Upsetting Day: Hangin' with Leo

In 1998, if you wanted to know what Leonardo Dicaprio was up to, you could pay an adult man who stalked him ten dollars to mail you grainy VHS footage of his daily activities. That was a normal, fun thing for teen girls to do. It was distributed to the public like a regular product and not the contents of evidence bag 7.

The phrase “unauthorized documentary” is so scary because I don’t think a lot of documentaries are authorized. SeaWorld wasn’t like, “ok, I guess you can make Blackfish,” but this documentary is so close to a crime they had to let you know in the title that it’s in no way approved by Leo. Sure, we’re Hangin’ with Leo, but whatever you do– don’t tell Leo about it.

This VHS tape contains the story of 24-year-old rising star Leonardo Dicaprio, as told by some of the people closest to him: two paparazzi guys and two gossip columnists. Real adults with, I’m assuming, a lot of gambling debt to some very bad men who had no choice but to do this movie.

The gossip columnists and paparazzi are generously retitled “Celebrity Journalists” and “Celebrity Reporters.” Everyone gets a little picture of Leo next to their names with hearts coming out of his head because if the teen girls who purchase this VHS go one second without seeing Leo, they will immediately wander off to watch Chillin Outside Of Hanson’s Grandma’s Funeral instead.

"Never before has Leo's private world truly been exposed!" the VHS promises in its opening. Luckily, to this day, Leo's private world remains safe. The promises of the first five minutes of this film are never met. Instead, we get a collection of grainy, distant video clips of a humanoid figure moving through the public sidewalks of Los Angeles that could be Leonardo Dicaprio or maybe Bigfoot. No, the creature must be Leo… if you look closely at its unusual gait, only the star of Titanic could move like that.

It's Leo Dicaprio as you've never seen him before! Leo crossing the street, Leo angrily asking a man to please leave him alone, Leo running away, don't worry ladies we'll catch him! Leo can't escape. By the flashes of Papparazzar, Leo shall not go unhanged with!

The unauthorized documentary has a loose structure laid out by title cards with fonts that get progressively more and more obnoxious as the movie goes on. I like to imagine the editor started off thinking he was making an authorized documentary about Leonard Dicaprio, and when he found out that wasn't the case, he started to slack off. For instance:

We begin with charming tales of Leo's pre-fame years when he was a strange little kid who was into his pet lizard. According to celebrity journalist, Janet Charlton, Leonardo felt ostracized by the children around him, who called him "Leonardo Retardo."

I love trying to imagine where a gossip columnist would get that information. Did someone call her and say, "I was in the third grade with Leonardo Dicaprio, and here is how I used to taunt him?" Or did she send a letter to his entire third-grade class asking for any embarrassing information in exchange for a shout out in a straight-to-VHS documentary? Um, no, not the fancy authorized kind?

For sure, the saddest section of the VHS is the one about his friends that calls them The Cat Pack instead of their more popular name, The Pussy Posse. In voiceover, a celebrity journalist delicately explains, "The girls all go after Leonardo, so his friends get all the leftovers, and they're thrilled!". We watch Leonardo Dicaprio hug a bunch of models as his friends all wait off to the side, not looking particularly thrilled? Which is weird.

Then, we get into some light body shaming during the section about Leo enjoying going to the beach. This is the creepiest footage in the whole thing because it's so distant and shaky. It looks like it's being shot from behind something that pops into view every once in a while, and the main point of the segment is that it's weird how he doesn't have that great of a body, but so many girls are into him. This is where the title guy threw in the towel and invented the sarcasm font.

"He'd better be careful; all of that fun might just be going to his midsection," an adult man chuckles over footage of Leo in a swimsuit that he is not aware is being taken. He's clutching some sort of mysterious stick, probably for whacking any paparazzi that get too close. For a while after this, the energy of the video takes a weird turn where it kind of seems like it's trying to convince teenage girls who spent money on this high-quality footage of Leonardo Dicaprio they shouldn't like him.

Maybe the producers of this VHS thought there was a market in selling it to the fathers of teen girls who felt they were getting way too into Leonardo Dicaprio. It's trying to serve as a sort of teen heartthrob deprogramming material. This way, if Leonardo Dicaprio ever shows up at your house to fuck your daughter, you will be prepared.

The company that produced the video loves that picture of Leo in the hat. They even put it on the back cover of the box, which makes me even more certain this is a false flag Leonard Dicaprio disarming venture. Some poor man realized that he'd lost his little girl. His daughter would not stop watching What's Eating Gilbert Grape, and he decided this man must be stopped.

The distributor of Hangin' With Leo is a company called Real Entertainment, which is a thousand percent the name a cabal of concerned midwestern fathers who hate Leonardo Dicaprio would choose. That also explains why this VHS was mainly available for sale from the same guys who hock steaks from the trunk of their cars. They ran a special: two T-Bones and a side of guaranteed Leo repellent for your teen daughter.

The titles get increasingly sarcastic as time goes on, and even the compliments are mostly veiled insults. They call him a Renaissance man because he never went to college yet still reads books. They show a picture of him as a kid and call him a "full-faced heartthrob." Ouch! They probably had a bounty out for any footage of Leo tripping and falling, maybe getting scared and farting a little bit. These people were out for blood.

If you go into this movie as a fan of Leonardo Dicaprio, I promise you will not come out that way. In the end, you'll be saying, "Oh God, please don't tell anyone I was hangin' with Leo. That guy is such a nerd. Did you know he takes his mom to most red carpet events? I know that's supposed to be a cute, endearing fact, but somehow this movie I watched made it seem like he does it because he sucks! They said he calls her 'Mumsy'. Eww!"

Maybe that's why he can't date anyone over twenty-five? The only interested women are the ones too young to have been exposed to this VHS! Whoever got the ten dollars for putting this film together, and whatever their reasoning might have been, that money is cursed with sweaty teenage cringe. They should burn it. Some say only fifty copies of this VHS are still in circulation; others say forty-nine as they warm their hands over a fire of cackling green flames.

This article was brought to you by our fine sponsor and Hot Dog Supreme: Armando Nava, CEO of Real Entertainment Company, who will help deprogram your daughter of any hunk rated Bieber or lesser.  

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