Movies Like The Headless Horseman

If you liked The Headless Horseman (2026), a documentary and adventure movie directed by Andy Collet, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
14 Peaks: Nothing Is Impossible (2021)
★ 7.3/10Also documentary
In 2019, Nepalese mountain climber Nirmal “Nims” Purja set out to do the unthinkable by climbing the world’s fourteen highest summits in less than seven months. (The previous record was eight years). He called the…
2
The Dawn Wall (2017)
★ 8/10Also documentary and adventure
In an unbelievable story of perseverance, free climber Tommy Caldwell and climbing partner Kevin Jorgeson attempt to scale the impossible 3000ft Dawn Wall of El Capitan.
3
The AI Doc: Or How I Became an Apocaloptimist (2026)
★ 6.9/10Also documentary
A father-to-be tries to figure out what is happening with all this AI insanity, and explores the most powerful technology humanity has ever created... and what's at stake if we get it wrong.
4
Explorer: The Last Tepui (2022)
★ 7.5/10Also documentary and adventure
This documentary starring climber Alex Honnold and famous biologist Bruce Means document their expedition to the South American sky islands in search of new species and discoveries. Follows elite climber Alex Honnold…
5
Lost on Everest (2020)
★ 7.6/10Also documentary
Reaching 29,029 feet, Mount Everest has long captivated mountaineers of all stripes. But a peak that draws athletes and mountaineers to new heights isn’t without danger — or a dark side. Perhaps the peak’s greatest…
6
Skyscraper Live (2026)
★ 7.5/10Also adventure and documentary
No ropes. No fear. Free solo legend Alex Honnold risks it all in a high-stakes, live ascent of one of the world's tallest skyscrapers in Taipei, Taiwan.
7
The Art of Flight (2011)
★ 7.8/10Also adventure and documentary
Iconic snowboarder Travis Rice and friends redefine what is possible in the mountains. Experience the highs, as new tricks are landed and new zones opened, alongside the lows, where avalanches, accidents, and…
8
Sharkwater (2006)
★ 7.6/10Also documentary
Driven by passion fed from a life-long fascination with sharks, Rob Stewart debunks historical stereotypes and media depictions of sharks as bloodthirsty, man-eating monsters and reveals the reality of sharks as…
9
Being James Bond (2021)
★ 7.8/10Also documentary
Daniel Craig candidly reflects on his 15 year adventure as James Bond. Including never-before-seen archival footage from Casino Royale to the upcoming 25th film No Time To Die, Craig shares his personal memories in…
10
Ghost Elephants (2026)
★ 7.6/10Also documentary
In Angola's mist-shrouded highlands, three KhoiSan master trackers embark on a spiritual quest to rediscover the legendary "ghost elephants" of Lisima, creatures presumed lost but remembered in ancestral trance…
11
My Mom Jayne (2025)
★ 8/10Also documentary
Through deeply personal interviews with her siblings and an examination of the photographs, letters, and belongings left behind, Mariska assembles a new portrait of her mother Jayne Mansfield, an extraordinary and…
12
Sidney (2022)
★ 6.9/10Also documentary
This revealing documentary honors the legendary Sidney Poitier—iconic actor, filmmaker, and civil rights activist. Featuring interviews with Denzel Washington, Spike Lee, Halle Berry, and more.
13
Avatar: The Deep Dive - A Special Edition of 20/20 (2022)
★ 7.2/10Also documentary
An inside look at one of the most anticipated movie sequels ever with James Cameron and cast.
14
Obi-Wan Kenobi: A Jedi's Return (2022)
★ 6.8/10Also documentary
This special explores the return of Obi-Wan Kenobi and Anakin Skywalker to the screen, as well as Ewan McGregor and Hayden Christensen to their classic roles. Director Deborah Chow leads the cast and crew as they…
15
Marvel's Behind the Mask (2021)
★ 7/10Also documentary
A documentary special that explores the power of identity behind the iconic superheroes we know and love today. These legendary Marvel creations and stories have not only reflected the world outside our window – they…
16
Hawking (2013)
★ 7.6/10Also documentary
The extraordinary story of the planet’s most famous contemporary scientist, told in his own words and by those closest to him. Made with unique access to Hawking’s private life, this is an intimate and moving journey…
17
Marvel Studios Assembled: The Making of Black Panther: Wakanda Forever (2023)
★ 6.3/10Also documentary
Follow the production of “Black Panther: Wakanda Forever” as the cast and crew take on the incredible challenge of remembering T’Challa with a chapter befitting the late king. Through intimate behind-the-scenes footage…
18
The Weather Underground (2002)
★ 6.6/10Also documentary
The remarkable story of The Weather Underground, radical activists of the 1970s, and of radical politics at its best and most disastrous.
19
Bigflo & Oli: Hip Hop Frenzy (2020)
★ 7/10Also documentary
Go backstage with French rap duo Bigflo & Oli in this intimate music documentary, then join the superstar siblings as they embark on a major tour.
20
The Bus: A French Football Mutiny (2026)
★ 6.9/10Also documentary
This documentary revisits the French football team's controversial 2010 World Cup and the bus strike that sparked global headlines and national outrage.