Movies Like Frank Sinatra: The Vintage Years

If you liked Frank Sinatra: The Vintage Years (1997), a documentary movie directed by Ted Newsom, 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
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.
2
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.
3
McQueen (2018)
★ 7.4/10Also documentary
Alexander McQueen's rags-to-riches story is a modern-day fairy tale, laced with the gothic. Mirroring the savage beauty, boldness and vivacity of his design, this documentary is an intimate revelation of McQueen's own…
4
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…
5
Deliver Us from Evil (2006)
★ 7.2/10Also documentary
Documentary filmmaker Amy Berg investigates the life of 30-year pedophile Father Oliver O'Grady and exposes the corruption inside the Catholic Church that allowed him to abuse countless children. Victims' stories and a…
6
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.
7
Fuck (2006)
★ 6.4/10Also documentary
A documentary on the expletive's origin, why it offends some people so deeply, and what can be gained from its use.
8
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.
9
Cameraperson (2016)
★ 6.7/10Also documentary
As a visually radical memoir, CAMERAPERSON draws on the remarkable footage that filmmaker Kirsten Johnson has shot and reframes it in ways that illuminate moments and situations that have personally affected her. What…
10
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…
11
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.
12
Bright Lights: Starring Carrie Fisher and Debbie Reynolds (2016)
★ 7.4/10Also documentary
An intimate portrait of Hollywood royalty featuring Debbie Reynolds, Todd Fisher, and Carrie Fisher.
13
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.
14
Spielberg (2017)
★ 7.5/10Also documentary
A documentary on the life and career of one of the most influential film directors of all time, Steven Spielberg.
15
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…
16
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.
17
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.
18
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
19
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.
20
S4: The Bob Lazar Story (2026)
★ 8.4/10Also documentary
Over 35 years after Bob Lazar's revelations, this documentary exposes secrets of a facility the government still denies. Featuring Lazar's testimony, recreations, and new evidence, it reopens a case that continues to…