December 15, 2017

Top 10 Most Embarrassing Celebrity Yearbook Photos

Most Embarrassing Celebrity Yearbook Photos!

Most all of us have had a funny or embarrassing yearbook photo at least once in our school years. But, when you’re a celebrity, having an embarrassing image – or one that is counter-intuitive from your desired persona – is particularly difficult to deal with. Below we have our selections for the 10 Most Embarrassing Celebrity Yearbook Photos. Enjoy!

10. Snoop Dogg

Snoop Dogg embarrassing yearbook photo

Not that this is a “bad” photo, but this upstanding, scholarly-looking image is certainly a far cry from the thug life, weed smoking reputation that Snoop has worked so hard to build.

9. Jennifer Love Hewitt

Jennifer Love Hewitt embarrassing yearbook photo

Ah, Jennifer Love Hewitt… I almost hate posting this here, as I’m a huge fan. But, it is a very funny yearbook photo and it really looks nothing like the curvy bombshell that she is today, so here it is anyway.

8. Kristen Stewart

Kristen Steward embarrassing yearbook photo

The Twilight star was a pretty good looking young man, wasn’t she?

7. Avril Lavigne

Avril Lavigne embarrassing yearbook photo

This yearbook photo of Avril Lavigne is a polar opposite of the rocker’s persona today.

6. Halle Berry

Halle Berry embarrassing yearbook photos

It looks to me that Halle has maybe had a little bit of “work” done since her high school days??

5. Eminem

Eminem embarrassing yearbook photo

Does this look like a troubled kid with no friends? Eminem is famous for rapping about problems in his childhood days, but I don’t get that when I look at this yearbook photo.

4. Kate Gosselin

Kate Gosselin

Kate Gosselin is one celebrity (if you can call her that) that has admittedly had plastic surgery procedures. I, for one, think it was a big improvement!

3. Madonna

Madonna embarrassing yearbook photo

Madonna may have actually “been” a virgin when this yearbook photo was taken!

2. Lil Jon

Lil Jon embarrassing celebrity photo

What can you really say about this yearbook photo of Lil Jon? He’s certainly gone out of his way to change his look / image, that’s for sure.

1. Ryan Seacrest

Ryan Seacrest embarrassing celebrity yearbook photos
Ryan Seacrest. Wow. Was this really you as a boy? You’ve come a long way, my friend. Good for you.



  1. Just amazy changes. i can’t believe that these are really their pictures in their childhood. Great changes 😉

  2. Never seen these before, great!

  3. hahaha jennifer love hewitt looks like anne frank

  4. That is not a yearbook photo of lil’ Jon. Check your research.

  5. Notice how Ryan Seacrest’s eyes went from brown to green. LOL.

  6. Ryan Seacrest?



  7. I have no idea why madonna made it to your list…

    • While she looks good in the photo, it made our list because it is such a far cry from the “bad girl” image that Madonna worked so hard to create.

      Thank you for visiting and commenting on!!

  8. Mathew lewis should be on here…

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