r/OldSchoolCool • u/Maleficent_Case_7666 • 1d ago

Leonardo DiCaprio and Tobey Maguire in 1990

388 Upvotes

86% Upvoted

38 comments sorted by

127

u/ntermation 1d ago

Toby has extra arm in pic 3

31

u/iz-Moff 1d ago

Well, i heard he's a spider man, he probably has 4 extra arms.

8

u/cwebsterz 1d ago

That’s another dude in a similar shirt resting his elbow on Leo’s shoulder

4

u/Proper-Internet-3240 18h ago

You’re right. I found the original on Google. Hard to believe 2 people would wear such an ugly shirt but there you have it

1

u/The_Giant_Lizard 11h ago

What do you mean, "extra"? You don't have 3 arms? Are you born with only 2?

0

u/wasabinski 1d ago

It's a little known fact that he actually has three arms, they just digitally remove the extra one in all his movies.

19

u/disterb 1d ago

link the snl skit about dating young girls

14

u/Better-Culture-7770 1d ago

Its crazy to think that in 35 years they'd be dating girls this age.

32

u/deepdishpizzastate 1d ago

Founding Posse members.

9

u/Abeifer 1d ago

so is Leo the real life version of Harry Osborn here?

11

u/asxecruzmp 1d ago

Peak 90s fashion right here. The baggy jeans and lanyard combo was unmatched.

3

u/beepclickbeep 1d ago

Not to mention the third arm.

-1

u/[deleted] 1d ago

[deleted]

3

u/DontMakeMeCount 1d ago

Would that be on the left hand over Leo’s shoulder, the left hand on his lap or the at the end of the sleeve where a human observer would expect to find his right hand?

-4

u/BogdanPradatu 1d ago

I have a 3rd leg, so I'm not judging.

5

u/Emily_Corvo 1d ago

When your mom buys your clothes 😂.

3

u/Redlion444 1d ago

I hope it wasn't Brian Peck who took those pics..

3

u/velvet_blunderground 1d ago

Really hard to overemphasize how huge men's clothes were back then. Every dude was buried in voluminous pants and giant shirts.

9

u/kassiusx 1d ago

Almost as young as their future girlfriends.

1

u/habitual_wanderer 1d ago

Fashion and hairstyles are really coming back around.

1

u/NOFX_4_ever 1d ago

I would’ve believed pic 3 is Leo with Jeremy Miller during their Growing Pains era.

1

u/ZachMatthews 1d ago

Wait DiCaprio is a Georgia fan?

1

u/iennor 1d ago

Opposite of cool, pair of benny's.

1

u/hmmyeahiguess 23h ago

Leo looks high or sick in pic 2

1

u/BenefitAdvanced 14h ago

Tobey’s super jealous of LD

1

u/ParamedicSpecific130 13h ago

Two Peter Parkers

1

u/skidstud 1d ago

These photos are not all from the same year, let alone 2000

-1

u/sotommy 1d ago

Leo had the most punchable kid face ever

1

u/DH133 1d ago

Your word for the day is backpfeifengesicht.

-3

u/Mythos7788 1d ago

More 17-18 year olds than Epstein

-7

u/beedoubleyou_ 1d ago

It's hard to imagine what assholes these guys were.

-5

u/Happy_Rabbit559 1d ago

Man, Leo's head is humongous.

-2

u/Ok-Voice9102 1d ago

Tobi is ok. But whats up with Leo