Movies Like F. Scott Fitzgerald: Winter Dreams

If you liked F. Scott Fitzgerald: Winter Dreams (2001), a documentary movie directed by DeWitt Sage, 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
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)…
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
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.
5
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…
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
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.
8
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.
9
Charlie: The Life and Art of Charles Chaplin (2003)
★ 7/10Also documentary
Brilliant, long in-the-works story of the life and art of the world's greatest comedian and the cinema's first genius, Charlie Chaplin. Produced, written and directed by renowned film critic Richard Schickel.
10
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.
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
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
13
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.
14
Travis Scott: Look Mom I Can Fly (2019)
★ 6.8/10Also documentary
While crafting his Grammy-nominated album "Astroworld," Travis Scott juggles controversy, fatherhood and career highs in this intimate documentary.
15
Shawn Mendes: In Wonder (2020)
★ 8.1/10Also documentary
A portrait of singer-songwriter Shawn Mendes' life, chronicling the past few years of his rise and journey.
16
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.
17
Drew: The Man Behind the Poster (2013)
★ 7/10Also documentary
A documentary on legendary movie-poster artist Drew Struzan.
18
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.
19
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.
20
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.