Movies Like On Tiptoe: Gentle Steps to Freedom

If you liked On Tiptoe: Gentle Steps to Freedom (2000), a documentary movie directed by Eric Simonson, 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
Come See Me in the Good Light (2025)
★ 7.1/10Also documentary
In an intimate and joyful story of love in the face of loss, celebrated poets Andrea Gibson and Megan Falley find strength—and unexpected hilarity—in what might be their final year together.
2
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…
3
Anna Nicole Smith: You Don't Know Me (2023)
★ 6.1/10Also documentary
From the heights of her modeling fame to her tragic death, this documentary reveals Anna Nicole Smith through the eyes of the people closest to her.
4
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
5
A Toxic Love Story (2026)
★ 6.4/10Also documentary
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
6
Elstree 1976 (2015)
★ 6.2/10Also documentary
A documentary about ten very different lives connected by having appeared onscreen wearing masks or helmets in Star Wars.
7
180° South (2010)
★ 7.3/10Also documentary
The film follows adventurer Jeff Johnson as he retraces the epic 1968 journey of his heroes Yvon Chouinard and Doug Tompkins to Patagonia.
8
Terms and Conditions May Apply (2013)
★ 7/10Also documentary
Have you ever read the Terms and Conditions and Privacy Policies connected to every website you visit, phone call you make, or app you use? Of course you haven’t. But those agreements allow corporations to do things…
9
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.
10
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.
11
The Class of ‘92 (2013)
★ 7.1/10Also documentary
A detailing of the rise to prominence and global sporting superstardom of six supremely talented young Manchester United football players (David Beckham, Nicky Butt, Ryan Giggs, Paul Scholes, Phil and Gary Neville)…
12
Ex Libris: The New York Public Library (2017)
★ 6.4/10Also documentary
A documentary about how a dominant cultural and demographic institution both sustains their traditional activities and adapts to the digital revolution.
13
Looking for Richard (1996)
★ 6.8/10Also documentary
Al Pacino's deeply-felt rumination on Shakespeare's significance and relevance to the modern world through interviews and an in-depth analysis of "Richard III."
14
Unknown Number: The High School Catfish (2025)
★ 6.7/10Also documentary
Vulgar, taunting texts blow up the phones of a teen and her boyfriend. Who's sending them — and why? This twisty documentary reveals the shocking answer.
15
Harmontown (2014)
★ 6.6/10Also documentary
A comedic, brutally honest documentary following self-destructive TV writer Dan Harmon as he takes his live podcast on a national tour.
16
Black Sheep (2018)
★ 7.2/10Also documentary
After the high-profile killing of Damilola Taylor, Cornelius' family move out of London. But when they discover their new town is run by racists, Cornelius takes a drastic step to survive.
17
Above Majestic (2018)
★ 7.4/10Also documentary
A look at the origins, history and conspiracies behind the "Majestic 12", a clandestine group of military and corporate figureheads charged with reverse-engineering extraterrestrial technology.
18
21 Up (1977)
★ 7.4/10Also documentary
After another 7 year wait, director Michael Apted revisits the same group of British-born children from Seven Up! and 7 Plus Seven. The subjects are interviewed as to the changes that have occurred in their lives…
19
Drew: The Man Behind the Poster (2013)
★ 7/10Also documentary
A documentary on legendary movie-poster artist Drew Struzan.
20
The Secret (2006)
★ 6.6/10Also documentary
Interviews with leading authors, philosophers and scientists, with an in-depth discussion of the Law of Attraction. The audience is shown how they can learn and use 'The Secret' in their everyday lives.