Brad Pitt and Leonardo DiCaprio's '90s Photos Are a True Blast From the Past

Get ready for the 2020 SAG Awards by looking back at these '90s photos of Once Upon a Time...in Hollywood stars Brad Pitt and Leonardo DiCaprio

By Elyse Dupre 17 Jan, 2020 12:00 PMTags
Watch: 26th Annual SAG Award Nominations Complete List

It's almost time for the 2020 SAG Awards—and it's going to be a big night for Brad Pitt and Leonardo DiCaprio.

Both stars are nominated for their performances in Quentin Tarantino's ninth film Once Upon a Time…in Hollywood. DiCaprio is in the running in the Outstanding Performance by a Male Actor in a Leading Role in a Motion Picture category while Pitt is up in the Outstanding Performance by a Male Actor in a Supporting Role in a Motion Picture group. They're also included in the film's Outstanding Performance by a Cast in a Motion Picture nod.

This marks DiCaprio's 11th SAG Awards nomination and Pitt's ninth. The 45-year-old actor took home the trophy in 2016 for his lead role in The Revenant while the 56-year-old actor received recognition with the rest of the Inglourious Basterds cast in 2010.

Of course, the two A-listers have spent decades working on their craft.

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Brad Pitt Spills BTS Details on "Once Upon a Time in Hollywood"

To see a few photos from their '90s days, check out the gallery.

Acting on TV

As a teenager, DiCaprio acted on TV shows like Parenthood.

Rising to Stardom

He also appeared on Growing Pains. Here he is playing Luke Brower at age 17.

Breaking Into the Industry

By 1993, he had started to secure more film roles. Here he is attending the Los Angeles screening of What's Eating Gilbert Grape at age 19.

Attending Award Shows

He also attended award shows. Here he is at the Los Angeles Film Critics Awards in 1994.

Sporting That '90s Fashion

DiCaprio kept it cool and casual with this 1994 look.

Making Movies

DiCaprio appeared in a number of 1995 films, including The Quick and the Dead and The Basketball Diaries. Here he is at the premiere for the latter.

Keeping It Cool

He also appeared in Total Eclipse that year and attended the premiere.

Shining With Shakespeare

Hey, Romeo! DiCaprio and Claire Danes attended the Hollywood premiere of their film Romeo + Juliet in 1996.

Looking Dapper

Nice tux! DiCaprio attended the royal premiere of The Man in the Iron Mask in London back in 1998.

Learning to Never Let Go

That same year, DiCaprio and Kate Winslet attended the 55th annual Golden Globe Awards. Their movie, Titanic, won Best Motion Picture (Drama) that year. While both Winslet and DiCaprio were nominated for their roles, neither took home a trophy. Winslet was also nominated for an Oscar that year; DiCaprio was not.

Sporting the Shades

Pitt hit the red carpet in a pair of blue jeans and a brown jacket for the Los Angeles premiere of the 1991 film Thelma & Louise. While Pitt had already been acting for years, many considered this his breakout role.

Entering the Spotlight

Pitt was photographed shopping at a book store in 1992. That year, he appeared in A River Runs Through It.

Suiting Up

The actor attended the National Association of Theatre Owners' ShoWest Convention in 1993.

Rocking Some Legendary Locks

Pitt let his hair down at the 1994 Legends of the Fall premiere in Beverly Hills, Calif. 

Getting Red Carpet Ready

Speaking of Legends of the Fall, the movie earned Pitt his first Golden Globes nomination. He attended the 52nd annual awards show in Beverly Hills, Calif. in 1995.

Coupling Up With Co-Stars

Pitt and Gwyneth Paltrow fell in love after co-starring in the 1995 film Se7en. They got engaged but eventually called it quits in 1997. Here they are at the premiere of the 1997 movie The Devil's Own.

Posing for the Camera

Pitt hit the Los Angeles premiere of the 1997 movie Seven Years in Tibet in style.

Meeting Joe Black

The A-lister looked dapper in his suit and tie while attending the Meet Joe Black premiere in Beverly Hills, Calif. in 1998. 

Starting a New Romance

As fans will recall, Pitt and Jennifer Aniston started dating in 1998 after being set up by their agents. They tied the knot in 2000 but divorced in 2005.

Setting the Rules of Fight Club

"The first rule of fight club is you do not talk about fight club." The second rule of fight club is...you dress up for Fight Club, which Pitt did while attending a photocall for the film at the 1999 Venice Film Festival.

Socializing With Stars

And here they both are at an event in 1995.