Movies Like Rat Pack: A Conference of Cool

If you liked Rat Pack: A Conference of Cool (1999), a documentary and history movie, 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
Making Waves: The Art of Cinematic Sound (2019)
★ 6.9/10Also documentary and history
The history of cinematic sound, told by legendary sound designers and visionary filmmakers.
2
9/11: Inside the President's War Room (2021)
★ 6.9/10Also documentary and history
Experience the events of September 11, 2001 through the eyes of President Bush and his closest advisors as they personally detail the crucial hours and key decisions from that historic day.
3
Cover-Up (2025)
★ 7.2/10Also documentary and history
He's devoted his career to uncovering stories the powerful want buried. From My Lai to Abu Ghraib, dig into the life's work of journalist Seymour Hersh.
4
The Soviet Story (2008)
★ 7.3/10Also documentary and history
“The Soviet Story” is a story of an Allied power, which helped the Nazis to fight Jews and which slaughtered its own people on an industrial scale. Assisted by the West, this power triumphed on May 9th, 1945. Its…
5
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…
6
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.
7
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…
8
The Unknown Known (2013)
★ 6.8/10Also documentary and history
Former United States Secretary of Defense Donald Rumsfeld discusses his career in Washington D.C. from his days as a congressman in the early 1960s to planning the invasion of Iraq in 2003.
9
The Mystery of D.B. Cooper (2020)
★ 6.3/10Also documentary and history
This documentary brings to life the stories of four people believed by their family and friends to be “DB Cooper,” a man who hijacked a 727 flying out of Seattle and jumped from the plane over the wilds of Washington…
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
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.
12
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.
13
Los Angeles Plays Itself (2004)
★ 7.6/10Also documentary and history
From its distinctive neighborhoods to its architectural homes, Los Angeles has been the backdrop to countless movies. In this dazzling work, Andersen takes viewers on a whirlwind tour through the metropolis' real and…
14
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
15
Bad 25 (2012)
★ 7.3/10Also documentary
Spike Lee pays tribute to Michael Jackson's Bad on the twenty-fifth anniversary of the epochal album, offering behind-the-scenes footage of Jackson recording the album and interviews with confidants, musicians…
16
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.
17
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…
18
Room 237 (2012)
★ 6.1/10Also documentary
A subjective documentary that explores various theories about hidden meanings in Stanley Kubrick's classic film The Shining. Five very different points of view are illuminated through voice over, film clips, animation…
19
Inside Deep Throat (2005)
★ 6.4/10Also documentary and history
In 1972, a seemingly typical shoestring budget pornographic film was made in a Florida hotel: "Deep Throat," starring Linda Lovelace. This film would surpass the wildest expectation of everyone involved to become one…
20
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.