The 26 Most Puzzling Pictures Of Leonardo DiCaprio Ever Taken

Leo, what was going on? posted on January 14, 2013 at 6:34pm EST

Matt Stopera BuzzFeed Staff posted about 4 months ago

I know, right? Now tell your friends!

The 26 Most Puzzling Pictures Of Leonardo ...

Matt Stopera

26. Was your outfit made of straw?

View this image ›

Via: dicaprio.com

25. Was it hard to sit that way?

View this image ›

Via: dicaprio.com

24. What kind of lipstick were you wearing?

View this image ›

Via: dicaprio.com

23. Why were you holding a measuring cup full of milk?

View this image ›

Via: dicaprio.com

22. Did you finish that entire measuring cup full of milk?

View this image ›

Via: dicaprio.com

21. What’s the deal with the swan?

View this image ›

Source: Annie Leibovitz / via: dicaprio.com

20. What’s happening here?

View this image ›

Source: David LaChapelle

19. How did you get your hair to stay that way?

View this image ›

Source: Interview Magazine / via: dicaprio.com

18. Did someone hit you in the face with this ice cream cone?

View this image ›

Source: Interview Magazine / via: dicaprio.com

17. What was the cross supposed to mean?

View this image ›

In other words, does this have a deeper meaning?

Via: dicaprio.com

16. Did the shell speak?

View this image ›

Source: David LaChapelle

15. Why did you knock down that chair?

View this image ›

14. Were you supposed to be holding an umbrella or something?

View this image ›

Via: ztams.com

13. Coke or Pepsi?

View this image ›

Via: ztams.com

12. Was this supposed to be sexy?

View this image ›

Via: leodicaprio.net

11. Why were you wearing a burlap sack?

View this image ›

Via: leodicaprio.net

10. What size were those pants?

View this image ›

Via: leodicaprio.net

9. What is going on with your feet?

View this image ›

That doesn’t look natural…

Via: leodicaprio.net

8. Why were you wearing a leather jacket in a water fall?

View this image ›

Via: leodicaprio.net

7. What does this mean?

View this image ›

Via: leodicaprio.net

6. What is this pose?

View this image ›

Via: leodicaprio.net

5. Where are those sunglasses now?

View this image ›

Via: leodicaprio.net

4. What was the deal with you always exposing your midriff?

View this image ›

Via: leodicaprio.net

3. Again, why did you show your belly so much?

View this image ›

Via: leodicaprio.net

2. There’s your stomach again…?

View this image ›

Via: leodicaprio.net

1. Why??!?!?!??!

View this image ›

Via: dicaprio.com

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erynbreeser The 26 Most Puzzling Pictures Of Leon... about 2 weeks ago ×
emiliea2 thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 2 weeks ago ×
haileyl thinks The 26 Most Puzzling Pictures Of Leon... is LOL & Cool Beans about 3 weeks ago ×
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michellec18 thinks The 26 Most Puzzling Pictures Of Leon... is Win & Cute about 2 months ago ×
mlissam thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 2 months ago ×
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mariasf thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
remonao thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
remonao 3 months ago

Oh no no no, I wish I had never seen these. The shell one pushed me over the edge.
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LOL WIN OMG CUTE WTF FAIL GEEKY
kestinp The 26 Most Puzzling Pictures Of Leon... and thinks it’s Win & LOL about 3 months ago ×
newmanator The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
mayrag2 The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
passingcars The 26 Most Puzzling Pictures Of Leon... and thinks it’s Cute about 3 months ago ×
lauren d. The 26 Most Puzzling Pictures Of Leon... and thinks it’s LOL about 3 months ago ×
moirat thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
adrianazarahemlaalvareze The 26 Most Puzzling Pictures Of Leon... and thinks it’s WTF, Cute & LOL about 3 months ago ×
dnt54 thinks The 26 Most Puzzling Pictures Of Leon... is Geeky, WTF & Fail about 3 months ago ×
ashieheartjoshie thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
sarahd40 3 months ago

so sexy!
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natashak6 thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
angieleed The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
danimooseya thinks The 26 Most Puzzling Pictures Of Leon... is Cute about 3 months ago ×
heidio2 The 26 Most Puzzling Pictures Of Leon... and thinks it’s Win & LOL about 3 months ago ×
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ronnic2 thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
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Kristen8 The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
saras39 thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
aluik 3 months ago

#7 Leonardo sitting on top of a generator throwing gang signs. Your argument is invalid. #19 Leonardo is a Super Saiyan your argument is invalid. #22 Leonardo drinking milk from a measuring cup in white garment. Your argument is invalid.
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LOL WIN OMG CUTE WTF FAIL GEEKY
raze The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
alyssap9 3 months ago

#5…obviously on Guy Fieri.
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phonel The 26 Most Puzzling Pictures Of Leon... and thinks it’s LOL about 3 months ago ×
nintendo64 3 months ago

Bahahaha xD
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LOL WIN OMG CUTE WTF FAIL GEEKY
emilybrooker The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
Crunchy_Sounds thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
luchan thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
hannahrufiop thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
kneebelle 3 months ago

The answer to 20 is: MAKING MY DREAMS COME TRUE.
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rachelp16 thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
barbl3 The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
ohhchlo The 26 Most Puzzling Pictures Of Leon... and thinks it’s Cute about 3 months ago ×
gabif2 The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
knappalin The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
Annacee thinks The 26 Most Puzzling Pictures Of Leon... is Trashy, Win & LOL about 3 months ago ×
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Kaylakassa The 26 Most Puzzling Pictures Of Leon... and thinks it’s LOL about 3 months ago ×
Annacee 3 months ago

Ok not trashy. I hit trashy by accident. He is the opposite of trashy.
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LOL WIN OMG CUTE WTF FAIL GEEKY
streacy The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
kathrynp 3 months ago

The Golden Age when a little stomach was about as sexy as teen mags got.
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Madison D thinks The 26 Most Puzzling Pictures Of Leon... is LOL about 3 months ago ×
llazar08 The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
sharpasabutterknife The 26 Most Puzzling Pictures Of Leon... and thinks it’s WTF & LOL about 3 months ago ×
Mandelinasue The 26 Most Puzzling Pictures Of Leon... about 3 months ago ×
Kaylakassa 3 months ago

#6 he looks like the kid who played Peter Pan
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LOL WIN OMG CUTE WTF FAIL GEEKY
Emu 3 months ago

The 90s, man.
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LynnyP 3 months ago

Soooooo glad I’m not the only one who had ALL these pics in a little collection… Leo is exactly one day older than me and we used to like all the same stuff (purely by coincidence, I promise), so obviously to my teen self this meant that we were soulmates. Maybe we would have been, had we ever met - who knows…? ;-)
And Joseph, I agree - the Leibowitz and LaChapelle shoots were some of my absolute favourites. Still are.
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LOL WIN OMG CUTE WTF FAIL GEEKY
stephalina 4 months ago

This. Inside My locker. 1998. the memories!
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noahraymondm 4 months ago

Dude. Poor DiCaprio. This shit must be really embarrassing for him now. People who exploit young people and try and turn them into stars are gross. They gave him the full One Direction treatment, with endless model shots of him in stupid poses. He doesn’t even come across as a human being. More as a product.
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LOL WIN OMG CUTE WTF FAIL GEEKY
jessicab61 4 months ago

i wish i was that ice cream cone. Also, does anyone remember the episode of ‘All That’ where they have a pinata of Kate Winslet as Rose, and beat the living shit out of it?
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LOL WIN OMG CUTE WTF FAIL GEEKY
johnmichaelw 4 months ago

Leo’s always been a great actor, even before Titanic (hell, he was nominated for an Oscar back in 1993). But I never thought he was cute until much more recently. I don’t really go for his floppy-haired, boyish look that he did in the late 90’s and the first half of the 00’s. But now, he looks fiiiiiinnnee. And he’s picking awesome movie roles.
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LOL WIN OMG CUTE WTF FAIL GEEKY
kiskanak 4 months ago

I think I prefer grown-up Leo!
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LetMeLogin 4 months ago

At least my hatred (As in can’t stand him he looks so corny) for him in his early years is justified. God wtf. lol
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anananana 4 months ago

I had the one with the swan as a poster. Lovely.
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Milly 4 months ago

This is not hot. Lol
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aeep 4 months ago

he is indeed a talented handsome man.
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LOL WIN OMG CUTE WTF FAIL GEEKY

26. Was your outfit made of straw?

25. Was it hard to sit that way?

24. What kind of lipstick were you wearing?

23. Why were you holding a measuring cup full of milk?

22. Did you finish that entire measuring cup full of milk?

21. What’s the deal with the swan?

20. What’s happening here?

19. How did you get your hair to stay that way?

18. Did someone hit you in the face with this ice cream cone?

17. What was the cross supposed to mean?

16. Did the shell speak?

15. Why did you knock down that chair?

14. Were you supposed to be holding an umbrella or something?

13. Coke or Pepsi?

12. Was this supposed to be sexy?

11. Why were you wearing a burlap sack?

10. What size were those pants?

9. What is going on with your feet?

8. Why were you wearing a leather jacket in a water fall?

7. What does this mean?

6. What is this pose?

5. Where are those sunglasses now?

4. What was the deal with you always exposing your midriff?

3. Again, why did you show your belly so much?

2. There’s your stomach again…?

1. Why??!?!?!??!

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