9 Best Movies to Watch by Molly Shannon

Staff & contributors

Dorky kid Greg Gaines (played by the brilliant and unlikely named Thomas Mann) has severe issues with closeness (he calls his best friend a “co-worker”) and is instructed by his mother to befriend Rachel (Olivia Cooke), a girl recently diagnosed with cancer. Far from being an indie tear-jerker, though, “this isn't a touching romantic story”, as Greg's narration reminds us. This is not least to the quirky nature of the film and the third titular character Earl, Greg's closest co-worker, who acts as the moral glue between Greg and Rachel.

In addition to hilarious writing and amazing performances, the film is laced with pop-cultural references by way of the movies that Greg and his Earl shoot in their spare time – spoofy takes on cult movies with titles like Sockwork Orange. Moving without being melodramatic, Me and Earl and the Dying Girl is a charmingly off-kilter fish-out-of-water plot about making friends, dealing with death, and enjoying life best as one can.

Genre: Comedy, Drama

Actor: Alfonso Gomez-Rejon, Bobb'e J. Thompson, Chelsea Zhang, Connie Britton, Etta Cox, Hugh Jackman, Jackson Nunn, Jeremy Long, Joe Fishel, Jon Bernthal, Katherine Hughes, Masam Holden, Matt Bennett, Molly Shannon, Nick Offerman, Olivia Cooke, RJ Cyler, Thomas Mann

Director: Alfonso Gomez-Rejon

Rating: PG-13

Paul Giamatti, man. Ever watched Win/Win? What a performance. I didn’t think he could do any better than that. But here he did. This movie is now on Netflix. It’s about a couple that is trying to have a kid but can’t. Their frustration grows, but so does their willingness to do whatever it takes to become parents. They try to adopt, go to fertility clinics and ultimately ask their niece to donate her eggs. To really work, such a plot requires well-written, multifaceted characters one can relate to. I did, and it really worked.

Genre: Comedy, Drama

Actor: Alyssa Cheatham, Amaya Press, Caroline Martin, Danny Deferrari, Denis O'Hare, Desmin Borges, Emily Robinson, Fenton Lawless, Francesca Root-Dodson, Gabrielle Reidy, Hettienne Park, John Carroll Lynch, Kathryn Hahn, Katrine Hoyt, Kayli Carter, Kelly Miller, Kerry Flanagan, Lizzy DeClement, Maddie Corman, Molly Shannon, Paul Giamatti, Samantha Buck, Siobhan Fallon Hogan, Tracee Chimo

Director: Tamara Jenkins

Rating: R

Will and Harper’s premise is simple: two friends journey from one end of the States to another and, amid pit stops and bar hops, sunsets and beers, they talk about life, from its biggest concepts down to its tiniest details. The only difference in this case is that Will and Harper are navigating their friendship as well as the roads; since Harper has only recently transitioned (formerly, she was the comedy screenwriter Andrew Steele), she and Will feel the need to settle more than a few questions. When did this all start? What kept Harper from coming out? Will the friendship still be the same? Does Harper still like bad beer? Will, for his part, is earnest and curious, and though he fumbles along the way—at one point, he inadvertently exposes Harper to a transphobic crowd—he’s quick to recognize his mistakes, learn from them, and recenter our attention to Harper, who is the real star of this film. We learn about her childhood and how she grappled with identity throughout her life. We even visit her home in Iowa and get to know her family. The film keeps it light by smartly relying on their naturally funny tandem and the beautiful American country backdrop. It’s been said that to know the real American pulse, you’d have to go to the Midwest, and that’s exactly what they do. It’s not always pretty, but there are bubbles of joy there that present hope not just to Harper but to the many transpeople out there waiting to know if it’s finally time to head out (it is).

Genre: Comedy, Documentary

Actor: Colin Jost, Harper Steele, Kristen Wiig, Lorne Michaels, Molly Shannon, Paula Pell, Seth Meyers, Tim Meadows, Tina Fey, Will Ferrell, Will Forte

Director: Josh Greenbaum

Rating: R

Having an ordinary life isn't a bad thing, but it can feel like a huge disappointment, hearing of other people and characters having extraordinary lives. However, when Harvey Pekar started writing down that ordinary life, his life became… still quite ordinary, but at least with an outlet through his autobiographical comic book American Splendor. That being said, his biopic isn't quite ordinary, transforming Pekar’s eccentric musings into fourth-wall-breaking comic book panels, vignettes, and documentary-esque work, shifting between Pekar animated, acted by Paul Giamatti, and voiced occasionally by Pekar himself. And like his work, American Splendor resonates with the ordinary viewer, who, like him, just wants to try to make the best of life. It's pretty cool for someone that called himself a nobody.

Genre: Comedy, Drama

Actor: Daniel Tay, Donal Logue, Earl Billings, Ebon Moss-Bachrach, Hope Davis, James McCaffrey, James Urbaniak, Josh Hutcherson, Judah Friedlander, Madylin Sweeten, Maggie Moore, Molly Shannon, Paul Giamatti, Rae Sunshine Lee

Director: Robert Pulcini, Shari Springer Berman

Rating: R

Happiness is a difficult, disturbing watch. Unlike films that claim to be brave, Happiness actually goes there and shows us just how deep, dark, and perverse our urges can get. But far from being controversial for the sake of it, this fearless film has important things to say about the facade of happiness, the urgency of loneliness, and the futility of feigning ignorance about both. And it does so with an impressively wry humor delivered by a talented cast that includes Philip Seymour Hoffman, Lara Flynn Boyle, and Dylan Baker. They play their complicated characters so well, they'll have you thinking about the strange ways you can, in fact, relate to them on some level, long after the credits roll. 

This isn't a film you'll want to revisit often, but you will have to see it at least once in a lifetime—if anything, for the kind of painful honesty you’ll rarely find anywhere else.

Genre: Comedy, Drama

Actor: Ann Harada, Anne Bobby, Arthur J. Nascarella, Ben Gazzara, Bina Sharif, Camryn Manheim, Cynthia Stevenson, Dan Moran, Diane Tyler, Douglas McGrath, Dylan Baker, Elizabeth Ashley, Gerry Becker, Jane Adams, Jared Harris, Joe Lisi, Johann Carlo, Jon Lovitz, José Rabelo, Justin Elvin, Lara Flynn Boyle, Lisa Louise Langford, Louise Lasser, Marina Gayzidorskaya, Marla Maples, Matt Malloy, Molly Shannon, Philip Seymour Hoffman, Rufus Read, Socorro Santiago, Todd Solondz, Wai Ching Ho

Director: Todd Solondz

Rating: NC-17

Playing the lead in an addiction drama has long been shorthand for “I’m a serious actor,” but that’s not something Florence Pugh needs to convince us of, especially not when the drama is as contrived as A Good Person is. Though it has a solid foundation from which to explore worthy subjects — Pugh’s character Allison begins abusing painkillers after accidentally causing the death of two people in a car accident —  writer-director Zach Braff overstuffs the film with too many distractingly histrionic happenings for a compelling reflection on guilt and forgiveness to really emerge.

What’s more, any potential A Good Person has is squandered by the film’s frequent and bizarre tonal swerves from tearjerking sincerity to generational comedy, a jarring effect mimicked by the soundtrack’s wild veering from moody melodies to bright piano music in a single cut. Though Pugh does her customary excellent work here, she’s ultimately undermined by all the overlong, transparently manufactured, and downright whiplash-inducing melodrama around her.

Genre: Comedy, Drama

Actor: Alex Wolff, Brian Rojas, Celeste O'Connor, Chinaza Uche, Drew Gehling, Florence Pugh, Ignacio Diaz-Silverio, Jackie Hoffman, Jessie Mueller, Lauren Yaffe, Molly Shannon, Morgan Freeman, Nichelle Hines, Oli Green, Ryann Redmond, Sydney Morton, Toby Onwumere, Victor Cruz, Zoe Lister-Jones

Director: Zach Braff