Pop Culture | Celebrities | 90s

15 Teen Magazine Photo Shoots That Prove Leonardo DiCaprio Was The King Of The 90s

Leonardo DiCaprio is one of the biggest A-List stars in Hollywood. He's made so many classic movies, he's had so many iconic characters, and his career has been a non-stop hit-machine ever since we first met him.

DiCaprio first came onto the screen all the way back in the 80s, appearing on a game show called Fun House, before becoming one of the regulars on Romper Room.

He got his first movie role in Critters 3, and shortly after he was cast as Luke Brower in Growing Pains.

Growing Pains
ABC

Once he was a regular on that show, his whole life seemed to change drastically. He became one of the most beloved stars in Hollywood, and every preteen girl had his pictures on her wall.

As his career continued on, he took more impressive roles but still the girls were swooning. Because it was the 90s, teen magazines were the most important thing for every star to do if they wanted to keep their names out there.

However, what this means is that even fairly serious actors like Mr. Leo DiCaprio have a bunch of old pictures that are a little bit embarrassing. Probably the biggest downside to growing up on camera is the fact that you have photographic evidence of every awkward moment.

Leo's pictures tell a story though, let's see what all these glorious images say.

1. When he really had to think about his choices

Leonardo Dicaprio
BOP

You know he's just sitting there wondering, "Does this hair gel make my hair look cool and rebellious? Or greasy and kind of like a mess?"

The truth is Leo, you can manage to look a little bit greasy, but still very cool. You've just got it all!

2. When he was really thoughtful

Leonardo DiCaprio
All-Stars

This Leo is thinking, "If I look like this, then they will know I am a super serious actor who wants to win an Oscar one day. Does this weird plant thing make me look cool?"

Well, guess what Leo, you do look cool. Okay, you don't look that cool, but you don't look insane.

3. When he waved at us without shoes on

Leonardo Dicaprio
Teen Beat

Leo, Leo, Leo... He's probably sitting there thinking "Oh hey you were the photographer last time nice to *CLICK* wait, was the the picture? Was that it?"

Look, it's not his fault, but whoever styled him without shoes made a bad choice.

4. When his milkshake didn't bring the boys to the yard and he was upset about it

Leonardo Dicaprio
Big Bopper

The song made a promise that it couldn't deliver on. He's sitting there thinking "I guess I'll just drink this all alone then..." while looking into the middle distance, brokenhearted and alone.

Someone give Leo a hug please.

5. When Leo was very small

Leonardo Dicaprio
Big Bopper

He was the smallest little thing, and he was just getting started, but he looks like he can see the future. "I'm going to be a big star, and yet they still won't give me an Oscar for another 20 years... Silly fools."

Oh Leo, so much wisdom in those eyes.

6. When Leo went for a weird grundge-prep combo look

Leonardo DiCaprio
Teen Beat

He look like that one preppy kid who just discovered Nirvana so he's starting to let his hair grow out, and now buys plaid shirts instead of regular button ups. He's not quite up to snuff yet, but he'll get there.

7. When he had a rare happy photo

Leonardo DiCaprio
BB

Most of his pictures seem to be so serious, it's nice to see a simple smile. Although it feels like he's thinking "I see you magazine name, and believe me, I will survive these awkward photo shoots and I will become something more. Just you wait."

And you did Leo. You survived and look at you now!

8. When Leo was confused about why you didn't know who he was yet

Leonardo DiCaprio
Teen Beat

"You may not know me yet, but I guarantee one day you will. Believe me."

He's got the whole world in the palm of his hands, and he's looking pretty confident.

9. When Leo got pensive... again

Leonardo DiCaprio
Superstars

"Seriously, I'm going to be so rich, what should I do with my time? How do I get them to take me seriously as an actor? I don't want to keep doing these crazy photo shoots..."

He really does have a lot to think about...

10. When it was real sunny but his hair gel was perfect for the 90s

Leonardo DiCaprio
Superteen

"Why are they making me stare into the sun? It's so bright? Also, I have on two different t-shirts, and a flannel, and I think I am sweating more than is safe for human to sweat..."

It's too sunny young Leo, I hope you have your SPF on!

11. When he went for the spikey hairstyle look

Leonardo DiCaprio
SuperTeen

Remember when spiking the front of your hair was all the rage? Well, Leo was ready to embrace the change and tried it out. He spent years with the slicked back look, but now his hair was straight up.

However, you can see the look in his eyes that says "I know this isn't working..."

12. When he pouted about his mushroom cut

Leonardo DiCaprio
Teen Beat

He doesn't like when his hair is all fluffy, you can tell by that look in his eyes. "Just because Jonathon Taylor Thomas can rock a mushroom cut doesn't mean everyone should. Jeez."

13. When he left an award show after party too late and went straight to a photo shoot

Leonardo DiCaprio
Super Teen

"I was at the Oscars after party talking to Robin Williams and Tom Hanks four hours ago, yes please get me a coffee. Wait, make that three coffees."

At least his day-old suit look works?

14. When he looked like he was pleading for help

Leonardo Dicaprio
Tutti

"Please, I'm very young and they keep asking me to try and look cuter. HELP."

He just looks so afraid, and I feel like it's because the photographer is probably being weird. Adults telling teens to try and look cute is just not the greatest.

15. When he tried to hide that necklace but we caught it

Leonardo DiCaprio
BOP

He's got that super cool 90s necklace hiding just below the surface, but I can see it.

"If I stand like this, no one will see my strange necklace right?" I saw it. I caught you.

Which 90s Leo was on your wall as a kid?

Obviously Leo is now a huge star, but some of his photos are a little funnier than others.

He's not the only star to have their childhood photographed. A bunch of other stars have revealed what they looked like as kids and it's pretty adorable.

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