When Awkward Strikes: Celebrity Moments That Keep Us Cringing


Since I’m still twitching from unwittingly bearing witness to American Idol alum Ace Young’s saccharine, obviously sponsored (he name-checked his jeweler!) sixth-grade-homecoming invitation of a proposal to Diana Degarmo on last night’s AI finale, there’s pretty much no way I could write a post about anything BUT this apparent celebrity penchant for embarrassing themselves beyond all comprehension. So, since misery loves company, take my hand and let’s walk down the most uncomfortable memory lane ever, shall we?

american idol propsal cringe 600x429 When Awkward Strikes: Celebrity Moments That Keep Us Cringing

I'm not sure whether this is before or after he plugged the jeweler.

Kicking it off with Ace and Diana — celebrities, write this down: if you have a ring in one hand and a microphone in the other, chances are you are embarrassing yourself, and us.  STOP IT. (There’s video of this American Idol proposal train wreck, if you feel like gouging your own eyes out.)

Angelina brother kiss cringe When Awkward Strikes: Celebrity Moments That Keep Us Cringing

Angelina makes us all want to barf by incessantly frenching her brother, James.

Ahhh, an oldie but a goodie. Remember when Angelia Jolie won that Oscar for Girl, Interrupted and would NOT STOP making out with her brother James?  Of course you do because it was totally disgusting and none of us will ever be able to un-sear that image from our fragile memories.  Celebrities, maybe write this down too: If the initial audience reaction is “EW! GROSS!” maybe just spare us all and move on, rather than continue to make everyone’s skin crawl by repeating the awkward offense time and time again.

Charlie Sheen Cringe When Awkward Strikes: Celebrity Moments That Keep Us Cringing

Charlie Sheen hopes his chair will protect him from 20/20's Andrea Channing.

Who hasn’t wanted to take a shower on behalf of Charlie Sheen?  I know I have, and never more so than when he told 20/20 that he had “Tiger blood and Adonis DNA”.  Most cringe-worthy moment of the whole debacle for me?  Thinking of a sober Charlie one day hearing himself say that his daughters would think his well-publicized hooker-binges are cool…or worse — his grown-up daughters hearing it.  (Want to relive the horror?  Hulu’s got Charlie Sheen’s unadulterated mania in all its glory.)

Tori Spellings Boobs When Awkward Strikes: Celebrity Moments That Keep Us Cringing

Oops.

Dean McDermott reminded us all to look before we tweet when he attempted to share a photo of son Liam joking around, but instead shared wife Tori Spelling’s bare breasts with the WHOLE INTERNET.  OMFG.  I can’t even begin to think about how hard I would punch my husband in the throat if he did that to me.  I’ve never been a huge fan of Donna Martin myself, but even I felt for the NoTORIous one when her nips went viral.

Ashlee Simpson Does Jig 600x452 When Awkward Strikes: Celebrity Moments That Keep Us Cringing

Ashlee Simpson makes it worse by doing a jig.

It’s almost as cliché as Janet Jackson’s wardrobe malfunction and yet Ashlee Simpson’s Milli Vanilli moment on SNL has got to be one of the most truly, deeply humiliating moments in celebrity on-air history.  Jess’s little sister was just a wee pop star when her song started to repeat while she and her band stood on-stage like kids who just walked in on their parents doing it.  Ashlee seems to have recovered, but I’m pretty sure the incident left me with a few grey hairs.

David Hasselhoff Cheeseburger When Awkward Strikes: Celebrity Moments That Keep Us Cringing

Don't bother me. I'm eating.

Okay, so I know he never meant for this intimate family moment to be watched by millions, but of all the ways David Hasselhoff could have seen his name turned into a verb, I bet he never thought it would be in the context of drunken cheeseburger eating.  Now, when frat boys across America “Hasselhoff” that Breakfast Jack at 3am, they have David’s fed-up teenage daughter to thank for it.

…And that brings us to the conclusion of this incredibly unsettling edition of Celebrity Moments that keep us cringing.  If I’ve missed a doozie, please bring it to our attention in the comments.

 

source, source, source, source, source, source 

About The 818

Morgan Shanahan is a professional blogger and screenwriter living in Los Angeles’ San Fernando Valley (aka “The818”) with her toddler daughter, dashing hubby, and farting trio of dogs. In addition to over-sharing her personal life (complete with curse words) on The818.com, she's also BlogHer's Entertainment Editor, and writes occasionally about art and design for Cargoh.com. She also tweets, pins, and instagrams.



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  • http://twitter.com/thegrumbles the grumbles

    bahahahaha the Hoff. oh man. good times.

  • http://twitter.com/babyrabies Jill Krause

    OMG WHAT WAS THAT LAST NIGHT?!  I was truly shocked and horrified. And squealing like a school girl, alternating hiding my eyes and letting my mouth hang open.

    • Morgan (The818)

      It was like getting your first period on stage during a school assembly.

  • http://theheirtoblair.com/ Beth Anne

    I am laughing so hard that I’m crying.

    OMG, that proposal.

  • Snarky_Amber

    I swear, Ace must have taken all his public speaking cues from Ryan Seacrest. Get the promotional plug in, then pause after every word for dramatic emphasis: “Will…You…Marry…………………..[audience: oh my god, marry who? Who is he going to say? WHO?!?!]…….ME?”

    • Morgan (The818)

      OMG, you are SO EFFING RIGHT.

  • http://twitter.com/ElwoodJBlues Todd Jones

    When did Diana Degarmo turn 45? Seriously. She looks WRECKED.

    • Snarky_Amber

      She always wore too much makeup and dressed too old for her age, though. I remember when she was a contestant on AI I would always remark on how she looked 16 going on 45.

  • Alena

    Ha ha ha ::awkward turtle::

  • http://www.sweetney.com Sweetney

    Oh god, I hadn’t seen the pic with Tori’s boobies… ugh. TWITTER FAIL AHOY.

  • Tyskkvinna

    In his defense, if some major jeweler offered me a bucket of bling if I meant I embarrassed myself during the proposal, I’d be all of that. If nothing else, it’s a great story in 20 years.

  • http://harpershappenings.com Mandy

    Ok so I’d never seen the Tori Spelling thing and I just died. Also, reliving some of these, especially the A Simp one, is also killing me from second hand embarrassment. Good god.

  • SuzyQuzey

    Good lord, pass the fucking eye bleach, STAT.

  • http://diefrau.blogspot.in/ die Frau

    I didn’t see the proposal, so please tell me: Did he go to Jared?

    I could have resisted, but I didn’t.

    I kind of loved it that the movie The Rocker referenced Ashlee Simpson when Vesuvius had a lip-synching meltdown on stage.

  • MDub2000

    I don’t watch AI, and I wish I could go back in time to when I’d never seen that proposal. I also want to cut dude’s hair because WTF IS THAT?