Movies Like Microsoft Windows 95 Video Guide

If you liked Microsoft Windows 95 Video Guide (1995), a documentary and comedy movie directed by Dominick Rossetti, 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
An Evening with Kevin Smith (2002)
★ 7.4/10Also comedy and documentary
Kevin Smith interacts in Q&A sessions throughout various college stops in the USA.
2
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.
3
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.
4
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.
5
American Pie: Revealed (2004)
★ 6/10Also documentary and comedy
Documentary about the making of American Pie (1999), American Pie 2 (2001) and American Wedding (2003).
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
Aziz Ansari: Right Now (2019)
★ 7.1/10Also comedy and documentary
In a comedy special directed by Spike Jonze, Aziz Ansari shares deep personal insights and hilarious takes on wokeness, family and the social climate.
8
Robin Williams: Live on Broadway (2002)
★ 7.8/10Also comedy and documentary
2002 HBO Stand-up Special starring Robin Williams. Recorded and broadcast live from New York City's Broadway Theater at the culmination of his historic 2002 sold-out tour, this special finds the Oscar-winning…
9
Chris Brown: Welcome to My Life (2017)
★ 6.4/10Also documentary
This compelling Documentary moves beyond the spotlight and past the attention-grabbing headlines to give pop superstar Chris Brown a chance to tell his own story. New interviews with the international phenomenon reveal…
10
Carrie Fisher: Wishful Drinking (2010)
★ 7.3/10Also documentary and comedy
"Wishful Drinking" is based on Fisher's memoirs of the same title. The stage adaptation had its world premiere in 2006 at the Geffen Playhouse in L.A. It later played at Berkeley Repertory before opening on Broadway in…
11
American Movie (1999)
★ 7.5/10Also documentary and comedy
American Movie documents the story of filmmaker Mark Borchardt, his mission, and his dream. Spanning over two years of intense struggle with his film, his family, financial decline, and spiritual crisis, American Movie…
12
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…
13
The Curse of the Dragon (1993)
★ 7.2/10Also documentary
A 1993 documentary film about Bruce Lee. The film includes interviews from some of his fellow students and opponents who worked alongside him in his movies.
14
Lucy and Desi (2022)
★ 7.1/10Also documentary
Explore the unlikely partnership and enduring legacy of one of the most prolific power couples in entertainment history. Lucille Ball and Desi Arnaz risked everything to be together.
15
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.
16
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…
17
The Amazing Johnathan Documentary (2019)
★ 6.1/10Also documentary and comedy
What begins as a documentary following the final tour of a dying magician - "The Amazing Johnathan" - becomes an unexpected and increasingly bizarre journey as the filmmaker struggles to separate truth from illusion.
18
Jackass Presents: Bad Grandpa .5 (2014)
★ 6/10Also comedy and documentary
Bad Grandpa .5 gives you a whole new perspective on the world of Irving Zisman with bonus scenes and pranks also featuring Spike Jonze as "Gloria" and Catherine Keener as Irving's wife "Ellie", plus a look at the…
19
42 Up (1999)
★ 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.
20
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.