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A Retrospective of the Many Films Starring Both Brad Pitt and Leonardo Dicaprio Like 2 Pitts in a Dicapripod

I've Been A Film Enthusiast as Long as I can remember. I Suffer from the Same Disease Leonard did in Memento.

Brad Pitt ran over someone to get into this spot.

Brad Pitt ran over someone to get into this spot.

Once Upon a Time in Hollywood opening last July marked the 58th time stars Leonardo DiCaprio and Brad Pitt have worked together. Since the beginning of the moving image Brad and Leo have been a part of every era of filmmaking. From French Impressionism in the early 20th century to Dogme 95 to early aughties mumblecore, Brad and Leo have contributed their contribution to film history in a very contributary fashion.

Will Once Upon a Time be the final time they work together? Not likely. We thought this before right after Titanic dominated the 1998 Oscars. We thought they would stop on top. What reason would they have to work together after Titanic?

24 movies and 1 long-running TV show later, we have our answer. If Once Upon a Time is the DiCapIttrio swan song, then so be it. They owe us nothing. We owe them everything.

Your left hands need to be in your pocket.

Your left hands need to be in your pocket.

One could list every single piece of work they’ve done together, but that would take over 1,400 hours with a crew of about 75 people working around the clock in different time zones without anything to eat, maybe a cup of water to share and an online coupon to Panera.

To undertake such an endeavor is paramount to building the actual Titanic. With one arm tied behind your back. And with one shoe missing. And with your favorite grandparent in the hospital.

This list will only display a microcosm of their work together. Will this list name the consensus favorites? Of course not. That would be like naming your favorite children.

BTW- Midway through this list there will be poll ranking a random viewer’s children.

This list is but a whisper in the wind. But whispers can lead to talking in a normal voice which can lead to shouting. I’m not sure where I’m heading with this but here is a small sampling of Brad Pitt and Leonardo DiCaprio’s work together on the big screen.

No, I’m not going to expound about the time they figured out time travel as it has nothing to do with film.

Here’s the list. Keep your tissues handy.

a-retrospective-of-the-many-films-starring-brad-pitt-and-leonardo-dicaprio
CharacterActor

Jack Dawson

Leonardo DiCaprio

Rose Dewitt Bukater

Brad Pitt

Might as well get it over with because every time you think of Brad and Leo you think of Titanic. Looking back, some of the dialogue is cringeworthy and most of James Cameron’s characters are one-note caricatures (looking at you Billy Zane). But if you were in a theater in 1997 and you were lucky enough to see this on the big screen, then what you witnessed was pure movie magic. Brad and Leo were our Jack and Rose. Our heart will go on, but it still hurts like f.

Yes, we all know Jack could have fit on the plank. In a deleted scene it’s revealed that Jack is allergic to wood and if he were to be on it, he would have exploded in a giant fireball. Rose would have been incinerated in the flames.

"The version you have never seen" involves a different kind of soup. I won't spoil it.

"The version you have never seen" involves a different kind of soup. I won't spoil it.

CharacterActor

Regan

Leonardo DiCaprio

Father Merrin

Brad Pitt

Though he’s a vegan in real life, to this day Leo DiCaprio cannot look at a bowl of split pea soup without puking his guts out. DiCaprio was nominated for his first Nickelodeon Kid’s Choice Award for his role as little possessed girl Regan MacNeil in William Friedkin’s horror classic. It’s a little known fact that for his role as Father Merrill, Brad Pitt became an actual priest and performs about a dozen exorcisms a year, mostly for Matt Damon and George Clooney. The power of Brad compels you.

A selfie on a Polaroid.

A selfie on a Polaroid.

CharacterActor

Thelma

Leonardo DiCaprio

Louise

Brad Pitt

Leo and Brad blazed a trail as doomed best friends Thelma (Pitt) and Louise (DiCaprio) in Ridley Scott’s road trip classic. While playing the more sensible Louise, Leonardo DiCaprio learned that he is/was deathly afraid of cars and before every scene in the car Brad Pitt had to sing soothing lullabies so Leo wouldn’t puke his guts out. Thelma and Louise also put an up-and-coming young actor named Brad Pitt on the map as JD, one of cinema’s most memorable grifters.

a-retrospective-of-the-many-films-starring-brad-pitt-and-leonardo-dicaprio
CharacterActor

Dean Winchester

Brad Pitt

Sam Winchester

Leonardo DiCaprio

On a lark, Brad and Leo decided to do their first television show together simply because they thought it would be fun. Little did they know that playing demon fighting brothers Sam (Leo) and Dean (Brad) Winchester would last 15 seasons. While shooting an episode for season 4, Leonardo DiCaprio learned that he was allergic to demons and whenever there was a real one around, he would break out into hives. After that, the production only employed fake demons on the show. Brad Pitt actually built Baby, the show’s 1967 Chevy Impala from scratch using peanut butter and the souls of starving children.

Right here in Brainerd.

Right here in Brainerd.

CharacterActor

Gaear Grimsrud

Brad Pitt

Carl Showalter

Leonardo DiCaprio

For the chance to work with the Coen brothers, Brad and Leo took supporting roles in the 1996 Best Picture nominee and hapless but violent kidnappers Carl and Gaear. While working in the Minnesota snow Leo found out he was allergic to frozen water and now whenever he’s around it, his tongue swells and a nurse (male or female) between the ages of 56 and 63 must give him a special shot in order to reduce the swelling. After the first cast read-through, Brad Pitt suggested all the main characters have Minnesota accents since most of the movie takes place in Minnesota. During the famous woodchipper scene, Leo also found out he was allergic to being stuffed into a woodchipper so every time he gets stuffed into one, he has to take some vitamins before the next lunar eclipse.

I was in Godzilla King of the Monsters!

I was in Godzilla King of the Monsters!

CharacterActor

Elisa Esposito

Leonardo DiCaprio

Amphibian Man

Brad Pitt

20 years after Titanic, Leo and Brad brought another love story of two unlikely partners, albeit with a much happier ending this time. Guillermo Del Toro’s Oscar winning Best Picture was the first movie ever to show what Brad Pitt looks like without makeup. Brad Pitt called it his “most freeing” role. While shooting Shape, Leo DiCaprio found out he was allergic to egg timers and during one of the egg timer scenes his kidneys exploded.

Oh, THAT's why there are so many K's in the title...

Oh, THAT's why there are so many K's in the title...

CharacterActor

Ron Stallworth

Leonardo DiCaprio

Flip Zimmerman

Brad Pitt

Spike Lee’s incendiary biopic cast Leo DiCaprio as a black cop whose white partner Flip (Brad Pitt) infiltrates the Klu Klux Klan. While shooting certain scenes, Leo DiCaprio learned he was allergic to white people and whenever he’s around he starts talking about Pinterest and gluten “allergies.” Brad Pitt so enjoyed his role as a cop that he become one and is now working undercover as a…I can’t tell you that because it would compromise his life.

In Closing

There you have it. A small sampling of the work of Brad Pitt and Leonardo DiCaprio. We could put more on the list, but as we all know, Leonardo DiCaprio is allergic to any list with 8 or more items. Any exposure to said list will cause his arms to fall off. We don’t want that happening again as Brad Pitt will have to sew them on and he just ran out of string.

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© 2019 Noel Penaflor

Comments

Michael115 on August 03, 2019:

I know I would!

Noel Penaflor (author) from California on August 03, 2019:

Generations of moviegoers would pay to see that.

Michael115 on August 03, 2019:

Wow lol would have been hilarious if you found a picture of the famous bow kiss scene featuring Brad and Leo. Now that would've been perfect!