Movies Like My Winnipeg: Live in Toronto

If you liked My Winnipeg: Live in Toronto (2008), a documentary movie directed by Guy Maddin, 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
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.
2
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.
3
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)…
4
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…
5
Justin Bieber's Believe (2013)
★ 6.9/10Also documentary
A backstage and on-stage look at Justin Bieber during his rise to super stardom.
6
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…
7
Billie Eilish - Hit Me Hard and Soft: The Tour (Live in 3D) (2026)
★ 8.4/10Also documentary
Captured during Billie Eilish's sold-out world tour, a concert experience from one of the most celebrated and successful artists of her generation, presented in immersive 3D.
8
No Half Measures: Creating the Final Season of Breaking Bad (2013)
★ 8.5/10Also documentary
A documentary about the making of season five of the acclaimed AMC series Breaking Bad.
9
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.
10
Dangerous Days: Making Blade Runner (2007)
★ 7.8/10Also documentary
The definitive 3½-hour documentary about the troubled creation and enduring legacy of the science fiction classic 'Blade Runner', culled from 80 interviews and hours of never-before-seen outtakes and lost footage.
11
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.
12
Seduced and Abandoned (2013)
★ 6.2/10Also documentary
SEDUCED AND ABANDONED combines acting legend Alec Baldwin with director James Toback as they lead us on a troublesome and often hilarious journey of raising financing for their next feature film. Moving from director…
13
American Boy: A Profile of Steven Prince (1978)
★ 6.7/10Also documentary
Martin Scorsese spends an evening with larger-than-life raconteur Steven Prince—a former drug addict, road manager for Neil Diamond, and actor—as he recounts stories from his colorful life.
14
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…
15
28 Up (1985)
★ 7.5/10Also documentary
Just two years away from turning 30, participants in Michael Apted's documentary series are facing serious questions of identity and purpose, wondering whether they've found their place in the world.
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
Lionel Messi: Destiny (2023)
★ 7.8/10Also documentary
Behind-the-scenes documentary about how Lionel Messi succeeded in lifting the World Cup – the only trophy to have eluded him in an incredible career.
18
Gilbert (2017)
★ 6.7/10Also documentary
The life and career of one of comedy's most inimitable modern voices, Mr. Gilbert Gottfried.
19
Capital in the Twenty-First Century (2019)
★ 6.5/10Also documentary
Film adaptation of French economist Thomas Piketty's ground-breaking global bestseller of the same name: an eye-opening journey through wealth and power.
20
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.