8 Best Movies to Watch by Bill Hader

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1. Barry, 2022

Former SNL cast member and comedy legend Bill Hader is the writer and main protagonist of the HBO-produced and three-time Emmy-winning series Barry. Part psychological thriller, part dark comedy – one of many new series in the “dramedy” genre – deals with the unlikely premise of a PTSD-ridden low-rent assassin, who, after travelling to LA to execute an actor, decides to dedicate his life to the amateur theatre scene. (Watch out for the always amazing Henry Winkler as the acting class teacher! He was rightly nominated for an Emmy for this performance.)

In typical Bill Hader fashion, this genre-mix is still a lot more comedy than thriller and one cannot help but root for hapless Barry, while he dodges one bullet after the other, as it were, navigating Chechnyan mobsters, the FBI, and his intense acting peers. A lovely, funny, and smart show about a seemingly emotionless guy trying to escape his past.

Genre: Action & Adventure, Comedy, Crime, Drama

Actor: Anthony Carrigan, Bill Hader, Henry Winkler, Sarah Burns, Sarah Goldberg, Stephen Root

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2. The Skeleton Twins, 2014

	

Directed and co-written by Craig Johnson (who made The Adolescents with Mark Duplass), The Skeleton Twins is a beautiful piece of drama, dealing with some dark themes. It does so with surprising success, given that the two main actors are seasoned comedians with little to no experience in the genre. And yet, it is precisely the two leads that turn this bleak comedy-drama into a somber, haunting, but beautiful watch. Bill Hader is amazing as the depressed and suicidal gay man, Milo, who is reunited with his estranged twin Maggie (Kristen Wiig) after a series of unfortunate events. Their attempts at repairing their fractured relationship also forces them to confront the trajectory of their own lives, while they rediscover their erstwhile childhood friendship and long-lost camaraderie. Again, don't expect a traditional comedy, but an honest display of the complexities of sibling relationships, mental health, and how conflict, compassion, and understanding fit into it all.
Genre: Drama
Actor: Adriane Lenox, Bill Hader, Boyd Holbrook, Cliff Moylan, David Garelik, Eddie Schweighardt, Genevieve Adams, Ian Hyland, Jennifer Lafleur, Joanna Gleason, Kathleen Rose Perkins, Kristen Wiig, Luke Wilson, Paul Castro Jr., Sydney Lucas, Truck Hudson, Ty Burrell
Director: Craig Johnson
Rating: R

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3. Documentary Now!, 2022

Fans of sketch comedy, documentaries, and the always-hilarious duo of Bill Hader and Fred Armisen are in for a treat with Documentary Now!, a delightful miniseries that both satirizes and pays tribute to the non-fiction format. Each episode parodies a particular documentary and tone, bringing the comedians and their ever-revolving roster of guest stars to different eras, regions, costumes, accents, and more.

With SNL veterans Hader and Armisen at the helm, this mockumentary is sure to amuse and impress even the most stoic among us, if not for the show's humor, then for its sharp attention to detail and endlessly creative references.

Genre: Comedy

Actor: Bill Hader, Fred Armisen, Helen Mirren, Irving Azoff

Rating: TV-14

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4. Adventureland, 2009

Adventureland is a retro-tinged movie about teens in Pittsburgh working at a run down amusement park during the summer of 1987. It is marketed as similar to Superbad, when in fact the only thing they have in common is the Director. Adventureland is funny, but it is more sweet, tender, and intimate. Touching on themes of unrequited love, returning home, and small-town love, the film stars Jesse Eisenberg, Kristen Stewart, and the always-delightful-duo of Bill Hader and Kristen Wiig. In addition, the film’s soundtrack is a joyous blast from the past, running the gamut of all your favorite 1980’s synth-happy love songs. It is a movie that anyone can really relate to, no matter when they were born, and an amazing watch.

Genre: Comedy, Drama, Romance

Actor: Adam Kroloff, Amy Landis, Ashtin Petrella, Barret Hackney, Bill Hader, Dan Bittner, Declan Baldwin, Eric Schaeffer, Erin Cappiccie, Ian Harding, Jack Gilpin, Jackson Nunn, Jesse Eisenberg, Josh Pais, Kelsey Ford, Kevin Breznahan, Kimisha Renee Davis, Kristen Stewart, Kristen Wiig, Lisa Lamendola, Marc Grapey, Margarita Levieva, Martin Starr, Mary Birdsong, Matt Bush, Michael Zegen, Paige Howard, Russell Steinberg, Ryan McFarland, Ryan Reynolds, Stephen Mast, Todd Cioppa, Vanessa Hope, Wendie Malick

Director: Greg Mottola

Rating: R

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5. The Great Buster: A Celebration, 2018

In his last film, American Serb film historian Peter Bogdanovich celebrates silver screen legend Buster Keaton. The subject alone is compelling to watch. It would be easy to pull clips from Keaton’s works, dig through the headlines, pull in some celebrity interviews, and call it a day. However, in Bogdanovich’s hands, this documentary handles Keaton with respect. Instead of focusing on the scandals, Bogdanovich focuses on Keaton’s brilliant work. Instead of reciting facts, Bogdanovich highlights how his bits influenced film today. Excellent editing - cuts, structure, and scoring - helps us glide through Keaton’s work. The film truly understands Keaton’s life and exactly why he’s brilliant. Comprehensive yet very focused, this documentary honestly feels better than film school.

Genre: Comedy, Documentary, Drama

Actor: Ben Mankiewicz, Bill Hader, Bill Irwin, Buster Keaton, Carl Reiner, Cybill Shepherd, Dick Van Dyke, Eleanor Keaton, French Stewart, James Karen, Johnny Knoxville, Jon Watts, Leonard Maltin, Mel Brooks, Nick Kroll, Norman Lloyd, Orson Welles, Paul Dooley, Peter Bogdanovich, Quentin Tarantino, Richard Lewis, Tom Holland, Werner Herzog

Director: Peter Bogdanovich

Rating: Not Rated

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6. Beastie Boys Story, 2020

Beastie Boys Story, a live documentary that runs for two hours and consists entirely of two speakers presenting a PowerPoint onstage, shouldn't be as enjoyable and enthralling as it is, but with the help of director Spike Jonze, remaining band members Mike D and Adam Horovitz pull off the impossible and draw in a rapt crowd by chronicling how the iconic hip-hop group came to be.

Told with intimate detail and blithe humor, Beastie Boys Story has the easygoing charm of a dear friend recounting the good old days with you. Mike D and Adam Horovitz are skilled storytellers, and with Jonze operating the technicals to a tee backstage, everything comes together in a satisfyingly smooth and utterly watchable take. You don't have to know much (if anything at all) about the Beastie Boys to enjoy this documentary, and whatever your opinion is of them beforehand, you'll leave this film knowing a bit more about the creative process, necessary growth, and unbelievable luck all artists go through.

Genre: Documentary, Music

Actor: Adam Curry, Adam Horovitz, Adam Yauch, Afrika Bambaataa, Ben Stiller, Bill Hader, David Cross, Dick Clark, Don Cornelius, Joan Rivers, Karen Duffy, Kurt Loder, Kurtis Blow, Madonna, Michael Diamond, Michael Kenneth Williams, Michael Stipe, Money Mark, Rick Rubin, Russell Simmons, Spike Jonze, Steve Buscemi, Tenzin Gyatso

Director: Spike Jonze

Rating: TV-MA

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7. Too Funny to Fail: The Life & Death of The Dana Carvey Show, 2017

	
Too Funny to Fail isn’t just a documentary about funny people. It’s a documentary that’s hilarious in its own right. Director Josh Greenbaum assembles the comedic powerhouse behind the short-lived Dana Carvey Show and has them recall the idiosyncratic, subversive skits they did on the show. They are, of course, naturally funny, but it’s the questions Greenbaum asks them off-cam, the clips he shows, and the titles he picks for them (Bill Hader, as a fan who used to watch the show in lieu of going to classes, is stuck with “once skipped school”) that gives the documentary its own comedic signature. The spectacular failure of The Dana Carvey Show is also an inspirational story of sorts, given the astronomical success its staff and cast have and are continuing to enjoy since its cancellation.Genre: Comedy, Documentary
Actor: Bill Hader, Dana Carvey, Jon Glaser, Louis C.K., Robert Carlock, Robert Smigel, Spike Feresten, Stephen Colbert, Steve Carell
Director: Josh Greenbaum
Rating: NR

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8. Love, Gilda, 2018

	
It’s hard not to botch a documentary about one of the most endearing, beloved, and talented celebrities to come out of the industry, so in subject matter alone, Love, Gilda is a winner. But director Lisa Dapolito rightly understands that Radner’s life is more than just the usual Hollywood story of stumbling into fame and fortune as she mines something quite special out of Radner’s journey. More than a biography, Love, Gilda is also a manifesto for female comedians, a relatable tale of girlhood, and a comforting message for those afflicted with similar illnesses that they’re not alone. Also, by the end, it turns into a great love story you can’t help but long for.Genre: Documentary
Actor: Alan Zweibel, Amy Poehler, Bill Hader, Bill Murray, Cecily Strong, Chevy Chase, Gene Wilder, Gilda Radner, Laraine Newman, Lorne Michaels, Martin Short, Maya Rudolph, Melissa McCarthy, Paul Shaffer
Director: Lisa D’Apolito

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