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.