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Leonardo Dicaprio and Tobey macguire when they were teens

Leonardo DiCaprio With Tobey Maguire and Orlando Bloom 2017

Leonardo DiCaprio and Tobey Maguire

The Bromance: Leonardo DiCaprio and Tobey Maguire

Leonardo DiCaprio, Orlando Bloom, & Tobey Maguire Hang Out in New York City!

Tobey Maguire and Leonardo DiCaprio

Leonardo DiCaprio and Tobey Maguire Hang Out With Orlando Bloom

Here come the boys! The Oscar-winning actor, 42, has been building

Leonardo Di Caprio and Tobey Maguire, friends for 30 years now, met for a dinner date with their families.

Tobey Maguire Steps Out After Catching Up With Leonardo DiCaprio & Orlando Bloom

Leonardo DiCaprio and Tobey Maguire Enjoy a Yachting Trip Together

Leonardo DiCaprio, Orlando Bloom, and Tobey Maguire Stroll Through the East Village | InStyle.com

Leonardo DiCaprio, Tobey Maguire, Tom Hardy Team for Anti-Poaching Movie at Warner Bros. (Exclusive)

Recently separated Tobey Maguire is reportedly dealing with heartbreak like a mature adult: by clubbing with his old pal Leo DiCaprio and chatting up ...

Leonardo DiCaprio, Orlando Bloom and Tobey Maguire are the ultimate boys club as they enjoy a lads day out - Mirror Online

Leonardo DiCaprio has proved inseparable from his

Leonardo DiCaprio, Leo DiCaprio, Tobey Maguire

Elle

Leonardo DiCaprio, Tobey Maguire and Orlando Bloom meet up and hang out as they went

leonardo dicaprio tobey maguire

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Ladies men: Leonardo DiCaprio and Tobey Maguire are pictured out in New York on Monday

Leonardo DiCaprio Tobey Maguire

Tobey Maguire Steps Out After Catching Up With Leonardo DiCaprio & Orlando Bloom

Vivien Killilea/Getty Images Maguire and DiCaprio. Leonardo Dicaprio

Christopher Pettiet (24) childhood friend w/t Tobey Maguire & Leonardo DiCaprio

MARTHA NOBLE/GLOBE

Leonardo DiCaprio Cares for Tobey Maguire's Daughter Ruby!

Leonardo DiCaprio, Orlando Bloom, & Tobey Maguire Hang Out in New York City!

Leonardo DiCaprio Is Casually Vacationing with Nina Agdal and Tobey Maguire | GQ

View full sizeLeonardo DiCaprio, left, and Tobey McGuire pose for a portrait in promotion of their upcoming film "The Great Gatsby" in New York.

Leonardo DiCaprio, Orlando Bloom, and Tobey Maguire Take a Bro Stroll in NYC

Leonardo DiCaprio, Orlando Bloom and Tobey Maguire out in NYC, June 14, 2017

Leonardo DiCaprio, Orlando Bloom, & Tobey Maguire Hang Out in New York City!

Imagined Celebrity Connections: Leonardo DiCaprio and Tobey Maguire Plan a Night Out | Vanity Fair

Leonardo DiCaprio & Tobey Maguire - GLAAD Media Awards 2013

Leonardo Dicaprio Tobey Maguire Childhood Friends

Leonardo DiCaprio Supports Tobey Maguire's Daughter with His Best Buddies!

Leonardo DiCaprio & Toby Maguire can't talk their way into a Championship fight in Las Vegas!

The Celebrities You Forgot Used To Be BFFs

ORLANDO BLOOM & LEONARDO DICAPRIO

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Tobey Maguire: 'Cardboard' Star and Producer!

Leonardo DiCaprio & Tobey Maguire Are Good Ol' Sports At Cannes

'The Great Gatsby': Brooks Brothers Outfits Leonardo DiCaprio, Tobey Maguire

In 1995, Leo proved his serious actor credentials again with The Basketball Diaries, and did a nude scene to play Arthur Rimbaud in Total Eclipse.

Wow, so that Leonardo DiCaprio ...

Travis Barker hung out with Leonardo DiCaprio and Tobey Maguire

(Photos: Getty Images) Tom Hardy has recruited fellow Hollywood heavyweights Leonardo DiCaprio and Tobey Maguire ...

Video thumbnail for Leonardo DiCaprio Out With Tobey Maguire

Six minutes of Leonardo DiCaprio blowing a kiss to Tobey Maguire - YouTube

tobey maguire clubbing split

Leonardo DiCaprio and Tobey Maguire go shirtless for a yacht day in Ibiza: https:

Tobey Maguire and Leonardo DiCaprio Costar in The Great Gatsby | PEOPLE.com

Tom Hardy, Leonardo DiCaprio and Tobey Maquire agree to produce anti-poaching movie

Leonardo DiCaprio, Orlando Bloom, And Tobey Maguire Bro Out

Leonardo Dicaprio and Tobey Maguire

leonardo dicaprio with tobey maguire kids otis and ruby

Leonardo DiCaprio and Tobey Maguire spotted living the bachelor dream partying on a yacht

Leonardo DiCaprio and Tobey Maguire

Childhood friends Tobey Maguire and Leonardo Dicaprio. AND THEY WERE BOTH IN THE AVIATOR AND THE GREAT GATSBY HOLY CRAP

Leonardo & Tobey Maguire party like it's 1999 with… Sofia Richie?!

If you aren't familiar with Leonardo DiCaprio's infamous 'pussy posse' of the nineties, the team moniker will give you some clue as to the antics they got ...

plight don's plum

Leonardo DiCaprio and Tobey Maguire | Best Friends Forever | Best Moments

Newly Single Tobey Maguire Is Already Back in Full Pussy Posse Mode With Leonardo DiCaprio | Complex

Leonardo DiCaprio, Tobey Maguire, Lukas Haas

Amitabh Bachchan, Leonardo DiCaprio, Carey Mulligan, Tobey Maguire Opening Ceremony of The 66th Cannes Film Festival - The Great Gatsby - Premiere

Getty

Leonardo DiCaprio & Tobey Maguire, 1990

Leonardo DiCaprio & Tobey Maguire Become A 3-Way With Orlando Bloom

DiCaprio is seen with longtime pal Tobey Maguire at an L.A. Lakers game.

Tobey Maguire and Leonardo DiCaprio | Rare and beautiful celebrity photos

Tobey Maguire: I'm So Proud of Leonardo DiCaprio

Leonardo DiCaprio, Carey Mulligan and Tobey Maguire pose for pictures (Picture: Getty)

Leonardo DiCaprio and Tobey Maguire are making real estate moves on the West Coast.

Leonardo DiCaprio with Tobey Maguire & Jennifer Meyer depart 24th Annual GLAAD Media Awards

Tobey Maguire, Leonardo DiCaprio

(Image: ARIS)

In the '90s, Leonardo DiCaprio wasn't the Oscar Smiegel we know him to be today. Why, back then he was merely an attractive, talented actor who hung out ...

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Tobey Maguire just got divorced – but he's still basically married to Leonardo Dicaprio | Revelist

Catherine Martin, Elizabeth Debicki, Baz Luhrmann, Joel Edgerton, Carey Mulligan, Tobey

Leonardo DiCaprio and Tobey Maguire Party on a Yacht in St. Tropez | PEOPLE.com

Snorkel buddy.

Tobey Maguire on Working With "Best Friend" Leonardo DiCaprio in The Great Gatsby

L-R: David Blaine, Leonardo DiCaprio and Tobey Maguire (Image via Tumblr)

Over: Tobey announced on Tuesday that he's splitting from wife Jennifer Meyer after nine years

Tobey Maguire Might Be Coming For Leonardo DiCaprio's Spot As The Pussy Posse Alpha

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We haven't ...

Leonardo DiCaprio & Tobey Maguire Buddy Up at Pre-Globes Party

Leonardo DiCaprio Hangs Out With Tobey Maguire In Venice