people reflected back on her face. What a mean and nasty person. Comedian or not she is downright a very insensitive, mean, rude, crude and a vulgar person. She is 35???? It is in leap year no doubt.

  32. the original bellaluna says:

    The way it works with Chelsea’s age is this: every time she claims she’s 35 (or 34; whatever) we deduct one year from OUR age. (FYI – I am now 17, I think.) Kind of like a drinking game, but it actually works to our advantage.

  33. Crash2GO2 says:

    Ragged as hell.

  34. Eve says:

    @ Original Bellaluna:

    The way it works with Chelsea’s age is this: every time she claims she’s 35 (or 34; whatever) we deduct one year from OUR age.(FYI – I am now 17, I think.)


    Kind of like a drinking game, but it actually works to our advantage.

    YAY! I’m going to play that game from now on.

  35. Jazz says:

    Holy ragged hell!! Time to step away from the vodka bottle.

  36. vanessa says:

    Wow every picture I see of her she looks worse than the last one..what is up with her teeth?? Her stylist must hate her to let her look like that…

  37. Testarosa says:

    I am usually all for celebs NOT having a stylist (whereby things like personality, quirks and spontaneity are allowed to shine through). In this case, however, I’m going to have to make an exception. In a word, EGADS!

  38. Anastasia says:

    If she claimed she was 70, everyone would be all “wow, she looks great for 70!” But no, she’s ACTUALLY 35. Shit, woman. Helen Mirren could be your younger sister.

    My Official Makeover Advice For Chelsea Handler:

    1. Deep conditioning and a new style for that hair, PRONTO.

    2. Sunblock, 100+ SPF, always. Sunglasses and hats, darling. The sun hates your fair skin.

    3. Get over your hatred of eye makeup. A teeny bit would look nice. Your eyes look like pin holes. Just a tiny bit of soft brown eyeliner, nothing harsh, but your eyes disppear without a smudge of liner.

    4. It looks like you might be experimenting with cheek implants. Stop that.

    Really, if she just did those things, it would be a vast improvement. She looks like 40 miles of bad road, and you shouldn’t look that hard at 35 or 36, seriously.

  39. Peachy says:

    Just checked MapQuest. Didn’t realize you must travel “100 Miles of Bad Road” to reach the Hamptons!

  40. Anastasia says:

    Oh and if this is also due to drinking too much and sleeping too little, girlfriend needs to lay off that for a while, too. Have one screwdriver instead of six and go to bed early.

  41. MikeyAngel says:

    She has smoker’s teeth for sure (smoker’s dont be offended, unfortunately that is how my mom’s teeth look).

  42. The Truth Fairy says:

    She doesn’t look bad for 50. Oh, wait ……

  43. NoFrank says:

    Oh my God, the HAIR! WTF? You’ve got money, Chelsea, do something with that nasty fried mess on your head. You look like a checker at Wal Mart in Tulsa, for God’s sake.

  44. anonymoose says:

    at least her clothes look pretty, in nice contrast to the awful outfits she wears on her tv show. no more stripes, chelsea, no more stripes!

  45. hairball says:

    Every time I see her on her show, it is so distracting how much I think she should have lip color and eye color.

    I’m not a big make up person, but every show she has pale lips and eyes and I spend the show thinking how much better she would look with darker eye shadow and darker lips.

  46. Judy says:

    She’s 35 like Kirstie Alley is a Size 6.

  47. Cheyenne says:

    Tore up from the floor up.

  48. Sasha says:

    She looks in the photoshoot like sienna miller in 5 years.

  49. Trillion says:

    Wow. She’s brave. Not in the good way.

  50. Maureen says:

    She look raggedy as hell. The magazine picture look very photoshopped. I think her age is more near 40 years old.

  51. Eve says:

    @ Judy:

    She’s 35 like Kirstie Alley is a Size 6.

    And I’m 5’11”!!!

    LOL! Some great comments on here today.

  52. Kim says:

    EGads! She looks terrible. I never noticed how bad her teeth are. She looks like Chaka from Land of the Lost.

  53. Skuddles says:

    Rugged hell for sure, and by the looks of those meaty arms – running to fat.

  54. Skuddles says:

    Ha ha, just realized I wrote rugged hell instead of ragged hell doh! But maybe in this case it applies – she does have a rather mannish air about her…butch bitch?

  55. Jeannified says:

    She looks like Claudia Schiffer with no make up on.

  56. Ally says:

    She could eat an apple through a picket fence.

  57. Charlotte says:


  58. Amanda G says:

    I guess I’m not seeing what everyone else is because I think she looks natural and quite beautiful in those pictures.

  59. wtf? says:

    what is up with the hollyweird meth look?

    goodgawd is this a new trend?

    .. its katie holmes clothing meets charlie sheen …

    kravitz and fassey yesterday now chandler

  60. sandy#1 says:

    first of all, lol at the comments here today, too funny, she gives it, she should be able to take it, i do hope she take these advice for a better Chelsea. i think every thing has been covered here.

  61. loveyourwork says:

    I haven’t laughed this hard at a thread in weeks. “your eyes look like pin holes”

    Anastasia – props. that was an amazing post.

    Amanda G – KILLING IT with “looks natural and quite beautiful in those pictures.”

  62. Stacia says:

    HOW?? could she grace the cover of any magazine. This woman is totally jacked up..discolored spaced out teeth, crows feet, grandma clothes and luggage under her eyes. You can tell that she smokes. What a rough looking 35 she is.

  63. Runs with Scissors says:

    looks like she’s trying to be all Aniston-y here, major fail! They both need to fire Huvane, not doing them any favors.

    @Kaboom, “she looks as if Claudia Schiffer first went on a Supersize-Me Bender and then on crystal meth for two years.”

    @Trillion:”Wow. She’s brave. Not in the good way.”

    @Ally: “she could eat an apple through a picket fence.”

    too funny, thanks for the laughs

  64. kris says:

    I think Nelly & Pharrell were just being nice.. I think they didn’t really know what to make of her.. she acts so crazy.. I wonder if they think all white girls are like that?!..

  65. lisa says:

    What you are on the inside is reflected on the outside.

    Good to see that this is still true..

  66. Cheyenne says:

    That hair looks very Laura Dern-y.

    They both look like they’ve been rode hard and put away wet.

  67. sapphire says:

    ROUGH. And obviously on her first season in the Hamps. Arriviste.

  68. Kiska says:

    She hasn’t aged well if she is indeed 35 or 36 years old.

  69. June says:

    Maybe she’s just “pranking” everybody with this look?

  70. anon says:

    Well, if she was a man, no one would care what she looks like as long as she does her job. I like her show and I like her, who cares what she looks like. Don’t be so stupid and judgemental, like we’re supposed to reward idiot, useless women based on the way they look and ignore smart, funny women as they have try to change themselves to fit into whatever stupid standard is in fashion. Male comedians don’t have to.

  71. MB says:

    Yikes! I co-sign everything that has already been said.

  72. anon says:

    People bashing her just sound like a bunch of jealous, petty dips. Why not analyze what David Letterman or some other male hosts look like? Are they all lookers to you or does their pocket book make you swoon? She’s funny and female’s don’t have to be “nice,” while men can say and do whatever they want. Grow up.

  73. B says:

    she’s a mess

  74. BB says:

    That’s a huge difference, ouch. And even if she weren’t compared to a photoshop version she just looks bad in general 🙁

  75. derekio says:

    Only thing worse than her looks…HER JOKES! this is one of those people I look at and wonder how in the hell she is a celebrity.

  76. anon says:

    All these people bashing her here, what are you? Dayshift hookers? Like to see you have such a strong opinion on how any male comedians look. Love her, she’s funny as hell.

  77. Daryl says:

    Bulemia mouth…or meth mouth…or dentures…or Abuela mouth…

  78. mln76 says:

    @anon 5:33 pm more like if she didn’t spend all her time making bitchy remarks about people (including little kids) we wouldn’t be so gleeful that she looks like doo-doo.

  79. Holyfrak says:

    She looks like Claudia Schiffer meets Courtney Love the morning after a four day bender.

  80. anon says:

    Darling, all the people she makes jokes about are in the public eye, selling themselves as “product.” Don’t be such a sucker, if the little kids are out in the public eye being pimped as products, blame their sleazy parents. There are plenty of great actors who’s personal lives you never hear about and kids you never see. It doesn’t matter what she looks like, there’s a grain of truth in most of her jokes, that’s why she’s so funny.

    May 31st, 2011 at 7:15 pm @anon 5:33 pm more like if she didn’t spend all her time making bitchy remarks about people (including little kids) we wouldn’t be so gleeful that she looks like doo-doo.

  81. Rog says:

    Ragged hell. Unquestionably.

  82. mln76 says:

    Fine anon I’ll play by your rules (although she swore up and down to Katie Couric that she’s never made fun if kids). But let’s just say Letterman does a joke about cheating we have the right to call him out as a Shithead since he cheated on his wife. Same if Leno makes fun of a backstabbing brown noser we all get to call him out (also if Jimmy Fallon makes fun of someone being too adorable )….Handler looks like doo-doo she’s not very funny and she either lies about her age or is a strung out coke ho or both she got her show because she screwed a married exec and has maintained her profile by getting in bed with the publicist from hell….So yeah I feel zero guilt on calling her out for looking like kaka.

  83. moptop says:

    Wow. Somebody knew what they were doing when they made her pose beside the magazine cover. Somebody who hates her.

  84. Camille says:


  85. Sue says:

    She reminds me of Kate Gosselin bad dresser and attention whore trying too hard to be famous, while Kate pimps out her kids Chelsea pimps out her friendship with Jen.

    anon@ who the hell would be jealous of her? Courtney Love crack out self looks better the Chelsea and has more talent.

  86. Mrs. Odie 2 says:

    She spends her time making bitchy comments because she’s a comic. She gets shit for it because she’s a woman and it’s a man’s domain. Women are supposed to be pretty, sweet, and young. Or if they cannot be, they need to stay hidden away.

  87. rissa says:

    she has lindsay lohan hair

  88. Super Awful says:

    She looks like Alfred E. Neuman in these.

  89. whitedaisy says:

    Mrs. Odie 2 and anon:

    Chelsea Handler gets Sh*t about her appearance because she dishes it out. And the majority of us here, find her to be into snark and shock as opposed to clever and humorous. The woman is not funny.
    If she can’t handle the heat then she needs to drop out of the limelight she so eagerly pursues (you rarely see Letterman or Leno on magazine covers and never shooting off their mouth on random topics at every opportunity or twittering photos of their latest conquest while in bed) and go back to her non-televised days of bookwriting.

  90. whitedaisy says:

    P.S. She is a hag.

  91. Noni says:

    I agree, she does look rough here. That said, I was standing next to her once in a hotel lobby in Palm Springs and was actually surprised at how pretty and thin she was in person.

  92. lucy2 says:


  93. Laughternrain says:

    Mrs Odie2, being bitchy, and being a comic are opposites. They don’t don’t go together. Comics are not usually bitchy and evil and hateful. I think you have the definition of comic confused. But lets not have that stand in the way of women portraying themselves and their gender as bitches and fullfilling the stereotype.

  94. anon1000 says:

    chelsie is looking like her bff aniston here. guess jen gave her pointers on bleaching her hair to a ridiculous light blond with dark roots and covering the face like a rug. thanks jen!!!!

  95. taxi says:

    She’s a beast! This woman should go quietly into the night or get some plastic surgery & teeth implants.

  96. hamburgerhotdog says:

    Gatdamn! Them roots there look like they’ve been nuclear bleached, the face is lookin real-Planet-of-the-Apes, and them teefs aren’t lookin too friendly with each other!

    I’m not even going to discuss that…dress….

  97. Melinda says:

    @Mrs. Odie 2- I totally agree.

  98. nnn says:

    She looks like the character of the wicked witch, someone spoiled and rotten with inner bitterness.

    She is neither smart, nor intelligent nor funny. She is just obscene, vulgar, agressive and cater for the lowest common denominator with her over the top comments and basic loud cheap vulgar so called humour.

    Jay leno is less vulgar and yet he gets ridiculed for his physical traits and his chin.

    If this woman and her followers think her targets are fair game because they are all public goods, they should take it too LIKE THEY SUGGEST WE SHOULD cause Chelsea is sure a public good too aimed for mass consumption and she puts herself in the position to trigger contempt giving amunition to be targetted as well.

    If she can hide behind her comedic timing to justify the amount of uglines her diahrrea of the mouth is able to spout, we, the public can sure criticize like any public good from models to singers, to actresses to TV hosts, to princesses, ect… She doesn’t have any immunity, why should she benefits from it, anyway ? She is as public as the latest starlet out there and is like any target for public critic, contempt or adoration.

    She is ragged as an old prune who said she goes often to bars for boozing, has no intellect whatsoever, no sophistication, nasty face, nasty body, nasty mind. Just masculine ugly bitchiness personified.

  99. Julie says:

    Why are people disrespecting Claudia Schiffer? Chelsea is a hag! 50 cent must have been very desperate to go out with her – nasty piece of work abusing Angie and her kids. Photoshop was designed for normal people which foul mouthed chelsea is NOT.

  100. Charlotte says:

    @Mrs. Odie 2: Seriously! No, she most certainly doesn’t look hollywood glam here. But who cares at this point? She’s a comedian, not a silver screen actress. Really don’t buy that she’s in her mid-thirties, though.

  101. Lady D says:

    “She looks like she’s wearing my grandma’s dentures.”
    “you my dear, NEED fcuking makeup. NEED IT!!”
    “she’s 35 in dog years.”
    “Wow. She’s brave. Not in the good way”
    “She could eat an apple through a picket fence.”
    I’m laughing so hard I scared my cat right off the monitor, and woke up my son.. This thread is fricken hilarious.

  102. LaLaLoo says:

    Whoa…If she wasn’t so incredibly nasty to everyone, you could just say “poor thing”, but this is fugly at its fugliest. Nasty is as nasty does …. she looks like she acts, and that ain’t good.

  103. Dee says:

    She looks like she gave birth to Beavis (from Beavis&Butthead)! The face, the teeth, the hair…he is spittin image of her!

  104. Eve says:

    @ Whoever mentioned David Letterman of being an example of an asshole who doesn’t get bashed for his looks.

    He has never tried to look or show himself as “hot”. And I still think he’s a lot prettier and has aged a lot better than her (he’s 64 years old, looks “fresher” than she does here).

  105. Francesca says:

    The purple tank top peeking out from under that dress? with the hair!? and the brown leather clutch?? and the eyes, the eyes… this is what happens to middle aged women when they don’t care: it shows!!

  106. PJ King says:

    Y’know, I would LOVE to see pictures of all of you folks who leave such bitchy, rude comments. DO all of you look drop dead beautiful? Yeah, didn’t think so.

  107. nnn says:

    I am beautiful and i am pretty sure most people in here are prettier than this so called comedian.

    But even if we weren’t, there is no rule as to crititicize a ‘product’ based on how you look yourself.

    We still can have our taste which are by essence totally personal and legitimate wether we are beautiful or not.

    And a looking this post shown, most people in here agree that this woman is gross and ugly the same way she sounds gross and ugly.

  108. Eve says:

    @ Nnn:


    I was too lazy to answer the cheap, demagogic and overused “I’d love to see how you all look like” or the “I wonder how perfect you must be to criticize others” argument.

    Trust me, I’m a way prettier than this hag. Although that doesn’t say much because almost any woman out there is.

  109. Zzzzzzzzz says:

    Please. This woman dishes it out regularly with no qualms, so why should we give a damn about criticising her? She’s not funny and she looks awful. There is no way in holy hell this woman is in her mid-thirties. Who does she think she is kidding?