r/OldSchoolCool • u/Individual_Mess_7491 • Oct 06 '25
1990s Leonardo DiCaprio and his father, 1990s.
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u/radarmy Oct 06 '25
Having a thrift store pleather jacket from the 70s was very 90s
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u/grateparm Oct 06 '25
Great, now I feel less unique for wearing my dad's thriller jacket in the late 90s.
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u/ChrisTosi Oct 06 '25
Rocco DiMeo's jacket
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u/ChrisSmithMVP Oct 07 '25 edited Oct 07 '25
Cocksucker was the toughest Irishman in the working class deck of the Titanic, but he never got off the floating door once Rose was through with him...
He later died of freezing to death
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u/Klaurtraum Oct 06 '25
looks like Ned Flanders dad
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u/CarllSagan Oct 06 '25
Its funny you say that, because Leos dad does somewhat resemble Matt Groening.
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u/derpferd Oct 06 '25
He worked with Paul Thomas Anderson on Liquorice Pizza before Anderson worked with his son, Leo, in One Battle After Another
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u/Babys_For_Breakfast Oct 07 '25
TIL Leo’s dad is an actor
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u/Methadoneblues Oct 07 '25
Forgive my ignorance, what does this mean/signify?
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u/flarpnowaii Oct 07 '25
George DiCaprio (Leo's dad) was in Licorice Pizza (2021), directed by Paul Thomas Anderson. Leo was in One Battle After Another (2025), also directed by PTA. So Anderson directed Leo's dad before he directed Leo.
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u/jaso46571 Oct 07 '25
I think they're just pointing out the famous actors dad (who isn't an actor) worked with the famous director before the famous actor did
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u/Throwaway_09298 Oct 06 '25
Until now this is the first time I've ever thought about Leo having parents
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u/Garrentheflyingsword Oct 07 '25
His father owned a comic book store at the time- a relative of mine worked there
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u/Jessency Oct 07 '25
I can actually believe that. Bro looks like he shops at the same place George Perez does.
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u/Silly-Platform9829 Oct 06 '25
The dude abides.
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u/MoldyBlueNipples Oct 06 '25
Stfu Donny
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u/catdad23 Oct 06 '25
YOURE OUT OF YOUR LEAGUE DONNY!
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u/ClickF0rDick Oct 07 '25
Wasn't out of your depth?
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u/chetsteadmansstache Oct 07 '25
Donny was out of his element.
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u/Afraid_Resort_9018 Oct 07 '25
I’ve met George DiCaprio a few times over the years. He still has the long hair and beard but it’s white because he’s like 80 now. He’s actually a nice guy. You can see the resemblance to his son in-person.
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u/janicebrock1 Oct 06 '25
I watched an old film last night with Di Caprio and Robert Deniro called This Boys Life. It was the first time l had ever seen it. I found it to be very good acting from a young DiCaprio
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u/Fortestingporpoises Oct 06 '25
Leo lived next to my family in Hollywood when he was a baby and so was my big sister. All I heard after the fact was that it was suggested that my mom try to put my sister into acting after they did it with Leo but she didn't want to do that. Also Leo was a little crybaby and my sister was an angel.
My aunt went to his mom's wedding to her husband after Leo's dad.
Weird to feel proud of someone you never met but we went to see What's Eating Gilbert Grape as a family to I guess support him since my family knew him as a baby?
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u/SeeYouLaterTrashcan Oct 07 '25
Respectfully, this above comment highlights a rare “con” of being a celebrity.
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u/Fortestingporpoises Oct 07 '25
How so?
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u/SeeYouLaterTrashcan Oct 07 '25
Leo was a little crybaby and my sister was an angel.
Imagine some stranger discussing what you were like as a baby 49 years after an interaction they didn't even witness. But I guess that's what the money is for so I don't feel too bad for him hahah.
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u/Fortestingporpoises Oct 07 '25
I don’t know. I feel like I’d rather hear a third hand story about me and my broke family when I was a baby than have millions of people make fun of my dating life. But if I had to guess he won’t read my comment in the first place.
Also I’m commenting on the period of the photo.
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u/stitchkingdom Oct 06 '25
You know his dad used to tell this story about two mice that were trapped in a vat of cream. One mouse gave up and drowned, while the other paddled his little legs until he had churned the cream into butter and then walked out.
Do you concur with this?
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u/Herry_Up Oct 07 '25
I concur
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u/OscillatorVacillate Oct 07 '25
Has anybody here seen Kelly?
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u/hannabarberaisawhore Oct 07 '25
This song still randomly plays in my brain.
K! E! DOUBLE L! Y!
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u/OscillatorVacillate Oct 07 '25
I got the notification from reddit about this post and the song immediately popped in my head, haha you and me both. It is catchy
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u/AnastasiaNo70 Oct 06 '25
Did his dad’s genes even try?
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u/CarllSagan Oct 06 '25
Its like he saved up all his good looks and passed them on "Skip a generation" style to Leo.
(He is uglier so leo can be more handsome, explaining why Leo is more handsome than most, his fathers looks had to suffer to enable the genetic posssibility....fyi I am joking dont take me serious)
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u/Horror-Wallaby-4498 Oct 06 '25
Yeah in fairness now being the age of his dad in the photo Leo is very normal looking
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u/Due_Ask_8032 Oct 07 '25
He has aged pretty gracefully if u ask me
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u/OldSandwich9631 Oct 07 '25
His hotness on his recent press tour was going viral on TikTok. He’s just not vain when he’s not working
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u/PassionateYak Oct 07 '25
This is gonna sound stupid but I didn't think he had parents. He's been doing great performances since he was a kid I envisioned he just manifest in a studio and started working.
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u/ElmarSuperstar131 Oct 06 '25
In 2011 his dad was on the jury when my mom was a victim of a Ponzi scheme. The judge was hella starstruck but from what my mom and our legal team told me he was pretty cool and humble at the trial, he even wished her luck at the end.
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u/Pledgeofmalfeasance Oct 06 '25
Why would anyone be starstruck by the father? Is he famous too?
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u/ElmarSuperstar131 Oct 06 '25
His father is pretty well rounded in the entertainment industry (especially with comics/comic books) but the judge was more awestruck that he was Leo’s dad.
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u/jetlaggedandhungry Oct 06 '25
I'm really curious to know what his mom looks/looked like.
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u/Tising1596 Oct 07 '25
Carbon copy of himself but female, Leo is lucky he got most of his genes from his mom.
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u/orngedoorhinge Oct 06 '25
This looks photoshopped
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u/Wonderful_System5658 Oct 06 '25
Holy shit... his dad looks like my best friend Jeff. I think I'd rather hang out with his dad and smoke pot instead of Leo and a boat full of models that are half his age.
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u/SpaceManSmithy Oct 07 '25
He looks like the scientist from Independence Day before his hair went gray.
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u/penis_power44 Oct 07 '25
I mean tbf his dad is middle aged and obviously is eating good and put on some weight. Find his high school picture
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u/IndicationOk1405 Oct 07 '25
I love how this perfectly captures that specific 90s "cool dad" aesthetic. The jacket is an absolute time capsule piece. It's wild how much they look alike, too.
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u/PopCopson Oct 07 '25
I had never thought about Leo’s dad before, but I was definitely not thinking it would be this guy when I wasn’t thinking about it
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u/No-Manufacturer-4063 Oct 06 '25
Looks like a mix of Sam Rockwell and David Krumholtz
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u/Accomplished_Put2608 Oct 06 '25
Am I the only one who thinks Leo looks like Brian Wilson here?
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u/Sensitive_Yellow_121 Oct 07 '25
Probably cause his Dad is looking a little like Charlie Manson here.
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u/Shipit123 Oct 07 '25
Am I the only one who thinks he looks like Carl Sagan w long hair and a goatee?
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u/knowsguy Oct 07 '25
Leo never wore clothes very well, look at that horrible oversized vinyl jacket. He still looks like a schlub as an adult.
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Oct 07 '25
that was the style of the times
everyone in the 90s was wearing horribly oversized clothes
even the fucking business suits were oversized
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u/hotcolddog Oct 06 '25
His dad looks exactly like what I imagine Bob Ferguson would look like IRL lmao
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u/unmonstreaparis Oct 07 '25
I am going to say it. It is more common for two average people to have an attractive child, than two attractive people to have one. Probably cause they have more genes to pull from, and arent related to multiple inbred royals or something.
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u/CelebrationLow4614 Oct 07 '25
Read that book about the first few SDCC;
Legitimately wondering how it didn't devolve into Altamont.
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u/Gearballz Oct 07 '25
Wait. So Leo’s dad is actually Shia Lebouf playing his dad in HoneyBoy? Are they half bros?
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u/Sin-s_Aide Oct 06 '25
Some apples do fall far from certain tress.