Movies Like 'Oh, Miss Jones!': The Very Best of Leonard Rossiter

If you liked 'Oh, Miss Jones!': The Very Best of Leonard Rossiter (1996), a documentary movie directed by Duncan Smith and Will Trotter, 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
Gilbert (2017)
★ 6.7/10Also documentary
The life and career of one of comedy's most inimitable modern voices, Mr. Gilbert Gottfried.
2
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.
3
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.
4
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
5
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.
6
Drew: The Man Behind the Poster (2013)
★ 7/10Also documentary
A documentary on legendary movie-poster artist Drew Struzan.
7
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.
8
As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)
★ 7.8/10Also documentary
A compilation of over 30 years of private home movie footage shot by Lithuanian-American avant-garde director Jonas Mekas, assembled by Mekas "purely by chance", without concern for chronological order.
9
For the Love of Spock (2016)
★ 7.4/10Also documentary
The life of Mr. Spock, as well as that of Leonard Nimoy, the actor who played him for almost fifty years, written and directed by his son: Adam.
10
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.
11
Love, Marilyn (2013)
★ 6.5/10Also documentary
Using the book 'Fragments', which collects Marilyn Monroe's poems, notes and letters, and with participation from the Arthur Miller and Truman Capote estates who have contributed more material, each of the actresses…
12
Halloween: 25 Years of Terror (2006)
★ 6.8/10Also documentary
Follow the evolution of the 'Halloween' movies over the past twenty-five years. It examines why the films are so popular and revisits many of the original locations used in the films - seeing the effects on the local…
13
David Bowie: Five Years (2013)
★ 7.5/10Also documentary
Featuring a wealth of previously unseen archive, this film looks at how Bowie continually evolved: from Ziggy Stardust to the Soul Star of Young Americans, to the ‘Thin White Duke’. It explores his regeneration in…
14
The Crystal Calls - Making The Dark Crystal: Age of Resistance (2019)
★ 7.5/10Also documentary
Go behind the scenes with stars, puppeteers and creators as they bring Jim Henson's magical world of Thra back to life in a sweeping fantasy series.
15
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…
16
Harry Dean Stanton: Partly Fiction (2013)
★ 6.9/10Also documentary
An impressionistic portrait of the iconic actor Harry Dean Stanton comprised of intimate moments, film clips from some of his 250 films and his renditions of American folk songs.
17
I Am Heath Ledger (2017)
★ 7.4/10Also documentary
The life and career of an actor, artist, and icon. His own journey through his own camera.
18
The Summers of It - Chapter Two: It Ends (2019)
★ 7.1/10Also documentary
This documentary focuses on the actors and their journey over two summers to create the remake to the original IT, by Stephen King. The documentary originally released as bonus material, bundled with IT: Chapter Two.
19
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."
20
35 Up (1991)
★ 7.6/10Also documentary
Director Michael Apted revisits the same group of British-born adults after a 7 year wait. The subjects are interviewed as to the changes that have occurred in their lives during the last seven years.