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

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

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

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

7. Avril Lavigne

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

6. Halle Berry

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

5. Eminem

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

2. Lil Jon

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. Wow. Was this really you as a boy? You’ve come a long way, my friend. Good for you.

Celebrity Pictures

Celebrity Dresses, Celebrity Hair Styles, and More!

Everyone remembers their prom night. The excitement of the grand evening; Getting formally dressed for (possibly) the first time in your young life; Fun times with best friends; The limo ride (if you were lucky); And much more. Prom night is a favorite memory of people young and old!!
Here we have a collection of celebrities dressed up for their proms. So, reminisce about your special day / evening and enjoy seeing some of your favorite stars on theirs…

Brad Pitt and his prom date back in the 1980s. Not sure which one of these two is the prettiest!

American Idol star / country music artist Kellie Picker’s prom dress didn’t leave much to the imagination, now did it?

Britney Spears looked extremely cute in her flaming red prom dress!

Even back in the day, Fergie had all the boys’ attention.

Sandra Bullock looks almost as happy at her prom as she does now that she’s dating Ryan Reynolds.

Demi Lovato took a childhood friend to her prom.

That’s NOT the president with First Lady Michelle Obama at her Prom. (Although she IS showing an awfully lot of leg in her prom dress.)

Courtney Cox’s prom dress wasn’t all that attractive, at least not in my humble opinion. Honestly, this doesn’t look much like the beautiful Courtney Cox that we see on TV today. But, she was still very cute back then!