1996: Leonardo achieved heartthrob and leading man status with the release
of, Romeo + Juliet, which pulled in $147 million at the box office.
Unfortunately, he had a little crutch that year. We can’t say we were crazy
about his shiny green shirt, but hey, it was the nineties!

1997: Leonardo was dressed to impress at the Los Angeles premiere of
Titanic, well suited for the boat-based masterpiece in navy blue. The star
had no idea the award-winning film would go onto be the highest-grossing
film of its time, taking in over $1.8 billion.

1998: At the Golden Globe Awards with his costar Kate Winslett, Leo still
looked like a little boy in a black tuxedo.

1998: Leo with French actor Gerard Depardieu at the Parisian premiere of The
Man in the Iron Mask, looked sophisticated in a black suit.

1999: Leo dated model Kristen Zang on-and-off through the 1990’s, who joined
him at Magic Mountain for a celebrity charity event. The two were clad in
dressed down duds.

2000: Once again starring in a film based around the ocean, Leo rocked an
all navy blue ensemble to the Los Angeles premiere of The Beach.

2003: Leo bulked up and sported some facial fuzz to the UK premiere of Gangs
of New York.

2004: Leo was very involved in John Kerry’s presidential campaign. Not only
did he contribute financially and campaign for the politician, but he also
rocked his shirt to a premiere in NYC.

2004: Leo, accompanied by costar Cate Blanchett and one of his biggest fans
(and employers!) Martin Scorsese, looked devastatingly dapper in a black
suit at the NYC premiere of The Aviator.

2004: Leo had a grey day at the London premiere of The Aviator, looking
super GQ in his perfectly tailored suit.

2005: Leo’s Brazilian supermodel girlfriend Gisele Bundchen escorted the
actor to the Academy Award, where his was nominated for his portrayal of
Howard Hughes in The Aviator.

2006: Leo rocked a sassy striped tie to the Rome Film Festival premiere of
The Departed, where he was flocked by Martin Scorsese and Vera Farmiga.

2007: At the Critics Choice Awards, Leonardo looked dapper in black.

2007: At the Cannes Film Festival screening of the 11th Hour, the
environmentally aware actor looked super hunky in black.

2008: Leo reunited with Kate Winslet for Revolutionary Road, looking all
grown up eleven years after he walked the carpet with her for Titanic.

2009: The dynamic onscreen duo got all dressed up for The Golden Globes,
where Leo was nominated for Best Actor.

2010: Not a young boy anymore, Leo walked the red carpet of the London
premiere of Inception, wearing a gorgeously grey suit.

1990: Leo scored his first role on the television show Parenthood. The blonde child actor was ready for super stardom from the start.

1990′s: The sporty child actor loved having his picture taken.

1992: At MTV’s Rock n’ Jock Basketball Tournament, Leo sported a jersey.

1995: With Mark Wahlberg, the Basketball Diaries star dressed up for the red carpet.