5 Best Movies to Watch by Stephen Colbert

actor › Stephen Colbert
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, 2011

It might seem like a no-brainer that trying to make a comedy movie featuring a character with cancer is not a great idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. And then it might come as a surprise that this subtle attempt at cancer comedy comes courtesy of Superbad creators Seth Rogen and Evan Goldberg. It also stars indie cutie Joseph Gordon-Levitt as the young and fit Adam Lerner, who works as a writer for public radio before learning that he has malignant tumors all along his spine. Between his overbearing mum (Anjelica Huston), slightly obnoxious but good-hearted bestie (Seth Rogen), self-help groups, and his therapist (played by Anna Kendrick), he struggles to find a way of acquiescing to his 50/50 chance of survival. Similarly, 50/50 strikes a delicate balance between the bromance gags, the date-movie elements, and the grave subject matter at its heart. It manages to mine humor, pathos, and simple honesty from a dark situation, and is not afraid to “go there”. The result is truly compassionate comedy.

Genre: Comedy, Drama

Actor: Adrian Glynn McMorran, Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, Cameron K. Smith, Chilton Crane, Christopher De-Schuster, D.C. Douglas, Daniel Bacon, Donna Yamamoto, Jason Vaisvila, Jessica Parker Kennedy, Jonathan Levine, Joseph Gordon-Levitt, Laura Bertram, Lauren Miller, Luisa D'Oliveira, Marie Avgeropoulos, Matt Frewer, Matty Finochio, P. Lynn Johnson, Peter Kelamis, Philip Baker Hall, Sarah Smyth, Serge Houde, Seth Rogen, Stephanie Belding, Stephen Colbert, Sugar Lyn Beard, Tom MacNeill, Veena Sood, Will Reiser, William 'Big Sleeps' Stewart, Yee Jee Tso

Director: Jonathan Levine

Rating: R

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, 2023

Art is a hobby for most people, but for musician Jon Batiste and writer Suleika Jaouad, art is part and parcel of this thing called life. Of course, it’s part of their work, and it’s how they make a livelihood, but it’s more than that– it’s almost a spiritual ritual they cling to, especially when Jaouad finds out that her leukemia has returned. American Symphony mainly depicts the creation of said orchestral work, but director Matthew Heineman translates the symphony into cinematic form, culminating in a performance played over the intimate moments between Batiste and Jaouad. It’s not just a documentary of a performance, but a documentary about art, about creation despite life’s pains, perhaps to survive life’s pains. It’s a powerful work that makes it easy to believe in art as imperative for life, and vice versa.

Genre: Documentary, Music

Actor: Anna Wintour, Billie Eilish, James Taylor, Jon Batiste, Jonathan Dinklage, Justin Bieber, Lenny Kravitz, Louis Cato, Questlove, Simon Helberg, Stephen Colbert, Stevie Wonder, Suleika Jaouad, Trevor Noah

Director: Matthew Heineman

Rating: PG-13

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Shot from the movie

, 2016

Former Congressman Anthony Weiner just doesn’t give up. After a 2011 scandal that had him resign from office, Weiner tries to make a comeback in this documentary that follows his 2013 mayoral campaign. His passion for public service is indisputable, and despite his shortcomings, it’s hard not to root for his go-getter attempts at a second chance. To this end, he wins and fails, with each outcome feeling more dramatic and consequential than the last. Things culminate upon the revelation of a fresh, new scandal, which disrupts his unlikely rise as a top candidate as well as the film’s production flow, which then takes a turn for the better (or worse, depending on your sympathies for Weiner). 

Fast paced and brilliantly stitched, Weiner is a compelling account of a man who won’t back down, and of the people surrounding him who suffer from his obstinacy. The documentary is proof that even in our hypercritical age, it’s still possible to both humanize and criticize a “canceled” subject, all while maintaining level-headed humor and allure.  

Genre: Documentary, Drama

Actor: Anthony Weiner, Bill de Blasio, Donald Trump, Howard Stern, Huma Abedin, J. Buzz Von Ornsteiner, John Waters, Jon Stewart, Lawrence O'Donnell, Stephen Colbert

Director: Elyse Steinberg, Josh Kriegman

Rating: R

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Shot from the movie

, 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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, 2020

For those of us who don't lurk on internet message boards and participate in social media culture, a documentary about memes might seem frivolous. But Feels Good Man steers the conversation into one about semiotics: the way images become symbols and can continue transforming—from a harmless expression of the self, into a hateful banner for bigotry, into a cry of protest and freedom. As his Pepe the Frog creation takes on a life of its own, artist Matt Furie attempts to reclaim ownership of it and finds that the relationship between an artist and their own work can be as difficult as any toxic relationship. It's a bleak view of how unfeeling internet culture can be, but it reminds us that we always still have some power to beat the hate.

Genre: Comedy, Documentary

Actor: Adam Serwer, Alex Jones, Arthur Jones, Donald Trump, Donald Trump Jr., Emily Heller, Hillary Clinton, Johnny Ryan, Joy Reid, Katy Perry, Lisa Hanawalt, Logan Paul, Matt Furie, Melania Trump, Mike Majlak, Nicki Minaj, Phil McGraw, Rachel Maddow, Richard Spencer, Samantha Bee, Skinner, Stephen Colbert, Susan Blackmore

Director: Arthur Jones

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