392 Best Quirky Movies to Watch (Page 15)

Told in a playful mockumentary format, Pinball: The Man Who Saved the Game delivers precisely what the title promises and a bit more. Apart from imparting interesting information about pinball's complicated past (it was only declared legal in New York as recently as 1976), the film doubles as a touching family drama and a fun experiment on genre. As Robert Sharpe, the real-life games expert who helped decriminalize pinball, Mike Faist is winsome, compelling, and maybe the best thing about the film.

While Pinball could've leaned into its silliness more instead of just dipping its toes in avant-garde territory, the film is pleasant enough with plenty of fun and tender moments to enjoy. 

Genre: Comedy, Drama, History, Romance

Actor: Bryan Batt, Christopher Convery, Connor Ratliff, Crystal Reed, Damian Young, Dennis Boutsikaris, Donna Del Bueno, Eric William Morris, Hope Blackstock, Jake Regal, Kenneth Tigar, Michael Kostroff, Mike Doyle, Mike Faist, Rosa Arredondo, Supriya Ganesh, Toby Regbo, Zac Jaffee

Director: Austin Bragg, Meredith Bragg

Going to sleep is something we do every day, though, when we were kids, it certainly wasn’t easy. With family-friendly source material and a new (and adorable!) sleepytime ensemble, Orion and the Dark plays with this fact of childhood, but screenwriter Charlie Kaufman transforms it into something more as the title characters journey into literal midnight dreams, tell stories-within-stories, and return back home with a poetic repetition. It still has some of his existential despair– after all, the overly imaginative Orion literally contemplates the possibility of death through his many, many anxieties– but it doesn’t just play with the classic childhood fear. Kaufman transforms the bedtime story, and the act of storytelling itself, as co-creation and connection between generations of filmmakers and viewers, with this film’s surprisingly layered writing.

Genre: Animation, Comedy, Family, Fantasy

Actor: Aliki Theofilopoulos, Amy Hill, Angela Bassett, Aparna Nancherla, Carla Gugino, Colin Hanks, Golda Rosheuvel, Hira Ambrosino, Ike Barinholtz, Jack Fisher, Jacob Tremblay, Matt Dellapina, Nat Faxon, Natasia Demetriou, Nick Kishiyama, Paul Walter Hauser, Ren Hanami, Sean Charmatz, Shannon Chan-Kent, Sky Alexis, Toru Uchikado, Walt Dohrn, Werner Herzog

Director: Sean Charmatz

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Barbara George-Reiss, Cassie Townsend, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Heath Young, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Josh Bond, Justin Possenti, K. Todd Lytle, Kinna McInroe, Kyle Scott Jackson, Linda Wakeman, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, R.C. Keene, Richard Riehle, Ron Livingston, Rupert Reyes, Samantha Inoue Harte, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

With the powerful duo of queer aesthetics and rock n roll, Hedwig and the Angry Inch questions the duality between genders, lovers, and everything in between. Like the 1998 stage musical, the film follows the titular Hedwig and her band as they navigate the music scene for fame and love. The adaptation gives justice to their performances, giving the vibe of 70s glam rock music videos. The film is not without its flaws. Hedwig’s relationship with the younger Tommy Gnosis remains controversial. However, while Hedwig may not be a perfect representation of the trans experience– after all, she only chooses gender reassignment purely to leave East Germany– this cult film still remains a landmark for queer representation.

Genre: Comedy, Drama, Music

Actor: Alan Mandell, Alberta Watson, Andrea Martin, Ben Mayer-Goodman, Ermes Blarasin, Gene Pyrz, John Cameron Mitchell, Karen Hines, Maggie Moore, Mary Krohnert, Maurice Dean Wint, Michael Aronov, Michael Pitt, Michael Stevens, Miriam Shor, Rob Campbell, Rosie O'Donnell, Sook-Yin Lee, Stephen Trask, Taylor Abrahamse, Thérèse DePrez

Director: John Cameron Mitchell