Are we led to believe the woman falls for him when they break into the house at the end? Flagged for unanswerable questions.
Can you really leave diamonds in a fish tank without the chemicals harming them? It seems a stupid hiding place compared to a panel in the house.
A joke says Rosillo hides his diamonds, not in a fish tank; a reply says 'I keep mine on me at all times.'
Could the ending have had the federal agent help the man she loves escape instead of arresting him? Fast and Furious later did that.
A question for Bill Lawrence: why has no one nailed a prison sitcom? Oz is raised, and the answer offers to put a laugh track on an episode of Oz.

Roger Ebert's review

In the discussion (1)

Approx. transcript time · 00:47:04Read transcript

Roger Ebert gave the film three and a half stars and wrote that Clooney has never been better, that handsome young actors need miles before the full flavor emerges, and that Clooney at last looks like a big screen star.

Picking Nits

Back-and-forth chronology; fantasy set in the real hotel room; the report she couldn't have written; Foley going back for the maid; Ripley bragging about diamonds

In the discussion (9)

Approx. transcript time · 01:14:27Read transcript

Never seeing the scenes of Clooney's loyal buddy calling his sister, only hearing about them secondhand, is flagged as a picking-nits item.
The back-and-forth chronology was a little confusing on first viewing, though time stamps might have broken the flow.
Lopez's bathtub fantasy cheats by being set in the exact hotel, in the same color scheme, where Clooney and Rames are actually staying, though she has never been there.
A high-angle hotel shot after the Lompoc flashback signals the return to the present; the Mad Men fever dream is cited as a delicate case.
One speaker is anti-dream sequence and anti-narrator unless proven to work.
A nitpick read online: when did she write the report her boss is reading if she was unconscious after the crash?
Would Jack Foley really go back for the maid? He is fundamentally not a good guy, so the moment may not be earned.
Why would Albert Brooks's titan-of-industry character tell these guys about $5 million in diamonds?
Returning to the maid point: the movie takes pains to show Foley won't hurt anyone, knocking out the guard with a vase rather than killing him.

Casting What-Ifs

Sandra Bullock as Karen Sisco; Barry Sonnenfeld as director; Danny DeVito or Garry Shandling as Ripley

In the discussion (6)

Approx. transcript time · 01:18:47Read transcript

Sandra Bullock was supposed to play Karen Sisko; a quote from the director says she and Clooney had great chemistry but for the wrong movie, not Elmore Leonard energy, so they landed on Lopez; the pair later made Gravity.
The film was offered to Barry Sonafield first; he dropped out to do Men in Black, and his Get Shorty shows how different the tone would have been.
Luck matters: a different director can make a movie great, and Eddie Murphy almost got fired from 48 Hours.
Chemistry screen tests are explained as a last hurdle in couple-driven romantic comedies; rumor says Lopez's test was shot at Clooney's house, and TV shows sometimes rewrite when leads lack chemistry.
Danny Davidow and Garris Shandling were considered for Ripley; Shandling as Ripley is an intriguing what-if, though he might have glanced at the camera and needed a different edge for the office scene.
Shandling never found the right movie part; his Mike Nichols movie was a legendary disaster.

Recasting Couch

Laurence Fishburne as Daniel Burdon

In the discussion (2)

Approx. transcript time · 01:31:19Read transcript

Replace Lopez's boss, played by Wendell Harris, with Lawrence Fishburn, who would be formidable at the right point of his career.
The original actor is called the weakest in the movie despite having a lot of lines.

Half-Assed Internet Research

Ad-libbed dialogue; summer release; White Boy Bob callback

In the discussion (3)

Approx. transcript time · 01:32:00Read transcript

Per the commentary track with writer Scott Frank, cast members ad-libbed, including Cheeto's line about the high potentiality for the common motherfucker to bitch out.
Many in the industry felt the movie was mismarketed as a summer release when it should have come out in the fall.
Ving Rames tells White Boy Bob he likes to shoot his big mouth off, and later Bob literally shoots himself.