In December 1997, I went to the movies with my friend Mel and decided to check out this film called Titanic. At the time, it was slowly building buzz, and since we were 12 years old, we had nothing but free time on a Saturday afternoon. Turns out that viewing of Titanic turned into the first (of five) times I’d see the film, and an obsession with the film and Leo took over my life.

I was the epitome of Titanic fan girl. I cut out every single Titanic ad from the newspaper and taped it on my wall. I somehow had the script and would watch along with my VHS tapes. I then proceeded to make a checklist of Leo movies I needed to see, and thus began my sub-obsession with Mr. DiCaprio. Luckily, he turned out to actually be a great actor, not just another teen heartthrob that would come and go (looking at you, JTT).

So in honor of The Great Gatsby coming out today, here’s a look back at some of my favorite Leo performances from over the years, proving that just like a fine wine, he just gets better with age. And also, it’s a damn shame he hasn’t won an Oscar yet.

What’s Eating Gilbert Grape (1993)

*Spoiler in the video!*
A young Johnny Depp plays the title character who has to care for his mentally challenged younger brother, played by Leo. It’s crazy how Leo just transforms into this character, and at just 19 he got his first Academy Award and Golden Globe noms.

The Basketball Diaries (1995)

Looking back, my parents probs shouldn’t have let me buy this movie because it’s not reallly about basketball like the title sounds. Leo plays a teen drug addict, and I’m pretty sure I’m still scarred from watching it as a 12 year old.

Romeo + Juliet (1996)

Do this day, this is still one of my absolute favorite Leo movies. Everything about this adaptation was spot on, and actually made an old Shakespeare play fresh, new, and relevant. The California setting combined with the excellent soundtrack is something that only Baz Luhrmann could pull off, which is yet another reason why I cannot wait to see The Great Gatsby.

Titanic (1997)

Titanic is a story of… are you kidding me if you don’t know what Titanic is about or haven’t seen the movie you shouldn’t even be reading this right now. GTFO. Here’s a deleted scene from the movie, instead!

Catch Me If You Can (2002)

Tom Hanks chasing Leo around the country? Yes. Sign me up.

The Aviator (2004)

Leo played the insane Howard Hughes in this film, and don’t get me wrong, he was amazing and all, but I watched this movie in the theater. I couldn’t believe how long it was. 169 minutes aka almost 3 hours, which to be fair, is shorter than Titanic. HOWEVER, i was not expected it to be that long and I couldn’t get my mind off anything else but getting out of the theater.

The Departed (2006)

Next to The Town, this is one of the greatest Boston films ever, and like anything Leo does, he puts on the Boston accent with ease, without overdoing it like a lot of actors tend to do. Plus how can you go wrong with Matty D, Marky Mark and Jack all in one film?

Revolutionary Road (2008)

This movie is not a happy one. Like Titanic with all its sinking into the ocean, was a comedy compared to Revolutionary Road. As amazing as it was to see Leo and Kate back together, it was still a really depressing film, so here’s a clip of Kate professing her love to Leo when she won the Golden Globe in 2009.

Shutter Island (2010)

So how much of a mind fuck was this film? Leo went back to good old Beantown for this movie, which was based on a great Dennis Lehane novel. Any time there’s a psychiatric ward involved, I know I’m going to be a little freaked out. This was no exception.

Inception (2010)

Speaking of mind fucks… Just when Leo messes with your head in Shutter Island, he does it again with Inception. Except like 10 times worse. I remember having to just sit in the theater for a good 2 minutes without moving while the credits rolled to figure out what happened. I still don’t think I know exactly what happened, and I’ve seen it like 3 times. DREAMS ON DREAMS ON DREAMS, Y’ALL!