While it was a bomb, Mystery Men still made over $35m and has become a cult film. Something else with Ben Stiller that fits better would be Zero Effect:
Daryl Zero is a private investigator and—along with his assistant, Steve Arlo—he solves impossible crimes and puzzles. Although Daryl's a master investigator, he doesn't know what to do with himself when he's not working; he has no social skills, writes bad music and drives Steve crazy.
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With him alongside Bill Pullman, Ryan O'Neal, Kim Dickens and Angela Featherstone. Made less than $2m, and isn't widely known (but is very good!). Or...
A New Yorker moves to Los Angeles in order to figure out his life while he housesits for his brother, and he soon sparks with his brother's assistant.
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Ben Stiller, Greta Gerwig, Brie Larson, Jennifer Jason Leigh, Rhys Ifans, Mark Duplass, Dave Franco, blah blah. $7.4m. And yet another Ben Stiller:
Adopted as a child, new father Mel Colpin decides he cannot name his son until he knows his birth parents, and determines to make a cross-country quest to find them. Accompanied by his wife, Nancy, and an inept yet gorgeous adoption agent, Tina, he departs on an epic road trip that quickly...
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Ben Stiller, Patricia Arquette, Teo Leoni, Alan Alda, Lily Tomlin, Richard Jenkins, Josh Brolin, Mary Tyler Moore and more. $14.7m. Maybe doesn't fit because it didn't actually bomb.
One of Richard Linklater's best films (and that has aged like fine wine post-MeToo), Tape:
Three old high school friends meet in a Michigan motel room to dissect painful memories from their past.
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Stars Ethan Hawke, Robert Sean Leonard and Uma Thurman (they're the only three characters in it). Made $500k.
A criminal subculture operates among U.S. soldiers stationed in West Germany just before the fall of the Berlin wall.
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Joaquin Phoenix, Ed Harris, Anna Paquin, Michael Pena, Scott Glenn, Dean Stockwell, Idris Elba, Elizabeth McGovern, blah blah. $2.3m
Nick is the director of a low-budget indie film. He tries to keep everything together as his production is plagued with an insecure actress, a megalomaniac star, a pretentious, beret-wearing director of photography, and lousy catering.
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Steve Buscemi, Katherine Keener, Dermot Mulroney, Peter Dinklage, plus a bunch of on sight but not name actors. $1.1m BO.
Various individuals think they’re coming together for a party in a private home, but a series of revelations results in a huge crisis that throws their belief systems – and their values – into total disarray.
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Has Cillian Murphy, Patricia Clarkson, Timothy Spall, Emily Mortimer, Kristin Scott Thomas, Bruno Ganz and Cherry Jones in it. $5.5m.
Two young women and their friends spend spare time at an exclusive nightclub in 1980s New York.
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Features Kate Beckinsale, Chloe Sevigny, Robert Sean Leonard, Jennifer Beals, Michael Weatherly, Chris Eigeman, etc (lots of folks recognisable by face but not by name), and made $3m. I kinda hesitated with this one because it's critically super well known and regarded, has a Criterion release, etc, but is still sub 30k watched on Letterboxd.
Margot Zeller is a short story writer with a sharp wit and an even sharper tongue. On the eve of her estranged sister Pauline's wedding to unemployed musician/artist/depressive Malcolm at the family seaside home, Margot shows up unexpectedly to rekindle the sisterly bond and offer her own brand...
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Nicole Kidman, Jack Black, Jennifer Jason Leigh, John Turturro and Ciaran Hinds. $3m.
A seven-year-old chess prodigy refuses to harden himself in order to become a champion like the famous but unlikable Bobby Fischer.
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Ben Kingsley, Laurence Fishburne, Joe Mantegna, Joan Allen, William H. Macy, Laura Linney, Tony Shalhoub, David Paymer, and so on. $7.2m
In 1980, Queens, New York, a young Jewish boy befriends a rebellious African-American classmate to the disapproval of his privileged family and begins to reckon with growing up in a world of inequality and prejudice.
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Anthony Hopkins, Anne Hathaway, Jeremy Strong, Jessica Chastain, plus child actors who will probably be big in the future. $6m.
And every Woody Allen film bar a few since the 80s, the casts of which would obliterate literally everything. For instance, Everyone Says I Love You:
A New York girl sets her father up with a beautiful woman in a shaky marriage while her half sister gets engaged.
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With Drew Barrymore, Edward Norton, Julia Roberts, Goldie Hawn, Natalie Portman, Natasha Lyonne, Alan Alda, Tim Roth, Billy Crudup, Lukas Haas and so on. $9.8m.
Everything mentioned here is a good movie btw (7/10 or above), made below $20m and has less than 50k people that have logged it on Letterboxd. Some are cheats because they're from well known directors, but I just went for the stuff that instantly came to mind instead of plumbing the depths.
One last thing is Heat Vision and Jack, which is a television pilot that wasn't picked up to series. It's from someone I haven't mentioned yet in this comment... Ben Stiller! But he directed it, and it's awesome. Stars Jack Black, Owen Wilson, Ron Silver, Christine Taylor and Vincent Schiavelli. It's also written by Dan Harmon and is about an astronaut who gained superintelligence by flying too close to the sun, and is now on the run from NASA with his talking motorbike.
You can watch it here:
Heat Vision and Jack was created as a 1999 pilot for Fox. Written by Dan Harmon and Rob Schrab, directed by Ben Stiller, this series was passed over by Fox d...
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View: https://www.youtube.com/watch?v=6lWgXDOAJ5s
Curses, you beat me to it while I was typing :P!
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