At some point in the past five years I realized that listening to podcasts has replaced watching TV or movies for me. Though I still watch the occasional video entertainment, usually via streaming on Netflix or Amazon Prime, I more often turn to podcasts for amusement and edification when the workday is done.

My relationship to podcasts predates the notion of podcasting, and probably goes back to the early 2000s, when I used to stream This American Life episodes over my dialup connection when I was living in Thailand and writing Vagabonding. By the early 2010s, when I got my first smartphone, I added podcasts like Longform, Studio 360, The Tim Ferriss Show and Scriptnotes to my rotation – and these days I probably listen to episodes from two-dozen podcast franchises from month to month.

Though I listen to different podcasts for different reasons, my go-to favorite for the past year or so has been The Rewatchables, a movie podcast produced by Bill Simmons’ sports/pop-culture website The Ringer. Each episode of The Rewatchables features Simmons and assorted cohosts analyzing a movie that has, over the years, inspired multiple re-watchings. Unlike more formal film-criticism podcasts (like, say, Filmspotting or Unspooled), The Rewatchables is delightfully laid-back. It takes its movies seriously – obsessively, even – but less in the manner of earnest culture-critics than of obsessive, exuberant pals who happen to be fans of the movie in question.

I first discovered The Rewatchables through its Silence of the Lambs episode (see #4 below), and I was taken by the podcast’s mix of personal and objective insights – the way the hosts were unashamedly autobiographical in detailing their love for the movie, even as they shared universal insights about what made the movie great. Though each Rewatchables conversation encompasses all of the tangents and callbacks of movie-fan exuberance, it also grounds its analysis in categories (including best quotes, most rewatchable scenes, and what’s aged the best/worst) that stay the same from week to week.

I’ve come to enjoy The Rewatchables so much that it has influenced my own podcast, Deviate, which has featured movies in a number of episodes this season, including two – Do the Right Thing with Wesley Morris and Kicking & Screaming with Michael Weinreb – where I’ve more or less poached Ringer contributors for my own cinematic conversations.

Since The Rewatchables recently hit its 100-episode landmark, I wanted to itemize my Top-Five favorite episodes so far. As with the podcast itself, my own favorites are pegged to movies I already love. That naturally leaves out episodes about films I’m not familiar with (like, say, Proof of Life or Varsity Blues) – but my Top-Five list hinges on episodes’ insights and enthusiasms more so than my own affection for the movies themselves (which means that episodes about The Big Lebowski, The Social Network, and Remember the Titans – movies I love – don’t quite make this list).


1) Dead Poets Society


This episode exploring the 1989 Robin Williams private-school/coming-of-age drama is a classic – if for no other reason than the fact that Bill Simmons, Chris Ryan, and (the always great) Mallory Rubin give heartfelt shout-outs to real-life teachers who inspired them when they were growing up. Simmons points out how Dead Poets Society is, in its own way, a kind of “sports movie for English majors,” since it’s about a group of young people coming together to explore collective passions and achieve common goals.

In general, the podcast conversation underscores how important that phase in one’s young life can be – and it unpacks the nuances of teaching, parenting, and youth, and how the movie approaches each. It also has a hilarious tangent speculating about which positions the various characters would play on a soccer team (based on a scene where Williams and the young actors play a game after class).

I discussed Dead Poets Society in Season One of my own podcast – specifically in the “Why 1980s coming-of-age movies matter” episode featuring author Kevin Smokler. Among other things, I confessed that the reason why Walt Whitman features so prominently in my first book Vagabonding has a lot to do with the fact Whitman’s poetry plays a significant role in the movie (which first caught my attention when I was an 18-year-old high school senior).


2) Dazed and Confused


Rewatchables stalwarts Chris Ryan and Sean Fennessey help Simmons unpack this 1993 Richard Linklater high school picaresque (which I also explored in my own episode about teen movies). There are so many great insights here about the contradictions, idiosyncrasies, and brutal truths of teen life – including an interesting riff about how important car-cruising was for young people in the days before cable-TV and VHS tapes. The hosts praise the performances of many of the young actors in Dazed and Confused – though Simmons in particular has harsh words for young Wiley Wiggins’ (lack of) baseball skills.

A significant tangent of the conversation is given over to the iconic sequence when Matthew McConahey’s Wooderson walks into a pool hall in slow motion to the strains of Bob Dylan’s “Hurricane.” Simmons notes how, were it him walking into a pool hall in his own imagination, it would be scored by The Doors’ “LA Woman“; Fennessey says his song would be Black Rob’s “Can I Live“; Ryan imagines Wu-Tang’s “Cash Rules Everything Around Me.” As I listened to this podcast episode, I couldn’t help but think my dream entrance-song would have been Van Halen’s “Unchained.”


3) Reality Bites


Of all the movies on this list, Reality Bites is the only one that I have not come to love – and in fact I’m pretty sure I saw it just once, in the theater, in 1994. I thought the movie was fine, but I was ambivalent about its characters, and it felt a little too on-the-nose in its “Generation X” marketing. What makes this podcast conversation terrific, however, is the presence of the always-insightful pop-culture commentator Chuck Klosterman, who helps Simmons unpack the Generation X motifs of the movie – particularly the notion of “selling out,” and how this was a genuine anxiety for many young people in the 1990s.

The hosts also point out how, in that last pre-internet era, young people bonded over their shared consumption of common movies, TV shows, sports, and music – and while they admit that Reality Bites was a Gen-X classic (along with Singles and Before Sunrise), they assert that Noah Baumbach’s Kicking and Screaming was a superior movie. As someone who has explored Kicking and Screaming with Ringer writer Michael Weinreb on my own podcast, I would absolutely love to hear Simmons and Klosterman break down Baumbach’s debut movie on some future episode of The Rewatchables.


4) The Silence of the Lambs


This discussion of the 1991 Anthony Hopkins/Jodie Foster movie is what first turned me on to The Rewatchables – in part because Bill Simmons and Chris Ryan aren’t afraid to talk about the movie as respectful, gung-ho fans (as opposed to analytical, straight-laced critics).

Specifically, I love Simmons’ fixation with Ted Levine’s depiction of the Buffalo Bill/Jame Gumb character, and how, when the movie first came out, his portrayal achieved a singular vibe of unsettling horror and unsettling hilarity for many viewers. Simmons and Ryan are also astute in describing the way director Jonathan Demme sneaks in narrative exposition by having the viewer learn things through Foster’s astute-yet-vulnerable Clarice Starling character.


5) The Shawshank Redemption


I love The Shawshank Redemption so much that I’ve taught its strengths as a Stephen King adaptation in my annual Paris Writing Workshop – and it was also the subject of my own podcast episode, featuring screenwriter and film-professor Kathy Van Cleve. The Rewatchables‘ take on this movie features Simmons and Ryan, but also – delightfully – Simmons’ father William, who first recommended the movie to Bill when it was in theaters back in 1994.

Together, their conversation speaks to the pure charismatic power of Shawshank‘s story and characters (even as the hosts take issue with certain unrealistic details of Tim Robbins’ prison escape). At one point Simmons calls it “the most rewatchable movie of all time,” and I’m tempted to agree. I’m not sure that it’s the greatest movie of all time, necessarily, but it is certainly a pleasure to rewatch.


Note: I don’t host a “comments” section, but I’m happy to hear your thoughts via my Contact page. To learn more about what this blog is all about, read items #2 and #3 from my update post.