The Rewatchables: ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey

Published 2024-01-30; 1:29:55 by the feed.

As extracted (engineer-sonnet-2026-10-13)

The extraction calls the show “The Rewatchables (The Ringer)” and the episode “'The Insider' With Bill Simmons, Chris Ryan, and Sean Fennessey”.

Hosts: Bill Simmons, Chris Ryan, Sean Fennessey. Guests: none.

Subject films: The Insider (1999).

On the transcript: Auto-transcript with no speaker labels and frequent name errors; recorded in 2019 as part of the Luminary 1999 series and re-run in 2024 on the 25th anniversary. Speaker attribution is low confidence throughout.

Added from the extractor's memory, not said

Film years other than those stated or implied in the episode were omitted rather than filled from memory.
Recorded in 2019 (inferred from references to 'this weekend when he wins the PGA' and 'the year of the Irishman'); episode metadata gives 2024-01-30 as the re-run date.

Awards and segments (62)

Most rewatchable scene

pick Lowell Bergman and Jeffrey Wigand in the car in the rain, feeling each other out (the Knicks small talk, the Tylenol story)
“Most rewatchable scene, Lowell and Jeffrey in the car feeling each other out while it's raining and Bergman being like, you think the Knicks are going to make the semifinals?”
Chris Ryan · 0:32:06
pick The lunch-table exposition scene where the 60 Minutes staff and lawyers lay out the Brown and Williamson legal defense
“Another great scene, the exposition scene where they're all eating lunch and talking about the legal defense that Brown and Williamson will put up.”
unknown · 0:33:57
floated The Mississippi court sequence, including Wigand staring into the Gulf
“The entire Mississippi court sequence.”
unknown · 0:36:07
floated Bergman discovering the CBS Westinghouse sale and confronting Hewitt and Wallace
“Bergman discovering the CBS Westinghouse sale and confronting Hewitt and Wallace”
unknown · 0:36:58
floated Wallace visiting Bergman at 5:30 in the morning to argue corporate responsibility
“I love the sequence where Wallace visits Pacino at 5.30 in the morning.”
unknown · 0:37:22
pick Don Hewitt and Bergman having it out at the end ("You fucked us")
“Well, on the flip side of that, the other rewatchable scene I have is when Don Hewitt and Bergman have it out at the end.”
unknown · 0:38:39
pick Wigand at the golf driving range, watched by the henchman with the smooth swing, then grabbing the 5 iron
“I have one more rewatchable scene that I just think is really well done and I like scenes like this just in general when he goes to play golf and the guys in the scene.”
unknown · 0:39:21
pick The Gulf shot and Bruce McGill's courtroom blowup ("wipe that smirk off your face")
“It has to be the Gulf and Bruce McGill.”
unknown · 0:41:07
pick Pacino unleashed: Bergman's blowup at Hewitt ("No, you fucked you"), chosen as the group's most rewatchable scene
“Let's give it to the Pacino unleashed as most rewatchable scene.”
Chris Ryan · 0:42:23

What's Aged the Best · The part of the movie that has gotten better with time.

nominee Al Pacino as Lowell Bergman
“I have Pacino's performance.”
unknown · 0:42:29
nominee Cinematography and the look and feel of the movie, including the Gulf shot
“I had the cinematography and the look and feel of the movie, like just the visual style.”
unknown · 0:45:14
nominee The inner workings of 60 Minutes and CBS News: Offered as both aged best and aged worst.
“I would say I have a nominee that's for what's age the best, which is also age the worst, which is the inner workings of 60 Minutes and CBS News and the corporate culture there.”
unknown · 0:45:25
winner Christopher Plummer as Mike Wallace: Plummer's Mike Wallace now reads as an interpretation, since Wallace is no longer on TV.
“Let's just give it to plumber.”
Chris Ryan · 0:50:31

What's Aged the Worst · The part of the movie that has aged badly.

pick The inner workings of 60 Minutes: Reads differently now given the chauvinistic behavior and the later CBS News troubles.
“I like I said, the inner workings of 60 minutes.”
Chris Ryan · 0:50:34
pick The slow-motion shot of Pacino walking down the street at the end
“The slow motion, Pacino leaving the going down the street and it slows down, like all of a sudden we're making a movie in 1981.”
Bill Simmons · 0:51:16
pick The score and Mann's strain for singularity
“I'm not a big fan of the score, as I mentioned.”
Sean Fennessey · 0:51:49
pick Wings Hauser as Brown and Williamson lawyer: Weird casting given where his career was; named as an aged-worst pick.
“Wingshauser is like prominently in this movie for 12 minutes.”
unknown · 0:52:41

Most 1999 Moment · The most 1999 thing in the movie.

pick Pacino and Crowe faxing back and forth
“I have Pacino and Crow faxing back and forth.”
unknown · 0:56:20
pick Pacino conducting business from payphones
“Just the sheer amount of business Pacino conducts from payphones.”
unknown · 0:56:27
pick Corporate influence on the news media as a live worry
“the thing that I was thinking of that hasn't aged that well is just the sort of general concern about corporate influence on the news media.”
unknown · 0:58:14
pick 60 Minutes mattering as much as it did
“I think just 60 minutes mattering like it did.”
unknown · 0:58:59
pick The acceptance of cigarettes in daily life
“just the acceptance of cigarettes in our lives.”
unknown · 0:59:20
pick The offhanded reference to Ken Starr
“The only other 99 thing I would mention is the offhanded reference to Ken Starr.”
unknown · 1:00:34

Casting What Ifs · Almost-castings and what ifs.

pick Val Kilmer: Kilmer was up for Wigand; Crowe showed what Kilmer's career could have been.
“Just Val Kilmer was up for Wygand”
Chris Ryan · 1:00:49
pick What if nobody had said to get Wings Hauser
“My biggest casting what if is what if somebody had never said, hey, we should get Wingshauser.”
unknown · 1:01:29

Dion Waiters Award · A small role with a big impact.

winner Bruce McGill: His one big scene, the Mississippi courtroom blowup.
“So I'm going to go McGill for Dion Waiters.”
Chris Ryan · 1:09:38
nominee Michael Gambon as Thomas Sandiford
“Michael Gambon.”
unknown · 1:09:17
nominee The golfing henchman
“I would also throw in the, uh, the amazing golfer, uh, henchman guy.”
unknown · 1:09:22
nominee Stephen Tobolowsky as Eric Kluster
“What about Stephen Tobolowski as CBS News President Coward, Eric Cluster?”
unknown · 1:09:30

Saul Rubinek Award · The best overacting.

winner Bruce McGill: Won on the strength of the "wipe that smirk off your face" courtroom scene; a double winner.
“He's also the winner of the Saul Rubin.”
unknown · 1:07:54
winner The three hosts' run of Knicks talk in the style of Pacino: A joke award to the hosts.
“They knew overacting award goes to the 3 of us for that run of Chino talking about the Knicks.”
unknown · 1:16:35

Joey Pants Award · The best that guy.

winner Bruce McGill: A triple crown with the Dion Waiters and Saul Rubinek awards.
“I like the idea of McGill winning the triple crown.”
unknown · 1:22:32
nominee Philip Baker Hall as Don Hewitt: Part of the longest nominee field the hosts say they have had.
“Philip Baker Hall, Gina Gershon, Stephen Tobolaski, Rip Thorne, Torn.”
unknown · 1:21:59
nominee Gina Gershon: Hosts split on buying her as a corporate lawyer.
“Philip Baker Hall, Gina Gershon, Stephen Tobolaski, Rip Thorne, Torn.”
unknown · 1:21:59
nominee Stephen Tobolowsky
“Philip Baker Hall, Gina Gershon, Stephen Tobolaski, Rip Thorne, Torn.”
unknown · 1:21:59
nominee Rip Torn
“Riptorn, kind of wasted in this movie.”
unknown · 1:22:06
nominee Michael Gambon
“Com Fiord, Debbie Mazar, Lindsay Krauss, Michael Gambon, and Esther Serrano as the FBI guy.”
unknown · 1:22:22
nominee Lindsay Crouse: Offered as the alternative winner to McGill.
“I do think Lindsay Krauss, a lot of people don't know what her name is.”
unknown · 1:22:35

Unintentional Comedy · Moments that are funny without meaning to be.

pick The golf driving range with two guys golfing in suits
“I had, uh, just the the golf driving range.”
unknown · 1:09:42
pick Gina Gershon
“I have Gina Gershon as a high powered corporate.”
unknown · 1:10:01
pick The hotel room wall melting to Wigand's kids on the beach
“I'm throwing in the scene when he's in the hotel room and he's staring in the wall and it, look, oh, and it melts?”
unknown · 1:10:42
pick Everyone in the movie is rich, so the stakes are hard to take seriously
“I think I think if you look closely at the movie, it's a little hard to take the emotional stakes as seriously because everybody in this movie is so rich.”
unknown · 1:11:01

Unanswerable Questions · Questions the movie leaves hanging.

pick How would this story have played in the internet era
“My big one was how would this have played in the internet era?”
unknown · 1:12:13

Picking Nits · Nitpicks of the movie.

pick Wigand's wife turns on him too fast
“the a nitpick is just, the wife was out on him pretty fast.”
unknown · 1:13:26
pick Mann's script says "semifinals" for the Knicks when anyone who follows sports would say conference finals
“Nobody's ever said semi-finals.”
unknown · 1:15:32

Best Quote · The best line in the movie.

pick Wigand: "Fuck it. Let's go to court.": Chris announces the category and names Wigand's line.
“Best quote.”
Chris Ryan · 1:16:40
pick Mike Wallace as Mike Wallace
“We work in the same corporation doesn't mean we work in the same profession.”
unknown · 1:17:48
pick Bergman: tell him to get on the phone
“Tell him to get on the fucking phone.”
unknown · 1:18:00
pick Hewitt and Bergman: "You fucked us" / "No, you fucked you"
“And then Hewitt, you fucked us.”
unknown · 1:18:37
pick Bergman to the FBI guy: "pissed off and curious"
“You better take a good look because I'm getting two things, pissed off and curious.”
unknown · 1:18:57
pick Wallace: "Fame has a 15 minute half life. Infamy lasts a little longer."
“infamy less a little longer.”
unknown · 1:19:36
pick Bergman: "I fought for you and I still fight for you"
“He's like, I fought for you and I still fight for you.”
unknown · 1:20:36

Apex Mountain · Where a performance or career sits on the mountain.

pick Al Pacino: Not for anybody; Pacino's apex is elsewhere.
“Is it Pacino's the Apex Mountain?”
unknown · 1:20:47
pick Russell Crowe: Crowe's apex is Gladiator, not this.
“I think crows is gladiator.”
unknown · 1:20:52
pick The golfing henchman
“The golfing henchman guy, definitely.”
unknown · 1:20:53
pick Christopher Plummer: Plummer's apex is The Sound of Music, not this.
“Yeah, sound of music.”
unknown · 1:21:14
pick Michael Mann: Floated as Mann's apex for getting this made; countered that Heat is his apex.
“Is this man's apex mountain just in terms of his ability to do”
unknown · 1:21:24

Sequel / Prequel / TV · The sequel, prequel or TV show they would make.

pick A 10-episode Netflix series
“Could this work as a 10 episode Netflix show in 2009?”
unknown · 1:22:47
pick A sequel where Wigand dates the Broadcast News lady
“Or a sequel where he, Jeffrey Wagan, starts dating the broadcast news lady.”
unknown · 1:23:10

Best Supporting Actor, 1999 Oscars · Who should have won or been nominated.

pick Christopher Plummer: Better than everyone but Jude Law; at least top five.
“I just feel like Plummer is better in this movie than basically everyone in that category”
unknown · 0:48:31
pick Al Pacino: Called outrageous that he was not nominated.
“Pacino, not nominated at all.”
unknown · 0:49:23

Who Won the Movie · Who came out ahead.

winner Al Pacino as Lowell Bergman
“Oh, unquestionably for me, Pacino.”
unknown · 1:25:15

Films that came up

Claims (49)

career (career): Al Pacino → Insomnia. Insomnia is the last Pacino movie that felt like an event before his decline.
“Last grasp, insomnia is the tail end, and then it flips.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:04:19 · Sean Fennessey (0.40 sure it was them)
career (career): Christopher Plummer → The Sound of Music. Plummer was the star of The Sound of Music, which they pick as his Apex Mountain.
“He was the star of the sound of music.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:07:00 · Chris Ryan (0.40 sure it was them)
career (career): The Insider → Heat. The Insider was Michael Mann's first film after Heat.
“It was man's 1st movie since heat.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:07 · Chris Ryan (0.50 sure it was them)
lineage (lineage): The Last of the Mohicans → Heat. Heat is described as the urban version of Last of the Mohicans, a step in Mann's progression toward The Insider.
“Then you've got heat, which in some ways is the urban version of Last of the Mohicans.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:22 · Chris Ryan (0.60 sure it was them)
craft (craft): The Insider → The Last of the Mohicans. The Insider is where Mann starts making wild formal decisions, after the romantic landscape painting of Mohicans and the urban Heat.
“And then Insider marks where man starts making all these really wild formal decisions.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:27 · Chris Ryan (0.60 sure it was them)
craft (craft): The Insider → The Last of the Mohicans. The same cinematographer, Dante Spinotti, shot both Mann films.
“Dante Spinati, who shot last night, he can shot. He also shoots the insider”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:38 · Chris Ryan (0.60 sure it was them)
craft (craft): Dante Spinotti → The Insider. Spinotti shoots most of the film handheld from someone's collar to visualize the characters' life-changing decisions.
“He also shoots the insider, but they're essentially trying to visualize what it's like for people to make decisions.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:40 · Chris Ryan (0.60 sure it was them)
verdict (verdict): Al Pacino → Any Given Sunday. Bill's favorite Pacino performance other than The Godfather is Any Given Sunday, which carries a terrible movie.
“My favorite pacino performance other than the godfather.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:09:21 · Bill Simmons (0.45 sure it was them)
career (career): Al Pacino → Scarface. Theory that Scarface broke Pacino by knocking him off his axis between over-the-top and nuanced.
“the theory of Pacino is that he was broken by Scarface”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:11:44 · Sean Fennessey (0.55 sure it was them)
verdict (verdict): Al Pacino → Sea of Love. Bill thinks it was Scarface, not Sea of Love, because Pacino is not doing that in Sea of Love.
“because if you watch Sea of Love, he's not doing that in Sea of Love.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:12:54 · Bill Simmons (0.55 sure it was them)
verdict (verdict): Al Pacino → Glengarry Glen Ross. Glengarry is a favorite of the 90s run because the specific material tempers Pacino's bigness.
“even something as well written as Glengarry, which is one of my favorite performances from this run.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:13:49 · Bill Simmons (0.40 sure it was them)
career (career): Al Pacino → Righteous Kill. Pacino's decline in event status ends with Righteous Kill with De Niro.
“And then ends up with righteous kill with De Niro in 2008”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:17:33 · Bill Simmons (0.50 sure it was them)
career (career): Russell Crowe → Al Pacino. Pacino gets three decades to be Al Pacino while Crowe gets five years, a statement about the movie business.
“Pacino gets 3 decades to be Al Pacino.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:18:33 · Chris Ryan (0.50 sure it was them)
career (career): Russell Crowe → Val Kilmer. Crowe's choice between character actor and leading man is likened to the Val Kilmer and Brad Pitt conundrum.
“This is the Val Kilmer Brad Pitt conundrum, right?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:19:07 · Bill Simmons (0.40 sure it was them)
lineage (lineage): The Insider → All the President's Men. The Insider is hoped to capture the same wave of reaction that All the President's Men did.
“they're hoping to capture that same kind of that wave that people have when they saw all the president's men.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:21:08 · Chris Ryan (0.45 sure it was them)
theme (theme): The Insider → JFK. JFK became the assassination movie though half of it is false, whereas The Insider really captures its specific moment with the cigarette industry.
“This movie really does capture this specific moment with the cigarette industry that played out with the lawsuits and everything.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:22:48 · Bill Simmons (0.50 sure it was them)
theme (theme): The Insider → The Blair Witch Project. Both are 1999 movies that could not happen a few years later because the internet changed things.
“I think that's a similar thing that just 4 years later, that movie doesn't happen.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:26:41 · Bill Simmons (0.45 sure it was them)
contrast (contrast): The Insider → Tangerine Dream. The Insider's operatic Dead Can Dance score departs from the synth sound Mann is famous for using.
“man's so famous for using like Tangerine Dream and these really evocative, synthy, beautiful sounds. And this has almost like an opera score.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:30:11 · Chris Ryan or Sean Fennessey (0.40 sure it was them)
lineage (lineage): Spotlight → All the President's Men. Spotlight was closer to the spirit of the conclusions of All the President's Men, if not its style.
“it was closer to the spirit of the conclusions of all the president's men, if not the style.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:30:39 · Sean Fennessey (0.40 sure it was them)
contrast (contrast): The Insider → Spotlight. Spotlight was a hit because it is a satisfying bad-guys-get-caught story, while The Insider is meditative and ambivalent.
“Spotlight is just like, let's get the bad guys with our reporting.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:30:52 · Sean Fennessey (0.40 sure it was them)
craft (craft): Thief → The Insider. The feeling-out scene between two good actors is a Mann staple, with Thief's the best.
“Crosby and Khan and Thief is the best one.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:33:01 · Chris Ryan (0.40 sure it was them)
people (people): Eric Roth → Forrest Gump. Roth is famed for clarifying a movie's problem inside one scene, as in Forrest Gump.
“Eric Roth, who is a co-writer of this movie, is famed for his ability to clarify the problem of a movie inside of one scene.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:34:49 · Chris Ryan (0.50 sure it was them)
craft (craft): Michael Mann → The Insider. Nobody likes a wide shot of water like Mann, first the Gulf with Crowe, then the ocean with Pacino.
“So good. Nobody likes to wide shadow water like Michael Mann.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:36:55 · Bill Simmons (0.40 sure it was them)
industry (industry): The Insider → Mike Wallace Is Here. The documentary on Wallace informs the Plummer scenes.
“And I think it actually informs this scene a lot”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:37:42 · Sean Fennessey (0.45 sure it was them)
lineage (lineage): Robert Redford → The Insider. The golf-range scene where the hero realizes he is followed is likened to a Redford footstep scene.
“That's the Redford, it's so good.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:39:53 · Bill Simmons (0.30 sure it was them)
craft (craft): Al Pacino → Heat. Pacino's patient, ulterior-motive conversational style is in Heat and in The Insider.
“he does it in heat too when he's trying to get something out of the other person”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:42:36 · Chris Ryan (0.40 sure it was them)
people (people): Al Pacino → Denzel Washington. Denzel is another actor who is great at being a screen partner, receiving and giving.
“That's a Denzel thing is very good at that too.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:44:02 · Sean Fennessey (0.35 sure it was them)
verdict (verdict): Michael Caine → The Cider House Rules. Caine won supporting actor for Cider House Rules after being passed over, a Susan Lucci situation.
“Susan Lucci thing.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:48:54 · Chris Ryan (0.40 sure it was them)
career (career): Christopher Plummer → Beginners. Plummer won his Oscar late for Beginners, given because of his long career.
“Christopher Plummer got that later on in his career for beginners.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:49:04 · Chris Ryan (0.40 sure it was them)
industry (industry): Sean Penn → Sweet and Lowdown. Penn was nominated for Sweet and Lowdown while Pacino was not nominated at all for The Insider.
“Sean Penn got nominated for sweet and low down.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:49:20 · Bill Simmons (0.40 sure it was them)
craft (craft): The Insider → Miami Vice. Mann's pop-abstract music choices, such as the Linkin Park and Jay-Z cues in Miami Vice, are a recurring misfire for some.
“Is this your, is this a subtle dig at Lincoln Park, Jay-Z being used in Miami Vice?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:52:07 · Sean Fennessey (0.35 sure it was them)
verdict (verdict): Michael Mann → Tangerine Dream. A speaker is not into Mann's Tangerine Dream soundtracks and thinks his pop-abstract music choices rarely work.
“It's one of the only things in his movies that I'm not like I'm not into those tangerine dream soundtracks.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:52:21 · Chris Ryan or Sean Fennessey (0.40 sure it was them)
career (career): Bruce McGill → Animal House. Bruce McGill will always be Animal House, but here he is moral certitude and lawyerly power.
“No, Bruce McGill is always going to be Animal House, you know?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:53:10 · Bill Simmons (0.35 sure it was them)
career (career): Wings Hauser → Tales from the Hood. The five films before The Insider for Hauser show where his career was.
“Tales from the Hood.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:53:52 · Sean Fennessey (0.30 sure it was them)
people (people): Diane Venora → Heat. Venora in The Insider is basically her sad Heat role again with long hair.
“but she's just doing a sequel to the heat.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:55:17 · Bill Simmons (0.40 sure it was them)
industry (industry): The Insider → Frontline (ESPN and the NFL). ESPN's Frontline-NFL episode was their version of corporate influence over news.
“Yeah, ESPN went through this with the frontline thing when they killed the NFL.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:58:31 · Bill Simmons (0.50 sure it was them)
what-if (what-if): Val Kilmer → The Insider. Val Kilmer was up for the Wigand role, a significant what-if.
“Just Val Kilmer was up for Wygand, which is pretty significant what if for this podcast”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:00:49 · Sean Fennessey (0.40 sure it was them)
what-if (what-if): The Insider → Thank You for Smoking. A punnier title like Thank You for Smoking would have told you what the movie was about.
“Like Jason Reitman's, thank you for not smoking.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:02:39 · Sean Fennessey (0.35 sure it was them)
what-if (what-if): The Insider → Erin Brockovich. Titles like A Civil Action and Erin Brockovich are cited in the title-brainstorm.
“Civil action is called.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:02:57 · Bill Simmons (0.30 sure it was them)
people (people): Michael Mann → Collateral. Mann loves a ham, someone just going for it, as in Collateral's Tom Cruise.
“He loves a ham.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:08:26 · Chris Ryan (0.35 sure it was them)
people (people): Michael Mann → Public Enemies. Mann loves people going for it across Ali and Public Enemies.
“And Ali, there's people just going for left and right, public enemies.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:08:30 · Chris Ryan (0.35 sure it was them)
career (career): Gina Gershon → Curb Your Enthusiasm. Gershon's Curb performance is rated a top-5 TV comedy performance, though not buying her as a corporate lawyer.
“Gershon's performance in Curb Your Enthusiasm is one of the top 5 TV comedy performances ever.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:10:30 · Bill Simmons (0.40 sure it was them)
theme (theme): The Insider → Pump Up the Volume. Smoking riffs: Christian Slater as a good screen smoker in Heathers and Pump Up the Volume.
“Christian Slater, really good smoker.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:12:51 · Chris Ryan (0.30 sure it was them)
career (career): Philip Baker Hall → Magnolia. Hall's 1999 includes Magnolia alongside this film.
“How about just his 99?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:20:14 · Bill Simmons (0.30 sure it was them)
career (career): Philip Baker Hall → Boogie Nights. Hall's run from 89 to 99 includes Midnight Run, Boogie Nights, Hard Eight and Seinfeld.
“Yeah, boogie nights?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:20:25 · Bill Simmons (0.30 sure it was them)
verdict (verdict): The Insider → Heat. Mann getting this movie made 34 years after Heat is called an achievement, though Heat with De Niro and Pacino is the true apex.
“And heat, he had De Niro and Pacino at a point when that still mattered and got like the best possible movie out of them.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:21:45 · Bill Simmons (0.40 sure it was them)
what-if (what-if): The Insider → Rage Against the Machine. A joke that the film would feel even more 1999 if Rage Against the Machine replaced Dead Can Dance on the soundtrack.
“To make it truly 99 feeling we replaced Dead can Dance with Rage Against the Machine on the soundtrack.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:23:01 · Unclear host (0.30 sure it was them)
what-if (what-if): The Insider → Broadcast News. Jokey sequel in which Wigand dates the Broadcast News lady.
“Or a sequel where he, Jeffrey Wagan, starts dating the broadcast news lady.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:23:10 · Chris Ryan (0.35 sure it was them)
career (career): The Insider → Any Given Sunday. Pacino did The Insider and Any Given Sunday in the same year.
“This in any given Sunday in the same year?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:25:21 · Chris Ryan (0.35 sure it was them)

Fun items (28)

fun, about Al Pacino: Pacino's hair in this movie is blown dry to perfection, like a White Snake video.
“he's right off the set of a white snake video, I think.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:03:49 · Bill Simmons (0.35 sure it was them)
fun, about Michael Mann: Mann shot the Mississippi, Louisville and the Middle East on location, taking Christopher Plummer to Israel for a 10 minute sequence.
“it's important for this 10 minute sequence that I take Christopher Plummer to Israel.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:04:48 · Chris Ryan (0.40 sure it was them)
fun, about The Insider: The Insider got seven Oscar nominations including picture, director, and adapted screenplay, and was swept by American Beauty.
“giving it 7 nominations, including pretty much all the big, heavy hitters, best picture best director, best adapted screenplay.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:05:53 · Chris Ryan (0.50 sure it was them)
fun, about Al Pacino: Pacino is in three late-90s dances with over-the-top; his Any Given Sunday inch-by-inch speech is called all time in a terrible movie, carrying it like LeBron.
“The Inch's speech is all time for me and that movie's terrible and he's carrying it like LeBron carried the 2007 caps.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:09:36 · Bill Simmons (0.50 sure it was them)
fun, about The Insider: The Insider was budgeted at 68 million and made about 29 million, felt like a bomb, and Joe Roth said selling it was like walking up a hill with a refrigerator on your back.
“when Joe Roth talked to the Times right before the insider came out, he said, uh, in regards to selling the movie to the public, he said it's like walking up a hill with a refrigerator on your back.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:29:14 · Chris Ryan (0.50 sure it was them)
fun, about The Insider: Most rewatchable scene nominees: the car feel-out in the rain, the lunch exposition table, the Gulf, the golf range, Wallace at 5:30 am, and Hewitt versus Bergman.
“Most rewatchable scene, Lowell and Jeffrey in the car feeling each other out while it's raining”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:32:06 · Chris Ryan (0.40 sure it was them)
fun, about Michael Mann: Gulf scene: Wigand staring at the water; joke that Joe Roth asked Mann to lose five minutes of golf and Mann refused.
“You think maybe we could just lose like 5 minutes of golf?”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:36:42 · Bill Simmons (0.40 sure it was them)
fun, about The Insider: The golf range scene: a henchman stares Wigand down after each swing until he grabs the 5 iron; the hosts rate the henchman a 9.5 swinger and Crowe a 4.
“Crow's like a four.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:40:27 · Bill Simmons (0.40 sure it was them)
fun, about Bruce McGill: Bruce McGill's courtroom outburst, 'Wipe that smirk off your face,' wins the Dion Waiters award and is a triple-crown candidate.
“This is not North Carolina, not South Carolina, nor Kentucky.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:41:19 · Bill Simmons (0.30 sure it was them)
fun, about Christopher Plummer: Plummer plays Mike Wallace not as an impression but as Plummer interpreting Wallace, with the pointing fingers and no prosthetics.
“he is just doing Christopher Plummer interpreting Mike Wallace.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:47:14 · Sean Fennessey (0.50 sure it was them)
fun, about Christopher Plummer: Plummer sips from a CBS Sports mug as a detail in the Wallace scene.
“he just like sits back and takes a sip out of a CBS sports mug.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:47:33 · Bill Simmons (0.40 sure it was them)
fun, about Al Pacino: Pacino was not nominated for The Insider, which the hosts call outrageous.
“Pacino, not nominated at all.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:49:23 · Bill Simmons (0.40 sure it was them)
fun, about Christopher Plummer: Plummer was born in 1929, nearly 70 in this movie, and won his Oscar at about 83 for Beginners.
“Christopher Plummer, never nominated for an Oscar before 2010.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:51:01 · Bill Simmons (0.40 sure it was them)
fun, about Michael Mann: Mann's slow-motion ending with Pacino walking down the street strikes Bill as tacky.
“The slow motion, Pacino leaving the going down the street and it slows down, like all of a sudden we're making a movie in 1981.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:51:16 · Bill Simmons (0.40 sure it was them)
fun, about Wings Hauser: Wings Hauser had five low-budget movies before The Insider and was Jonesy on 90210, a weird casting at that career moment.
“It was just a weird casting.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:52:47 · Sean Fennessey (0.35 sure it was them)
fun, about The Insider: Most 1999 moment: Pacino and Crowe faxing, payphones, and the New York Times in the lobby; plus the offhanded Ken Starr reference.
“I have Pacino and Crow faxing back and forth.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:56:20 · Sean Fennessey (0.35 sure it was them)
fun, about The Insider: Casting what-if: Val Kilmer was up for Wigand, and the hosts debate whether Crowe showed what Kilmer's career could have been.
“I think Russell Crowe showed what Val Comer's career could have been.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:01:06 · Chris Ryan (0.40 sure it was them)
fun, about The Insider: Title brainstorm: a better title might have been The Whistleblower or Cigarette Burns; Thank You for Smoking is cited as a title that tells you the subject.
“It just needed to have an element of danger to it.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:02:26 · Bill Simmons (0.40 sure it was them)
fun, about The Insider: The movie was originally called Man of the People; Roth and Mann wrote the first draft at the bar of the Broadway Deli in Santa Monica.
“Roth and Mann wrote the 1st draft of the screenplay at the Broadway deli in Santa Monica”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:03:02 · Sean Fennessey (0.40 sure it was them)
fun, about Mike Wallace: Mike Wallace detested the movie, and Don Hewitt criticized it in Page Six; Mann met Hewitt in the elevator of their shared building and Hewitt said 'that fucking Lil Bergman.'
“Hewitt had been criticizing the movie in page 6 throughout the production.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:03:57 · Sean Fennessey (0.40 sure it was them)
fun, about Michael Mann: Mann loves a ham: someone going for it, as in Ali, Public Enemies and Collateral's Cruise performance.
“He loves somebody just going for it.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:08:29 · Chris Ryan (0.35 sure it was them)
fun, about Gina Gershon: Gina Gershon cast as a corporate lawyer: some found it counterintuitive casting, others could not buy it.
“I liked it as counterintuitive casting.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:10:19 · Bill Simmons (0.30 sure it was them)
fun, about The Insider: The Knicks 'semifinals' line in the car scene draws a long riff on how nobody says semifinals; conference finals, since the Knicks were in the NBA finals that year.
“Nobody's ever said semi-finals.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:15:32 · Bill Simmons (0.40 sure it was them)
fun, about Pacino: They suggest a James Dolan biopic starring Al Pacino, who would play blues the whole time.
“They should, there should really, there should be a James Dolan biopic starring Al Pacino.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:16:10 · Bill Simmons (0.40 sure it was them)
fun, about The Insider: Best quote nominees: 'Try Mr. Wallace,' 'You fucked us / No, you fucked you,' and Wigand's 'Fuck it. Let's go to court.'
“Try Mr. Wallace.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:17:45 · Chris Ryan (0.30 sure it was them)
fun, about The Insider: Hewitt-Bergman 'fame has a 15 minute half life, infamy a little longer' is called a great line.
“fame has a 15 minute half life.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:19:31 · Chris Ryan (0.35 sure it was them)
fun, about The Insider: Apex Mountain: the golfing henchman, Bruce McGill and Plummer; Plummer's is probably The Sound of Music; Mann's apex may be getting this movie made 34 years after Heat.
“The golfing henchman guy, definitely.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:20:53 · Bill Simmons (0.30 sure it was them)
fun, about The Insider: Remake idea: as a 10 episode Netflix show with an episode just looking at the Gulf, plus swapping Dead Can Dance for Rage Against the Machine.
“To make it truly 99 feeling we replaced Dead can Dance with Rage Against the Machine on the soundtrack.”
The Rewatchables · ‘The Insider’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:23:01 · Chris Ryan (0.40 sure it was them)

Who's talking

Chris Ryan (host): Chris is the host of this installment and a Michael Mann devotee who frames the film's craft and context: the Pacino and Crowe careers, Mann's formal progression, the end of broadcast news dominance. He likes the exposition scene, Plummer and Pacino together, and the wild formal choices. He tends to read films through the movie business and what they say about their era.
Bill Simmons (host): Bill loves Pacino's swagger and Any Given Sunday, loves Heat, and treats the Michael Mann signature as a thing he can pick at, calling out the slow-motion ending and score as dated. He is a sports guy who can't let go of the Knicks 'semifinals' line, and he has little patience for stray bad casting like Wings Hauser. He is a sucker for scenery-chewers like Bruce McGill.
Sean Fennessey (host): Sean is the most film-critical of the three, with a theory of Pacino as broken by Scarface and an argument that The Insider is his most calibrated performance. He admires Plummer's non-impression of Wallace and values the Mann-Roth research. He is less into the score and the style when applied to a white-collar story.

The show's recurring bits

Apex Mountain: The moment a star peaks; where on the mountain a performance sits.
Who Won the Movie: The hosts name the person who came out of the film best off.
The Ebert review: Roger Ebert's original review and star rating read aloud. Ebert is cited, never on the show.
Casting what-ifs: Who was almost cast, or who should have been.
Most rewatchable scene: The scene each host would stop on while flipping channels.
Aged best / aged worst: What holds up and what does not.
Picking Nits: The little things in a film the hosts love that they don't think totally work: the nits.
Double feature: The film each host would pair it with; a programming pick.

Names the transcriber got wrong

'Sean Fantasy' / 'Sean Fantasy' = Sean Fennessey
'Wygan'/'Wygant'/'Wagan'/'Weigand' = Jeffrey Wigand
'Lil Bergman'/'Lowell Bergman' (real name Lowell)
'Krow' = Crowe
'Plumber'/'Palmer' = Plummer
'Wingshauser' = Wings Hauser
'Spinati' = Dante Spinotti
'Bruce McGogan'/'Bruce Weiggle' = Bruce McGill
'Dion Waiters award' and 'Saul Rubin' are recurring Rewatchables awards, partly mangled
'Joey Pants' award is a recurring award category
'Illuminary' = Luminary
'Rip Thorne' = Rip Torn
'Esther Serrano' = Esteban Serrano? uncertain
'Steve Tish' = Steve Tisch
'Lindsay Crass'/'Krauss' = Lindsay Crouse
'Brooks Katka' = Brooks Koepka
'Francesco Molinari' name as said
'Susan Zarinsky' = Susan Zirinsky
'Lincoln Park' = Linkin Park
'Hawk' (Denzel episode reference) possibly Chris Ryan's reference to a Rewatchables guest
'Gigli' transcribed 'Geli'
'Ayatola' scene: Pacino interviewing a hooded terrorist