During the Academy Awards hosted last Sunday evening, Leonardo DiCaprio finally won his first Oscar. DiCaprio was awarded “Best Actor” for his performance in The Revenant.

It’s hard to believe that it has been nearly 2 decades since he won our hearts with his outstanding performance in the blockbuster hit Titanic. DiCaprio has come a long way since 1997, when he was just a young Hollywood heartthrob who many thought would quickly fade away from the spotlight.

Back in the late 90s, DiCaprio was the leader of an infamous group called “The Pussy Posse”, which included the likes of Tobey Maguire, David Blaine, Kevin Connolly and Harmony Korine. This group was known for partying hard and having their way with virtually any woman they wanted.

DiCaprio would go to A-List clubs just to hang out with his buddies, but other stars such as P. Diddy and Donald Trump would come over to his table and sit with him. He avoided spending money; others would buy him goodies just for the chance to spend time with him.

And all the while, he was hooking up with any woman he wanted. DiCaprio even admitted that his “hormones are just kicking in” and also said that there was not much besides sex on his mind.

The actor also had a knack for pranks. He was once known for setting off stink bombs at the ultra-high-end Sky Bar in New York. DiCaprio considered NYC to be his personal playground. In Hollywood, DiCaprio had to worry about someone in the industry catching him red-handed, but he had no such fears in the Big Apple.

DiCaprio had some run-ins with paparazzi, but his friends were always quick to defend him. In many cases, DiCaprio’s friends were willing to come in swinging to protect the actor.

It goes without saying that DiCaprio is still as big a star as ever. But he has settled down a fair bit. He’s no longer planting stink bombs or having his friends get into fights on his behalf. Still, it’s incredible to think how fast time has flown by. It wasn’t that long ago that DiCaprio was just another Hollywood hopeful. Just look at how far he has come.

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