Debra Messing in black Sobaski at the Tonys: lovely or uncomfortable & tweaked?

Debra Messing

Debra Messing walked the Tony Awards red carpet with her jumpoff (and “Smash” co-star), Will Chase (shown below), and I never thought about it until now but … “Will & Grace 2.” Debra looked like an awful mess last night in this Matthew Christopher Marchi Sobaski couture dress. Now the dress itself isn’t really the issue here but the way that Debra is wearing it. Okay, I take that back — the dress is part of the problem. I’m usually a sucker for an a-line party piece, but Debra looks altogether uncomfortable in this outfit, and the off-the-shoulder aspect isn’t helping matters. The black satin is also a bit too princessy and severe when coupled with Debra’s Croydon-facelift hairstyle.

Debra accessorized with strange Fred Leighton earrings and a girlish Judith leiber clutch. I used to enjoy Debra so much on television, and I remember when she was (fancifully) hailed as the second coming of Lucille Ball. But Lucille would have never injected her face with so many fillers and Botox variants. Oh, Debra.

Debra Messing

Debra Messing

Debra Messing

Jane Krakowski

Jane Krakowski looked saucy as always in a white Escada gown with plenty of sparkly sequins and a tiny faux-train. I feel like Jane wears this sort of dress all the time, but it really suits her although I think she’d look cute in spaghetti straps. Just a suggestion. This dress would have been slightly boring, but the slim belt breaks up the monotony. Janes hair and make up look lovely and appropriate for the occasion.

Jane Krakowski

Martha Plimpton

Martha Plimpton (and I confess to not really keeping up with her career since the late 1980s, aside from Beautiful Girls) presented last evening, and this is the most dressed up I’ve ever seen her. Martha wore a gorgeous red Lorena Sarbu crepe gown with a sheer embroidered overlay at the top. The dress’ cut is quite flattering to her figure, and her hair is still kind of 1980s, but that’s okay because I was so jealous of her for dating River Phoenix.

Martha Plimpton

Cyndi Lauper

Cyndi Lauper looked completely zonked out, and of course she dressed like a bit of a weirdo … she’s Cyndi! Asking Cyndi to dress in a conventional manner is like expecting Florence Welch to dress up like Katy Perry. It ain’t happening. Does Cyndi look a little bit wasted to you?

Cyndi Lauper

Photos courtesy of WENN

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86 Responses to “Debra Messing in black Sobaski at the Tonys: lovely or uncomfortable & tweaked?”

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  1. Tessa says:

    That dress is so unflattering on her. She was so rail thin when she played Grace, and now she’s not so much, she has to learn how to dress for her body. Not everything is going to work. This is not working. Her face looks fine to me. I wish she’d get a new show. I loved watching her every week. She’s so charming.

  2. Dawn says:

    They all look fine to me except for a minute there I thought Cindy Lauper was the woman who played Mrs. Costanza on Seinfeld.

  3. aims says:

    Debra’s face look really tight. It gives me a headache looking at her. Her dress looks like a bad bridesmaid dress. She was so pretty during the Will and Grace days. Jane looks great. Her dress is perfect for her body.

  4. Jag says:

    Except for Debra, I’d love to know who works on their faces, be it for laser treatments, skincare, and/or surgery. These ladies look great! I do love all the outfits, except Debra’s dress and Cindy’s pants.

    Cindy looks totally zonked out.

  5. Lisa says:

    Cyndi Lauper is my love. Someone please remind her that she looks amazing in colours other than black, too.

  6. Jenna says:

    Is Debra doing that smiling/Trya Banks eye-thing in the first two pictures, because it’s making me uncomfortable. o_O

  7. Charlotte says:

    Debra used to be so pretty. I remember thinking often how her beauty was largely unseen due to her being funny, much like Lucille (even though Debra was not at her level). Now she’s rather scary. Martha’s face looks much nicer and more natural.

  8. Dedrie says:

    Martha, Martha, Martha.. you are an insanely fabulous star.. the rest are only flaky imitation insane poof balls..

  9. lisa says:

    wow holy browlift debra! i guess her jump off likes the surprised look

    jane and martha look so much better and are about the same age as her

    cyndi is awesome, i will cosign just about anything for her

  10. TheOriginalKitten says:

    Jane looks awesome.

    That’s all I got.

  11. Audrey says:

    I’m so sad about smash getting cancelled. :(

    Idc that Katherine mcphee can’t act. I loved that show

    • GMarchetti says:

      “Idc that Katherine mcphee can’t act. I loved that show”.

      Can’t act, sing, or dance. Actually, I don’t know what she really can do. If Smash at least had a talented leading actress, I think it would have survived a little more, even with that mess of a writing.

      • lisa says:

        i would have liked to see more megan hilty and less kat

        there was one spot on review “mcphee takes a one note character and takes it down a half note”

      • GMarchetti says:

        “i would have liked to see more megan hilty and less kat”

        Me too.

        At least we got to see Megan as Marilyn (for good) and performing “Don’t Forget Me”. That song is so beautiful and really deserved to be sang properly, like Megan did.

        If only Marilyn could see (and hear) it…

      • Audrey says:

        I think she can sing

        But dancing and acting are out. I almost stopped watching cause her love life storyline was so unbelievable. She didn’t have chemistry with anyone. Poor Jeremy Jordan had to carry every scene with her

        I don’t much like megan hilty either though lol. Better than Katherine fwiw

    • BeesKness says:

      I loved to hate watch Smash, but it did start getting a little better the second season!! I’m a Broadway nut, so it was nice to see so many Broadway stars make cameo appearances. Katherine McPhee was so wooden and annoying that I started wishing the worst for Karen. I did really like Megan Hilty even though Ivy wasn’t the greatest character. RIP Smash :(

  12. Jem says:

    I think Debra’s tight face was just caused by her high hair-do.

  13. Jess says:

    I haven’t seen anything Debra’s done since Will & Grace. I would never have guessed that was her. Whoever did her make-up clearly hates her…

    Jane looks good.

    • Micki says:

      I don’t remember her in anything apart “The Wedding Date” and that was because of Dermot Mulroney.
      They had good chemistry there.

      • littlestar says:

        Sigh, LOVED that movie. Will have to watch it again at some point this summer :) .

      • Amanda_SB says:

        Yes, loved that movie, and it was because of Dermot Mulroney. It was a silly story, but still entertaining.

        Debra Messing either looks really good, or really bad. There is no in-between with her, unfortunately. She looked fab on Will & Grace and on the TV Mini-series The Starter Wife (I didn’t watch the series). I don’t care for the dress. It’s not flattering. She has been tweaked a bit too much and having her hair pulled so tighting on top of her head is not helping. She’s having an off day.

  14. janie says:

    Love Cyndi! I think she was really nervous.. Debra looked bizarre? Neil P.Harris looked hot! Just love him!

  15. Jen34 says:

    Jane looks amazing. I’ve always been a fan. That’s all I am going to say.

  16. Helen says:

    I love how Martha Plimpton is rockin’ an A on the red carpet, it’s so cool!

  17. cassius. says:

    Debra Messing could be the star in a Shelley Winters biopic.

  18. Micki says:

    Cyndi Lauper looks like a Batman after a dog fight.

  19. ctkat1 says:

    Debra doesn’t look great with a heavy makeup- see “The Wedding Date” for another example.

    Cyndi Lauper was so emotional and great when she won her Tony, I loved it.

    Martha Plimpton is awesome. I never really thought too much about her career (though I love “Parenthood” and “Beautiful Girls”), but she was featured in Rosanna Arquette’s documentary about women aging in Hollywood, “Searching for Debra Winger” and she was so smart/cool/interesting that I now love her.

  20. Sleepyjane says:

    Fillers, and Botox and crazy eyes – oh my!

  21. Miss so and so says:

    I think that part of the problem with Debra is her posture…. she slumps and it makes her look bigger and dumpy.

  22. Shelly says:

    Love Debra, but that outfit is terrible. So is her hair.

  23. UsedToBeLulu says:

    I love Debra, but her transformation confuses me. I think she might have struggled with an ED, because she was a rail during Will & Grace, so I’m not going to slam her on the weight gain. But she rocked her natural curls in that show – I miss them. And it looks to me like her face is still settling from some work.

    But there is no excuse for that dress and that bun.

  24. wowsa says:

    Debra’s hair is lovely, but she looks uncomfortable in the dress, like she picked up a few pounds and lacks confidence. Jane looks fantastic.

  25. Celeste says:

    Jane looks great, Cyndi’s neck shows her age, Debra has done too much to her face.
    Marta rocks! I love “Raising Hope”. Fantastic show.

  26. drdoolittling says:

    DM does not have the posture to do this dress justice. She is hunched over and her shoulders are down. You need shoulders pushed back, boobs pushed out; you need to own this dress and she doesn’t at all. Jane looks amazeballs.

  27. lucy2 says:

    Jane and Martha look awesome. Definitely keep up with Martha – Raising Hope is hilarious, and she’s also great when she guest stars on The Good Wife.

    Debra does look uncomfortable. I think bad makeup too, but if she did get something done I wonder if it was recent, I didn’t notice anything while she was on Smash. I like her though, I think she’s really pretty and she’s good on TV, but her role on Smash was not great.

  28. Quinn says:

    Blarf. Messing looks horrific.

  29. Catlady says:

    Cyndi Lauper’s facial expression in that last pic is TOTALLY channeling Gloria Swanson circa Sunset Boulevard!

  30. Oh says:

    Obviously I don’t know if it’s true, but the #1 guess for CDAN’s long-running blind item about ‘coke mom’ is Debra Messing. I think of that whenever I see her because whether it’s too-tight hairstyles or a brow lift, she always looks really crazy in the eye area to me.

    I also think she has taste issues – I’m guessing her weight still makes her very-thin-to-thin by any definition, but she tends towards overly juvenile styles and that will age a grown woman with a quickness.

    Martha P. looks so great. And Jane Krakowski: I adore her. She was so amazing on ’30 Rock,’ and she looks and dresses like a modern, relaxed take on a ’30s film star.

  31. aenflex says:

    Martha and Cyndi together? Sweet.

  32. Nerd Alert says:

    Jeeze how can you tell if she’s uncomfortable or not? Her face is frozen. I used to think she was so pretty, this makes me really sad.

    I love Jane!

    Yes, Cyndi looks like she’s on…something.

  33. taxi says:

    Is there any black eyeliner left in town?

    I think Cyndi’s lashes are too heavy for her to keep her eyes open.

  34. Anna-fo-Fanna says:

    Bedhead, you absolutely MUST check out “Raising Hope” with Martha Plimpton. It’s cute and funny and warm. One of my fave shows!

  35. Ron says:

    The dress is too young for her. It looks like a homecoming dress. On top of that it doesn’t fit well and it’s “couture”? Holy hell! If that is what this designer considers couture, starlets beware!

  36. islandwalker says:

    Love Martha P! Aging gracefully and naturally too.

  37. Apsutter says:

    The Tony’s were amazing!!! NPH did such a damned good job! There should be another post just dedicated to his wonderfulness and awesome opening and closing number. Also how he threw some major shade at the Les Mis movie!

  38. ladybert62 says:

    Ms. Messing who is usually beautiful – looks awful here. Her face looks frozen – she has that deer in the headlights look in her eyes and she looks fat in that dress.

  39. WTF says:

    Yeah, as much as I loved Will and Grace, I never got the appeal of Debra Messing. Whenever people talked about how beautiful she was/is I just thought people were responding to her wild awesome red hair. With it pulled back she’s just blah….

  40. skuddles says:

    Debra Messing’s dress makes her look squat, thick waisted, and dumpy. Big fashion fail.

    Cyndi Lauper, on the other hand, could wear a gunnysack and I’d still think she looks fabulous :)

  41. Maritza says:

    These women are no spring chickens therefore they look great! Debra Messing has clearly gained weight and they suit her just fine.

  42. BeesKness says:

    That second picture of Debra is nightmare inducing!

  43. Fred says:

    Debra looks simply awful, in every respect.

  44. Jennifer12 says:

    Wow, it’s the plastic parade. #depressing

  45. LahdidahBaby says:

    :-o Hold me, I’m scared.

  46. Anne says:

    Urgh! I’ve never liked Ms Messing since I had to sit near her in an airline club lounge where she was the sourest looking person in the room.

  47. Malificent says:

    Love Martha — super-talented and looks like a hoot to go drinking with.

    Debra needs to realize that the upside of middle-aged weight gain is that it makes your face look younger. If you’ve put on the pounds — why even mess with the fillers? I’m almost exactly her age — and Lord knows you can tell I like my extra piece of pie — but my face looks 10 years younger, even without any makeup on. Say “yes” to pie — “no” to botox.

  48. Kerrybear says:

    She definitely got plastic surgery. She used to have that fold of skin between her eyes, just above the bridge of her nose, and now it’s completely gone. I have the beginnings of the same fold and am hypersensitive to it so I notice it on other women. She definitely had it. I smell a brow lift.

  49. Mar says:

    Debra looks like she had an eye lift and she is very puffy. Cyndi Lauper looks fantastic!!!!

  50. Mar says:

    Debra looks like she had an eye lift and she is very puffy. Cyndi Lauper looks fantastic!!!! Aging must suck in Hollywood!

  51. colt13 says:

    I saw this thumbnail on another site and assumed it was Adele.

  52. amilu says:

    I love Martha Plimpton so much. She’s absolutely brilliant on Raising Hope. I’m so glad she got/took that role. I missed her!