Most Similar Movies to Vince Vaughn's Wild West Comedy Show: 30 Days & 30 Nights - Hollywood to the Heartland (2006)
If you are looking for movies like Vince Vaughn's Wild West Comedy Show: 30 Days & 30 Nights - Hollywood to the Heartland (2006), you might like movies tagged with keyword : comedy, documentary, humor, actors, behind the scenes, live performance, road movie, audience interaction, hollywood, music, cultural differences, american culture, entertainment, performing arts, filmmaking, independent film, true story, fans, journey, vince vaughn .
95 Miles to Go (2004), Blue Collar Comedy Tour: The Movie (2003), The Original Kings of Comedy (2000), Heckler (2007), Kevin Hart: What Now? (2016), Dave Chappelle's Block Party (2005), Comedian (2002) ... Let's take a look at the following list...

95 Miles to Go (2004)
The hilarious intimacy of two comedians locked in a car together for hundreds of miles. Together, they each struggle with Ray's obsessions, phobias and insecurities in this unscripted exploration of newfound fame.
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Blue Collar Comedy Tour: The Movie (2003)
The comedic stylings of four sort-of famous funnymen are brought to the big screen courtesy of this 2002 documentary.
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The Original Kings of Comedy (2000)
A concert film featuring four major African American stand up comedians.
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Heckler (2007)
Comedian Jamie Kennedy shows just how nasty and mean the fight is between those in the spotlight and those in the dark
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Kevin Hart: What Now? (2016)
Comic Kevin Hart performs his stand-up routine in front of 50,000 people at Lincoln Financial Field in Philadelphia.
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Dave Chappelle's Block Party (2005)
A mix of Dave Chappelle's sketch comedy and musical interludes, inspired in part by the 1973 documentary Wattstax.
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Comedian (2002)
A look at the work of two stand-up comics, Jerry Seinfeld and a lesser-known newcomer, detailing the effort and frustration behind putting together a successful act and career while living a life on the road.
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Dying Laughing (2016)
The craft, creative process and complicated lives of stand-up comedians.
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Martin Lawrence Live: Runteldat (2002)
After undergoing a number of personal crises, a stand-up comic returns to the stage for a one-man show featuring stinging social commentary and very personal reflections about his life.
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Trust Us, This Is All Made Up (2009)
Given the flawless results, it's hard to believe that comedians David Pasquesi and T.J. Jagodowski make up their entire act on the spot. This documentary records one of the long-running improv duo's hilarious performances at New York City's Barrow Street Theatre. The film also goes behind the scenes as the pair strategizes for that night's act, discusses the nuances of their creative partnership and reflects on their training at Chicago's The Second City improv troupe.
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Festival (2005)
Following a number of performers and judges who converge at the annual Edinburgh Fringe Festival. Several tales are interwoven as the judge of a comedy award drives his personal assistant to distraction (and the bottle), a would-be comedienne tries to get her big break, and an actress mounts her earnest and challenging one-woman play.
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See What I'm Saying: The Deaf Entertainers Documentary (2010)
This inspirational documentary follows four deaf entertainers: a comic, drummer, actor and a singer as they attempt to cross over to mainstream audiences. These uniquely talented entertainers overcome great challenges to celebrate success.
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Buster Keaton Rides Again (1965)
This film is a documentary about the filming of one of Buster Keaton's movies: The Railrodder (1965).
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The Grand Role (2004)
Through archival footage and dramatic readings of his personal writings, the life of Nazi Germany's Propaganda Minister, Josef Goebbels, is examined.
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Best Worst Movie (2009)
A look at the making of the film Troll 2 (1990) and its journey from being crowned the "worst film of all time" to a cherished cult classic.
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Air Guitar Nation (2006)
The guitars may be fake, but the talent is real at the U.S. Air Guitar Championships, where performers rock out on invisible guitars in hilarious ways.
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The Amazing Johnathan Documentary (2019)
What begins as a documentary following the final tour of a dying magician - "The Amazing Johnathan" - becomes an unexpected and increasingly bizarre journey as the filmmaker struggles to separate truth from illusion.
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American: The Bill Hicks Story (2010)
Interviews and clever use of still photographs illustrate the life of a talented but often controversial comic who died of cancer at age 32.
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