The hosts report that Britney Murphy was originally lined up to play Mary, taken to be the Anna Pacoan role, and it fell through; she might have fit Rosario Dawson's role instead.
The hosts report that Toby McGuire bought the rights to the novel and was supposed to star, then chose Spider-Man and stayed on as a producer.
The movie is judged not as good with McGuire as Monty, though he is called a dark horse who can surprise.
Favorite McGuire performances named include Brothers with Jake Gyllenhaal, Spider-Man 2 for its reaction shots in action scenes, and the first 40 minutes of Spider-Man 3; Ice Storm is called his best movie.
The Ice Storm is described by a host as one of the great movies about whiteness made by a non-white filmmaker, with James Shamish writing and Engley directing; a future Ice Storm episode is promised.

The Russian gangster role, with an unnamed better actor

In the discussion (4)

Approx. transcript time · 01:25:43Read transcript

The actor playing the Russian gangster did not work for one participant.
Spike Lee could have called De Niro, Pacino, Kytel or Pesci, but that is walked back since the role is a Russian gangster.
The Malcovich-in-Rounders path is fun but distracting, and the film wants focus on what it cares about, in keeping with its restraint.
Even so, a better actor would have been the choice; no actor is named.

Skipped: research already shared

In the discussion (1)

Approx. transcript time · 01:26:51Read transcript

Half-assed internet research is passed over because it was all given already during the episode.

Whether the beating helps Monty in prison

In the discussion (2)

Approx. transcript time · 01:30:57Read transcript

The only nit: would being made ugly really help Monty in prison? It is called dubious.
A counter-reading is that he wanted to be punished by someone he knew because he was upset at letting his life slip away; that reading is found convincing.

Matt Damon in the Barry Pepper role; the Hoffman character's Monday; whether Monty's girlfriend waits; her job

In the discussion (7)

Approx. transcript time · 01:32:34Read transcript

Is the movie better with Matt Damon in the Barry Pepper part? Reasons: whether he would be better, whether it is a fun new role for him, and whether a Rounders-reunion cast with Norton, Hoffman and Spike Lee raises its Oscar ceiling; this is asked while liking Pepper.
A reply: Damon changes the stakes and would require fleshing the character out more; Pepper became a better actor as the decade went on.
Another view: it is probably a longer movie but taken more seriously as an awards movie because of the names.
Pepper's career is reviewed, with his run ending after this period; playing a role in Battlefield Earth alongside Travolta is called a red flag, but he is called a good actor and great in this movie.
What is the Hoffman character's Monday like? Awkward, probably handing in his resignation.
Will Rosario Dawson's character be waiting when Monty gets out in seven years? The answer is no, she is long gone, and the dad is probably dead.
What is her job? It is unclear; maybe a waitress, maybe a student, since she was 17 when they met, the same age as the Anna Pacquin character.