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Best Documentary Movies With Your Boyfriend From The 2000S That Will Make You Laugh

The best documentary movies with your boyfriend from the 2000s that will make you laugh. Includes Won't You Be My Neighbor?, Free Solo, 13th and more — curat...

Watching a film together is one of the simplest and best things you can do. Pick something with enough texture that you'll want to pause it and argue about it.

Looking back, the 2000s were a golden era for this kind of filmmaking — studios still willing to fund serious work, directors still pushing at the edges of what was expected.

A great documentary finds the universal in the specific. One person's story becomes everyone's story.

Won't You Be My Neighbor? movie poster
1
2018 · ★★★★☆ 8.4/10

An intimate look at America's favourite neighbor and the life, lessons, and legacy of Fred Rogers.

Free Solo movie poster
2
2018 · ★★★★☆ 8.2/10

Follow Alex Honnold as he attempts to become the first person to ever free solo climb Yosemite's El Capitan.

13th movie poster
3
2016 · ★★★★☆ 8.2/10

An in-depth look at the US prison system and how it reveals the nation's history of racial inequality.

Searching for Sugar Man movie poster
4
2012 · ★★★★☆ 8.2/10

Two South Africans set out to discover what happened to their musical hero, the mysterious 1970s rock musician Rodriguez.

Amy movie poster
5
2015 · ★★★½☆ 7.8/10

The story of Amy Winehouse, in her own words, featuring archival footage and recordings.

What makes a documentary essential viewing is specificity. These films don't deal in generalities — they follow real people making impossible choices in real moments.

Man on Wire movie poster
6
2008 · ★★★½☆ 7.7/10

A look at tightrope walker Philippe Petit's daring, and illegal, high-wire routine performed between the World Trade Center's twin towers in 1974.

Icarus movie poster
7
2017 · ★★★½☆ 7.9/10

When Bryan Fogel sets out to uncover the truth about doping in sports, a chance meeting with a Russian scientist transforms his project into a geopolitical thriller.

The Act of Killing movie poster
8
2012 · ★★★★☆ 8.2/10

A documentary about the 1965-66 Indonesian mass killings, in which former paramilitary leaders re-enact their crimes.

20 Feet from Stardom movie poster
9
2013 · ★★★½☆ 7.8/10

Backup singers discuss their careers and relationships with the stars they support.

Bowling for Columbine movie poster
10
2002 · ★★★★☆ 8.0/10

Michael Moore explores the culture of guns and violence in the United States.

The best comedies don't try to be funny. They build worlds with such specificity that the humour arrives naturally. These films know that.

A great documentary is one you find yourself thinking about weeks later. These qualify.