Editorial Director, The Ringer
Chris Ryan
Chris Ryan is listed by The Ringer as editorial director.
Also referred to as Chris, CR, Christopher Ryan, Sierra
Stats
- Episodes credited in this archive
- 286
- Movies in this archive
- 271
- Attributed podcast choices
- 46
Recently watched on Letterboxd
Across the table
Appearing on these Rewatchables episodes
Good Will Hunting
1997 film
Bill Simmons · Ryen Russillo · Chris Ryan · Sean Fennessey
Aired April 1, 2025
Before Sunset
2004 film
Bill Simmons · Chris Ryan · Sean Fennessey · Mallory Rubin
Aired February 4, 2025
Mentioned in discussions
In the discussion (6)
- Clemenza is nominated.
- Sollozzo is nominated.
- Moe Greene is nominated and receives Chris’s vote.
- Jack Woltz is nominated and receives the other two votes.
- Luca Brasi is nominated but not considered a heat check. — Sean Fennessey
- Richard Castellano’s unusually brief film career and impact are discussed. — Bill Simmons
Most Rewatchable Scene
The garden conversation (two votes); the christening murders (one vote)
In the discussion (13)
- Sollozzo’s pitch to the family is nominated. — Bill Simmons
- Clemenza’s meatball lesson is nominated. — Bill Simmons
- Michael deciding to kill Sollozzo and McCluskey is nominated. — Bill Simmons
- The Louis restaurant assassination is nominated. — Bill Simmons
- Sonny’s tollbooth murder is nominated and debated.
- The Five Families meeting is nominated.
- Michael and Vito in the garden receives two votes. — Bill Simmons
- The christening murders receive Chris’s vote.
- The Las Vegas confrontation with Moe Greene is nominated.
- The opening undertaker audience is nominated.
- Sonny beating Carlo is nominated.
- Tom Hagen visiting Jack Woltz is nominated.
- The wedding is praised as an extended sequence.
Apex Mountain
No affirmative selection
In the discussion (5)
- Scheider’s Jaws breakthrough is defended as his career peak: a recognizable supporting star becomes a lead in the biggest movie. The case for All That Jazz cites an Oscar nomination, a signature late role and carrying the whole film; this prompts a distinction between career power and best performance. — Bill Simmons
- Shaw’s peak is disputed. A Man for All Seasons is called his best; From Russia with Love receives praise followed by a more reserved response. The Sting is praised repeatedly, while another response prefers Shaw in Jaws and points to Quint’s city-hands scene. — Chris Ryan
- Close Encounters leads the Dreyfuss choices. The unclear title transcribed as Mr. Hothotapus is loved but explicitly rejected as the answer. The Goodbye Girl is considered because of Oscar success while dismissed as a poor romantic comedy that nobody would revisit. His What About Bob performance receives praise. — Bill Simmons
- The debate explicitly distinguishes career power from best performance when defining Apex.
- All That Jazz is the preferred Scheider answer; the direct response explicitly identifies Chris as having long favored that film. — Chris Ryan
Most Rewatchable Scene
The nighttime boat sequence, Indianapolis speech and ending
In the discussion (9)
- The opening attack and the diving discovery of a head are honorable mentions. — Bill Simmons
- The beach attack, son mimicking his father, Indianapolis speech, Quint’s death and final shark confrontation are nominated. — Bill Simmons
- The wine visit is an additional favorite for the exhausted chief and the three-way domestic dynamic. — Chris Ryan
- The town meeting and first Quint appearance are nominated, with praise for the mayor’s scenes. — Sean Fennessey
- Chris Ryan chooses everything on the boat after sunset, including the Indianapolis speech. — Chris Ryan
- The Indianapolis speech authorship remains unresolved: playwright William Sackler [observed name] is credited with its premise, while Milius, Shaw and on-set rewriter Gottlieb are also discussed. — Sean Fennessey
- A reported failed intoxicated take was followed by an electrifying next-day performance. — Bill Simmons
- Shaw reportedly entered the casting discussion because the producers admired his work in The Sting. — Sean Fennessey
- The final stretch from Quint’s death through the shark’s defeat is a favorite, while the father-son scene remains a personal one-scene choice. — Bill Simmons
Apex Mountain
Tom Hanks; Gary Sinise; Robin Wright; Michael T. Williamson (as transcribed)
In the discussion (5)
- Tom Hanks with back-to-back Oscars makes the case. One host wonders whether it should be Castaway; the other argues this is his most commercial movie, won his second Oscar and cemented him as the alpha dog in Hollywood, the most bankable actor, who could make any movie he wanted, and it is probably his most iconic performance. A League of Their Own is preferred as funnier but conceded not to be an apex since he had not won an Oscar yet.
- Gary Sinise did ten seasons of CSI New York, and whether this can be topped is left as an open question. One host was never a giant Sinise fan, though he is really good here and creepy in Ransom in a way that made him dislike the man; he is also in The Green Mile, without many great performances, and the verdict is that this is definitely his Apex Mountain.
- Zemeckis is not a yes: Back to the Future, a hundred out of a hundred times. One host had forgotten Zemeckis made Back to the Future and calls himself a dumbass; Who Framed Roger Rabbit is loved and What Lies Beneath is underrated, though not in one household.
- Robin Wright is called her most complete performance with the most to do, unlike The Princess Bride where she is beautiful but barely on screen, and her career apex; the rejoinder is that she did not win the Oscar.
- Michael T. Williamson (as transcribed) is an absolute yes; he had a good hoop show on Showtime, and Chris Ryan only wanted to be on this episode to talk about his performance in Heat.
Biggest Oscar Travesty
Ethan Hawke losing Best Supporting Actor to Jim Broadbent in Iris
In the discussion (10)
- The new category is introduced as something these podcasts have circled before; it is expected to be really funny for a Roadhouse episode, with a case that Ben Gazzara was robbed in 1989 and for the Jeff Healy Band (as transcribed) for Best Original Song.
- 2001 was a dark Oscars: A Beautiful Mind won Best Picture over Gosford Park, In the Bedroom, Lord of the Rings and Moulin Rouge with no Training Day, and Ron Howard won Best Director over Ridley Scott for Black Hawk Down, Robert Altman for Gosford Park, Peter Jackson and David Lynch for Mulholland Drive, with no Antoine Fuqua.
- Several of those nominees are liked, In the Bedroom a lot and Gosford Park pretty good, but Fuqua and Training Day should have been nominated; Lord of the Rings was a tough hang that soaked up nominations for years in a way Star Wars never could, even though one host would take Star Wars a hundred times.
- Early validation from a nomination might have set Fuqua on a different course, since the movies he made after this resemble Training Day; Denzel's Best Actor win over Russell Crowe, Sean Penn in I Am Sam, Will Smith in Ali and Tom Wilkinson in In the Bedroom is fine, and Halle Berry won for Monsters Ball (as transcribed).
- Best Supporting Actor is the travesty that keeps one host up at night: the field was Ethan Hawke, Ben Kingsley in Sexy Beast, Ian McKellen in Lord of the Rings, Jon Voight in Ali for about three minutes, and Jim Broadbent in Iris, and Broadbent won.
- As in Rain Man, where Tom Cruise is the best person in the movie but Dustin Hoffman won, the performer who blows everyone away obscures how good the other one was; Hawke had to avoid being blown away by Denzel, be on PCP for half an hour and be believable in the fight scenes, which is likened to Chris Paul playing on a hamstring.
- Nobody here would pick Kingsley in Sexy Beast over Hawke, though he is good in it; two-hander movies like Butch and Sundance, The Sting, The Color of Money and Rain Man raise the question of how filmmakers present the straight man, and Redford is seen as more important than Hoffman in All the President's Men.
- Hawke is in more scenes and the movie starts in his house, so he could be argued as the lead with Denzel supporting, but really both were best actors, and doing it otherwise is like making Geena Davis supporting in Thelma and Louise.
- Later, on the phone, the Hawke loss to Jim Broadbent is called terrible and one of the few times an actor was right there with Denzel, alongside Viola in Fences, Morgan Freeman in Glory and Hanks in Philadelphia; he should have gotten that award.
- Earlier, the hosts note Denzel had only a supporting Oscar before this, having been passed over for Malcolm X, He Got Game, The Hurricane and Remember the Titans.
Unintentional Comedy Award
Lucas Haas; Leo's face when he wakes on the plane after limbo
In the discussion (2)
- Candidates were hard to find other than the movie writ large, or perhaps its coherence, though the host stresses liking the film; Lucas Haas is offered and welcomed as a very good choice.
- The look on Leo's face when he comes back from limbo on the plane resembles Chris Ryan in the Claytheism video (as transcribed) and is called hilarious.
In the discussion (7)
- Stallone cannot win because his Golden Globe speech failed to thank Coogler first, which may have cost him the Oscar; he seemed apologetic. — Bill Simmons
- Asked Coogler or Michael B, the answer is Coogler.
- Another goes with Coogler too: the movie could have gone wrong a hundred ways and he made it great, and with Black Panther this movie gets him the nod.
- Next, Stallone losing the Oscar to Mark Rylance is lamented, with a jab that Chris Ryan would respect Rylance; 'It has to be Ryan Coogler.'
- Black Panther would not happen this way without Creed being a great film people wanted to see. — Sean Fennessey
- A participant invited by name at the end, after being asked whether his mic is on, says Coogler won it for Stallone by reviving his acting career with a nomination and reviving the dead Rocky franchise, two victories; called the best take yet. — Wesley Morris
- Creed 2 is reportedly Creed against Drago's son, without Coogler. — Bill Simmons
Probably Unanswerable Questions
What actress plays Sean's wife in a flashback? How long did Will stay with Skylar, and what became of Will, Chucky, Casey Affleck's and Cole Hauser's characters? Why have Damon and Affleck not made another movie together, and why was Affleck not in Ocean's Eleven? Is this the best Boston movie of all time?
In the discussion (16)
- The block opens with the remake-as-series question, recorded separately.
- If there were a flashback with Robin Williams and his wife, what actress plays her: Deborah Winger (as transcribed) is offered; she has to look like a lifelong Boston lady; Amy Ryan from The Wire, Bonnie Bedelia, not Boston-y enough, and jokes of Conan O'Brien and Mark Wahlberg.
- How long did Will stay with Skylar, presuming he makes it to Stanford and finds her, which as a genius on early internet message boards he would: a semester, or three or four good weeks before it falls apart when they get drunk and she says you told me you didn't love me; Lambeau would have to be Will's reference since nobody else knows about him.
- What happens to these people: Will becomes an asshole hedge fund manager and Chucky becomes Matt Patricia, Sharpie in his hat, crunching tape for Belichick; or Will shows up, she is happy, they go to a Stanford party where a kid makes fun of his accent, Will beats the shit out of him and goes to jail, she bails him out and within three weeks they have broken up; twisted further, it becomes a prison movie, a shot caller situation where he joins a gang and, being a genius, figures out how to break out, Good Will Hunting 2 in jail in Palo Alto.
- Or he obviously becomes a tech billionaire, a Steve Jobs-ian figure in late-90s Northern California with a doctor wife-to-be and a difficult childhood; or he becomes Sean, a therapist, which one host refuses; or they realize it will not last, he goes back to Boston, Sean has died of a heart attack and he works construction, that friend; or 15 years later stories of his crimes and anger come out; or Chucky fulfills his promise to kill him and it becomes Face Off across Boston, Good Will Hunting 2: Hunting Will.
- What if Good Will Hunting 2 had been The Town, with Damon's life having failed; whether Affleck tried to convince Damon to take the Renner part is debated, and whether Damon can play that kind of crazy at all, since Talented Mr. Ripley was reactionary crazy, with the hosts directly challenging his acting.
- Why have these two not made another movie together: they went separate ways professionally, have a Showtime show coming that is basically a Wire for Boston, and the Fritz Peterson Yankees wife-swap movie fell through; Affleck has proven a great director and there is a great writer in Damon who should try again instead of The Great Wall; a theory that Affleck does not want to because Damon does not look cool anymore, or is mad he was cut out of Ocean's Eleven; whether Ben would have improved those movies in Casey's place or as the Andy Garcia role, though he needed to be older.
- Zach Mack (as transcribed) is asked which of the five sequels he liked most, picking Chris's; the prison pitch and Hunting Will are recalled, plus Will Hunting with a shotgun and a beard in 2018; if Skyler tells him to get lost in Palo Alto, does he spin out, become a custodian at Stanford waiting for her, which is creepy, or go Zuckerberg and create Facebook, you'll see, Erica Albright.
- The biggest criticism of the movie has been that it's not your fault is treated like a cure for abuse the film takes pains to establish, a guy putting cigarettes out on him, so that he hops in a car knowing how to love; if he is cured he is wealthy and with Skylar, if it moved too fast they break up after three weeks and he becomes a shot caller, still damaged and violent.
- Chucky now is 42 and leading or assistant foreman of his uncle's construction crew; Southie is much nicer and his crap house is worth five times as much, so he stayed or sold; maybe he took over the bar with Cole; Cole Hauser owns an auto shop and got murdered by an IRA customer, or was the muscle in a different Boston crew; Casey Affleck moved to LA to see Will, stayed, became a comedian and lives in the pool house; Will's friends came out within a year and it went badly.
- Asked how badly the visit went: Cole killed the guy, and they buried the body. — Shea Serrano
- The alternative is that the guys get arrested by TSA getting off the plane at LAX, too tanked, and are put on a jail plane back to Boston without seeing Will.
- Last question, probably answerable: is this the best Boston movie of all time; The Friends of Eddie Coyle is one host's favorite; another does not really care about Boston, having been three times without knowing Cambridge from Boston, and would rather watch The Departed; the qualifications for a city's signature movie are that it is awesome, uses the city, is authentic and could only have taken place there, like Rocky and Creed for Philly; the final three are The Departed, Good Will Hunting and The Verdict, with The Town fourth.
- Friends of Eddie Coyle is liked here too, with a sense one is being forgotten; the first hour of Social Network is a really good Boston movie. — Chris Ryan
- The Departed did not shoot much in Boston and Good Will Hunting shot a lot in Toronto, like Den of Thieves, set across LA but shot in Atlanta; the answer given is The Verdict, which uses the city best and has the authenticity, with Good Will Hunting very close, a 1A and 1B.
- Earlier, the film is called possibly the best Boston movie ever, on the short list, a discussion saved for later.
Apex Mountain
Andrew Keegan; Julia Stiles (one host puts this over Save the Last Dance; two name Save the Last Dance)
In the discussion (4)
- Asked whether this is anyone's apex, the first answer is a hedged 'I mean, I guess Andrew Keegan', which another turn firms up as both his heat check performance and his apex, congratulating him for going out on top.
- For Julia Stiles, two hosts call Save the Last Dance her apex, despite one taking issue with her dancing, while a third puts this film over Save the Last Dance.
- Stiles is outshined by Heath Ledger here, and Sean Patrick Harris (as transcribed) does not bring it the same way in Save the Last Dance; that film also features an unrecognizably different Kerry Washington, identifiable only by how she over-enunciates like Olivia Pope.
- Her later career is surveyed: Dexter as Lumen, the Borne (as transcribed) films that Chris Ryan would push for, The Prince and Me, the rough patch of Mona Lisa Smile and O, then Columbia and a return with State and Maine (as transcribed) and Silver Linings Playbook; she is very good at being mean.
Most Rewatchable Scene
The dam waterfall jump
In the discussion (8)
- The category opens by naming the aborted bus escape and train crash as about as fun a five minutes as an action movie gets, followed by a clip of Tommy Lee Jones taking over the investigation. — Bill Simmons
- Tommy Lee Jones's entrance is rated about as good as any, compared with Hopkins's Hannibal Lecter; he owns the movie from the moment he shows up. — Bill Simmons
- The nominees are the aborted bus escape and train crash, Tommy Lee Jones taking over the investigation, the dam waterfall jump, and the ending, called the big four. — Bill Simmons
- One participant goes with the dam: it is played realistically, with Ford visibly weighing a no-win jump, and it is called the best part of his performance, including the moment he puts down the gun. — Chris Ryan
- The dam scene contains 'I don't care', called maybe the best line in the movie and said to be ad-libbed by Tommy Lee Jones. — Andy Greenwald
- The early face-to-face meeting is praised as smart construction, followed by Gerard's orders to turn the dam off and a joke about the U.S. Marshals budget. — Andy Greenwald
- A second participant says they are with Chris and like the dam scene. — Andy Greenwald
- The third participant picks the bus escape and train crash, joking about the prisoners' silent plan, the bus flipping without deaths, the guards near retirement, and the guard who survives a toothbrush stabbing.
Flex picks
When I Would Have Died
Clearing gravel from the track
Flex pick · Chris Ryan
In the discussion (1)
- The death flex imagines being distracted while clearing gravel from the track rather than dying as a driver. — Bill Simmons
Flex pick · Chris Ryan
In the discussion (1)
- The Green Mill is identified during Rob’s breakup confession and selected for its prominent use in Thief. — Chris Ryan
Flex pick · Chris Ryan
In the discussion (1)
- An explicitly invited flex awards onscreen smoking to Pacino, especially smoking through heart problems. — Cousin Sal
The Neil McCauley “A Book about Metals” Award for Best Line from the Movie
The line that no camera was ever inside Truman’s head
Flex pick · Chris Ryan
In the discussion (2)
- The line that no camera was ever inside Truman’s head is selected for placing a limit on surveillance. — Chris Ryan
- The control-room exchange explaining that the show never depicts the couple’s intimacy is another favorite. — Glen Powell
Steven Seagal Hard to Kill Award: Did This Movie Need a Better Intimacy Coordinator?
Yes: Pamela Susan Shoop’s reported experience with an inadequately closed set and pressure for more nudity establishes the need.
Flex pick · Chris Ryan
In the discussion (1)
- Shoop reportedly expected a closed set, encountered many male crew members, and was protected by Debra Hill from pressure to perform full-frontal nudity. — Chris Ryan
“OK, Motherfucker” Award for When the Movie Goes Up a Notch
Loomis’s “you don’t know what death is” and the score kicking in
Flex pick · Chris Ryan
In the discussion (1)
- Loomis’s “you don’t know what death is” and the score kicking in mark the chosen step-up moment. — Chris Ryan
Picking Nits
Billie Jean may not need a love interest; a love-triangle revision is suggested.
Flex pick · Chris Ryan
In the discussion (2)
- Craig’s addressed contribution questions immediate romance with the first man she meets as weakening empowerment and preventing an exploration of fame’s loneliness. — Chris Ryan
- A revision gives Billie Jean prior history with Hubie and a triangle with Lloyd; his souvenir-store inheritance is mocked. — Bill Simmons
The Andy and Red – Zihuatanejo Award for What Happens the Next Day?
Modern celebrity speculation is followed by imagined futures for Lloyd, Binks, Hubie and Billie Jean.
Flex pick · Chris Ryan
In the discussion (6)
- In 2025 she might appear on the Hawk Tua podcast, join the Unwell network and release music; in 1985 she might return to Corpus Christi and become a schoolteacher. — Chris Ryan
- Lloyd is imagined entering VHS pornography with equipment, capital and experience of crime. — Bill Simmons
- Binks is imagined moving to Burlington, working at Ben & Jerry’s and getting beaten up after selling bad acid at a Dead show. — Chris Ryan
- Lloyd’s father is imagined with a minor role in the David Koresh standoff; Hubie becomes lieutenant governor, and Billie Jean faces lengthy copyright litigation. — Chris Ryan
- Hubie’s governorship and Binks becoming Doug McCray’s father in The Town are additional jokes. — Bill Simmons
- Hubie using the Billie Jean episode to claim he learned his lessons and launch a Texas political career is endorsed. — Bill Simmons
Mallory Rubin Award: Did This Movie Need a Better Sex Scene?
The flex proposes a missed Madsen–Sil sexual encounter, citing her visions and suggesting a triangle with Dr. Baker.
Flex pick · Chris Ryan
In the discussion (2)
- The flex proposes a missed Madsen–Sil sexual encounter, citing her visions and suggesting a triangle with Dr. Baker. — Chris Ryan
- Sil coming into bed while Marge is away is proposed; Madsen is imagined as the best mate and Molina as the hurried substitute. — Chris Ryan
Flex pick · Chris Ryan
In the discussion (2)
- Fitch is nominated for excessive autonomy, inadequate containment and killing plans, and hiring civilians instead of military specialists. — Chris Ryan
- Plainclothes special forces are proposed as a better response, and the absence of supervisory scrutiny is criticized.
The Den of Thieves Benihana Award for Scene-Stealing Location
Hog’s Breath Saloon
Flex pick · Chris Ryan
In the discussion (1)
- Hog’s Breath Saloon in Florida convincingly resembles a Massachusetts bar. — Chris Ryan
The Sean Penn “I Brought My Own Pack” Award for Excellence in On-Screen Smoking
Roy Scheider’s breakfast cigarettes
Flex pick · Chris Ryan
In the discussion (1)
- Scheider’s three cigarettes with coffee before breakfast are elite on-screen smoking. — Chris Ryan
From other episodes
Sourced picks from episodes not yet fully included in the archive.

The Neil McCauley “A Book about Metals” Award for Best Line from the Movie
Han Solo’s speech rejecting a mystical force controlling his destiny
Flex pick · Chris Ryan
Transcript excerpt · Targeted transcript check; recording not verified