Movies Like The 100 Funniest Moments of the 20th Century: The Unexpected

If you liked The 100 Funniest Moments of the 20th Century: The Unexpected (1995), a comedy and documentary movie directed by John C. Feld and Wendy Maples, 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
Kevin Hart: Seriously Funny (2010)
★ 7/10Also comedy and documentary
Fresh off the heels of appearing in movies like Superhero Movie and The 40 Year-Old Virgin, fast-talking comedian Kevin Hart stars in his second live stand-up performance in Cleveland, Ohio, where he makes fun of…
2
Tropic Thunder: Rain of Madness (2008)
★ 6.8/10Also comedy and documentary
A behind-the-scenes mockumentary of Tropic Thunder.
3
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.
4
Jerry Before Seinfeld (2017)
★ 6.7/10Also comedy and documentary
Jerry Seinfeld returns to the club that gave him his start in the 1970s, mixing iconic jokes with stories from his childhood and early days in comedy.
5
Who Are You, Charlie Brown? (2021)
★ 6.9/10Also documentary
Lupita Nyong'o narrates a documentary about Peanuts and its creator, Charles M. Schulz. Famous fans—including Drew Barrymore, Kevin Smith, and Al Roker—share its influence on them, and a new animated story finds…
6
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).
7
Kevin Hart: Irresponsible (2019)
★ 6.7/10Also comedy and documentary
Stand-up comedian Kevin Hart talks about his family, travel and a year full of reckless behavior in front of a live sold-out crowd in London.
8
This Filthy World (2006)
★ 7.6/10Also documentary and comedy
In this filmed version of cult film director John Waters' popular one-man show, the Pink Flamingos and A Dirty Shame director takes the stage to discuss everything from his early influences, fondest career memories…
9
Western Stars (2019)
★ 7/10Also documentary
The incomparable Bruce Springsteen performs his critically acclaimed latest album and muses on life, rock, and the American dream, in this intimate and personal concert film co-directed by Thom Zimny and Springsteen…
10
David Byrne's American Utopia (2020)
★ 7.5/10Also documentary
A filmed version of David Byrne's Broadway show, a unifying musical celebration that inspires audiences to connect to each other and to the global community.
11
Billie Eilish - Hit Me Hard and Soft: The Tour (Live in 3D) (2026)
★ 8.4/10Also documentary
Captured during Billie Eilish's sold-out world tour, a concert experience from one of the most celebrated and successful artists of her generation, presented in immersive 3D.
12
An Evening with Kevin Smith 2: Evening Harder (2006)
★ 7.1/10Also comedy and documentary
In this second Q&A with Kevin Smith he now enters the homes of some of his fans in Toronto and London.
13
LCD Soundsystem: Shut Up and Play the Hits (2012)
★ 6.9/10Also documentary
An intimate portrait of Brooklyn-based electronic rock band LCD Soundsystem's then-final live show on April 2, 2011, capturing both the exuberant, three-hour farewell concert at New York City's Madison Square Garden…
14
High School Musical: The Musical: The Holiday Special (2020)
★ 7.4/10Also documentary
The cast of “High School Musical: The Musical: The Series” delivers an abundance of feel-good holiday cheer as they perform their favorite Christmas, Hanukkah and New Year’s songs and share their fondest holiday…
15
The Great Buster: A Celebration (2018)
★ 7.2/10Also documentary and comedy
A celebration of the life and career of one of America's most influential and celebrated filmmakers and comedians—Buster Keaton—whose singular style and fertile output during the silent era created his legacy as a true…
16
Beyond Infinity: Buzz and the Journey to Lightyear (2022)
★ 7/10Also documentary
Explore the evolution of Buzz Lightyear from toy to human in the making of Pixar’s Lightyear. Dive into the origin and cultural impact of everyone’s favorite Space Ranger, the art of designing a new “human Buzz,” and…
17
Looking for Richard (1996)
★ 6.8/10Also documentary
Al Pacino's deeply-felt rumination on Shakespeare's significance and relevance to the modern world through interviews and an in-depth analysis of "Richard III."
18
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.
19
OLIVIA RODRIGO: driving home 2 u (a SOUR film) (2022)
★ 7.8/10Also documentary
Grammy® winner singer-songwriter Olivia Rodrigo takes a familiar road trip from Salt Lake City, where she began writing her debut album “SOUR,” to Los Angeles. Along the way, Rodrigo recounts the memories of writing…
20
Live Aid (1985)
★ 7.8/10Also documentary
Live Aid was held on 13 July 1985, simultaneously in Wembley Stadium in London, England, and the John F. Kennedy Stadium in Philadelphia, United States. It was one of the largest scale satellite link-ups and television…