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Sandra Hale Schulman
Special to Indian Country Today

Montana Cypress was bitten by the film bug at an early age.

Although he grew up far from Hollywood in Ochopee, a small town on the Miccosukee Indian Reservation in southern Florida, he made movies on his family’s VHS recorder and later on a digital camera.

With the primitive VHS recorder, he directed movies about “real swamp creatures like the alligators I saw everyday, and imaginary ones like Sasquatch we heard about growing up,” he told Indian Country Today recently by phone from his home in Burbank, California.

“Doing that growing up made me want to be in the film business and make movies, but you can’t do that in Ochopee,” he said.

A citizen of the Miccosukee Tribe of Indians of Florida, Cypress now is a rising star in California as a filmmaker, actor and producer, riding a wave of Native representation in Hollywood stirred by productions such as “Reservation Dogs” and “Rutherford Falls.”

He’s written, produced and acted in more than a half-dozen short films, including “Two Brothers” (2018) and “A Christmas in Ochopee” (2019). He has also written and acted in other films, including "Horizon" (2017) and “Thunderdance,” (2018), directed by Lee Cipolla.

Filmmaker Montana Cypress has written, directed and acted in more than a half-dozen films but he hasn't forgotten his roots on the Miccosukee Indian Reservation. One of his recent films, "The Transcenders," released in 2020, isset to be screened at the Lumbee Film Festival in Pembroke, North Carolina, on Sept. 18, 2021.  (Photo by Jorchual Vargas, courtesy of Montana Cypress)

A feature-length film, “The Transcenders,” released in 2020, is scheduled to be screened at the Lumbee Film Festival in Pembroke, North Carolina, on Saturday, Sept. 18. It is one of more than a dozen films directed by Indigenous filmmakers that will be featured.

Cypress also has other projects in production this year: "Raging Natives," a half-hour TV pilot for a comedy series about 1980s rockers, and "Memory Palace," a period piece. Another film, “Red Orchid,” is set to resume production this fall after work was halted in 2020 because of the pandemic.

The stories he tells are largely drawn from his early life in Florida.

“You write more about a place once you’ve moved from there,” he said.

Living on the rez

His older brother, Talbert, who helped him make the early movies, went on to become a Miccosukee tribal leader. His sister, Ashley, is a seamstress, as is his mother. His father runs a chickee business, building traditional housing from logs and palm fronds.

But Cypress realized if he really wanted to make movies, he needed to be in Southern California. So, at 27, he left Florida to attend the New York Film Academy in Los Angeles, earning an associate’s degree in fine arts in acting for film.

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He found a home at the Native Voices Theater ensemble at the Autry Museum of the American West, first acting and then writing.

“I started writing plays,” he said. “They said to write what you know, and what I knew were the unique little stories that centered from living on the rez. It was sometimes drama, sometimes it was comedy, and sometimes what I thought was serious others thought was funny. Like, in the morning I’d see the elder women feeding alligators off the dock. That to me was an everyday thing.”

He took the advice to heart.

A Christmas in Ochopee” is a light-hearted tale of cultures clashing, as a son, played by Cypress, surprises his family by bringing his white, blonde, vegan fiancée home to the Everglades for Christmas. She meets his traditional father wearing a bone choker, his hunter brother in full camouflage, and his mother who pretends to choke on a mosquito upon meeting the new member of the family.

By the time a huge 'gator head with an apple stuck in its mouth is served instead of a turkey, the laughs have flowed like water through the sawgrass.

“Two Brothers” was Cypress’s first short film in which he served as actor, writer, director and producer. Adapted from one of his plays and shot in the Everglades, the story follows two Native brothers who move from a reservation to Los Angeles.

“It has two themes,” Cypress said. “One of the brothers has a dream to be educated, and becomes an art snob. The other one wants to write stories, screenplays and novels. Comedy flows faster for me to write and I like putting in visual gags."

“Two Brothers” is currently on the playlist of Alaska Airlines flights, and will be available on YouTube later this year.

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“The Transcenders,” a full-length film released in 2020, follows the struggles of two brothers who find a remedy — “a medicine plant I made up,” Cypress says — that promises to “transform their primitive behavior” as they transition to life in the city.

His current project, “Red Orchid,” takes place in an Indian camp in the Everglades in the late 1800s.

“It’s taken in part from an old folk story,” he said. “It has a psychological horror element. It’s spooky.”

About 70 percent of the film’s dialogue will be spoken in the Seminole-Miccosukee language — Elaponke — and the cast will include some Miccosukee tribal members to be authentic, he said.

What’s ahead

Cypress is making his mark as Native representation in arts, music and film is growing. In addition to “Reservation Dogs” and “Rutherford Falls,” Native comedy is also drawing attention.

The comedy troupe the 1491s – named for the last year before Columbus arrived in America – is popular online, and a new nonfiction book, “We Had a Little Real Estate Problem,” draws from comedian Charlie Hill’s famous line.

But it took Cypress several years to connect in the Los Angeles area with the Native community, which is large but very spread out. Now 33, Cypress has since met Sterlin Harjo — the Native filmmaker behind “Reservation Dogs” — and actor Zahn McClarnon, who is Hunkpapa Lakota and Irish.

Nonetheless, he hasn’t forgotten his roots in Florida.

“My brother Montana is in a constant pursuit to find his voice and I mean that in the highest compliment,” Talbert Cypress, the Miccosukee tribal secretary, said in an email to Indian Country Today.

“He has tremendous confidence in his humor, which is something a lot of Miccosukee people fall back on,” he said. “At the same time, he is always reading and experiencing, to gain new perspective while never forgetting where he’s from. He lives on the other side of the country now but it is apparent in his work that this is his home back here and he incorporates that into his voice on screen or stage.”

Montana Cypress said he draws from both the Seminoles and the Miccosukees, and has a half-sister who is Seminole.

“On my rez you see Seminoles and on their rez you see Miccosukee,” Montana said, when asked how closely the related tribes interact and help each other.

He said the Seminole Tribe’s Everett Osceola has helped with some of his scripts, and hosted him in 2019 at the Native Reel Cinema Festival held during the annual Seminole Tribal Fair and Pow Wow.

Run by Osceola and April Kirk, the festival focuses on Seminole and Miccosukee filmmaking. The festival has screened Cypress’s films and has had him as a guest to introduce his films and appear on panels.

“We at Native Reel Cinema Fest love seeing up and coming Native/Indigenous talent hard work and have a chance to share their work on the big screen especially having a background from here in South Florida, such as Montana Cypress,” Osceola and Kirk said in an email. “Mr. Cypress's work is very versatile and also shares a style of a pure Native vision to the audience.”

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Montana Cypress films

Montana Cypress, Miccosukee Indian Tribe of Florida, has written, directed and acted in the following films:

  • "Red Orchid," in production in 2021
  • "Raging Natives," in production in 2021
  • "Memory Palace," in production in 2021
  • "The Transcenders" (2020)
  • "A Christmas in Ochopee" (2019)
  • "Two Brothers" (2018) 

Cypress has also written and acted in other short films, including:

  • "Thunderdance" (2018), directed by Lee Cipolla
  • "Horizon" (2017), directed by Lee Cipolla 
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