I owned this book, by the way.

I owned this book, by the way.

My first big crush on a human* was Leonardo DiCaprio. I cried for him in Growing Pains, clutched my heart for him in What’s Eating Gilbert Grape?, shook by fist at Robert DeNiro for him in This Boy’s Life, and, of course, thought about him in the bathtub after Titanic. While he has inexplicably maintained the appearance of a 19-year-old his entire life, today is actually his 40th birthday, so there’s no better time to take a Leo Strut down memory lane and smugly toast everything about his hottest years.

Now, I’m by no means saying Leo isn’t a ridiculously attractive person still; dude’s still hot, he’s just kind of skeezy and impersonable nowadays, as is so often the case with famous guys who exclusively date 21-year-olds despite getting older and older.

(Related: A Comprehensive Guide To Every Model Who’s Let Leonardo DiCaprio Into Her Vagina)

Even if you still dig Leo like the permanently good looking fellow that he is, it’s hard to deny that there were some serious glory days, particularly when it comes to how those of us who grew up in the 90s look at Mr. DiCaprio. Let’s relive all those heart flutters now with each iteration of Hot Leo, shall we?

Growing Pains Leo (1991 – 1992)

Mike-Seaver-and-Luke-growing-pains-leonardo-dicaprioTechnically, I was 2 years old when a 17-year-old Leo made his Growing Pains debut as Mike Seaver’s troubled student Luke, but toddler Sam already knew what was up: this guy was total soulmate material. I still remember crying about Luke’s broken home storyline after he dumped all the bottles of alcohol out and the Seavers were like “that kid is troubleeee!” but then it comes out that his parents were alcoholics and he just didn’t want the same for the Seavers, and we were all like “omg, real growing pains.” Unfortunately, Mike Seaver/Kirk Cameron turned out to be a homophobic sexist, but at least Leo’s career was launched!

This Boy’s Life Leo (1993)

leonardo dicaprio this boy's lifeI distinctly remember crying to this movie when I was little as it played on TV at the hotel my family was staying in during some summer vacation. It’s so good, but so sad, though it was definitely a solid sign for Leonardo DiCaprio’s future considering how insanely powerful his performance was. If movie trivia serves my memory correctly, he actually missed his own high school graduation to film This Boy’s Life–early dedication, man.

The Basketball Diaries Leo (1995)

leonardo dicaprio the basketball diariesSo troubled, so sweaty, so squinty. So Leo.

Romeo + Juliet Leo (1996)

Leonardo DiCaprio Romeo + Juliet smoking bleeding and being hotThis particular Leo deserves multiple screengrabs because in my opinion, this was Leo at peak hotness. The following Leo is always a favorite, too, but Romeo + Juliet Leo was romantic, mysterious, and walking through the desert to “Talk Show Host” like the 90s stun gun he was. The file name for the above image is literally “Leonardo DiCaprio Romeo + Juliet smoking bleeding and being hot,” by the way.

*I was really into Captain Planet, but I’m not really sure if that counts because he was a super hero and also a 2-dimensional cartoon.

Click to the next page to see the most romantic, the least romantic, and the most crown-filled roles Leo’s ever played, as well as sing along to a tribute.

Titanic Leo (1997)

titanic jack dawson leonardo dicaprioYOU JUMP, I JUMP, REMEMBER?

The Man In The Iron Mask Leo (1998)

leonardo dicaprio man in the iron maskWhat joy I felt upon realizing we were to see not one, but two Leos! Sure, one was a murderous sociopath with a laurel crown, b-b-but two Leos!

The Beach Leo (2000)

Leonardo-Dicaprio-The-Beach-2-PortableThis movie was pretty awful, sure, but it also featured enough shirtless Leonardo DiCaprio to burst a convent into lusty flames. Or just enough to actually make it commercially successful despite no critic thinking it was worth seeing.

Catch Me If You Can Leo (2002)

catch me if you can leonardo dicaprioHe can fly a plane and lie ridiculously well? Definitely appealing in entirely too many ways, including some fairly unhealthy ones, but whatever, this was 2002 and we were all crazy anyway.

Gangs Of New York Leo (2002)

amsterdam-vallon-gangs-of-new-york-leonardo-dicaprioHe was rugged and ragged, but most of all, he had great hair. He always has great hair.

And then came The Aviator and The Departed, wherein Leo became more stressful to watch than anything, and by the time we reached Shutter Island, Hot Leo’s days were all over. So, at the risk of embarrassing myself, I’ll share this little detail of Young Sam’s life: I literally used to play “My Heart Will Go On” on my flute at night and hope that someday, I would meet my Jack Dawson. Yes, really. And now…our hearts must move on from Leonardo DiCaprio.


We’ll miss you, buddy.