Ebert gave the film two stars; one host had guessed he might go one and a half.
Ebert wrote that the more you think about what really happens in Cocktail, the more you realize how empty and fabricated it is; the hosts concede he is right.

Casting What-Ifs

Charlie Sheen; Robin Williams; Heather Graham; Molly Ringwald

In the discussion (5)

Approx. transcript time · 01:02:48Read transcript

The hosts say Charlie Sheen was considered for Brian Flanagan, which makes sense, and that Robin Williams also was, perhaps when the character was older.
IMDb suggests every white actor of the late 80s was considered; only Charlie Sheen is believed.
The hosts say Heather Graham was offered Jordan Mooney but declined because she was committed to License to Drive with Corey Haim.
Asked whether the movie is better with Shue or a young Heather Graham, the answer is that it is great with Shue, and another agrees.
The hosts say Molly Ringwald apparently turned down Jordan Mooney as well.

Recasting Couch

Casting left intact

In the discussion (3)

Approx. transcript time · 01:05:05Read transcript

The movie is called perfect and not to be touched.
Mel Gibson instead of Brown is floated, with an aside that he is not supposed to be talked about anymore.
The reply loves Brown here, calls it a favorite Brown movie, and says Gibson in a bar with Cruise would get Cruise glassed.

Half-Assed Internet Research

Bottle tossing added at Cruise's request; Kokomo nominations; flare bartending; Andrew Shue cameo; Scientology timing; brandy bet value; plastic bottles; cut darker yacht scene

In the discussion (8)

Approx. transcript time · 01:05:21Read transcript

The hosts say bottle tossing was added at Cruise's request.
The hosts say Kokomo was nominated for a Grammy and a Golden Globe.
The hosts say the bartending in the movie is called flare bartending, a real thing.
The hosts say there is an Andrew Shue cameo in the wedding scene at the end.
The hosts say that during filming Cruise was with Mimi Rogers, who was getting him into Scientology, and call this the movie that officially made him a Scientologist.
The hosts estimate the brandy bottle from the $500 bet at about $3,600 in 2020.
The hosts say plastic bottles were apparently given to Cruise because things kept breaking.
The hosts say the trailer shows part of an extended, darker final yacht meeting that has Doug claiming a move on Jordan; it was cut, which may explain Brian's revenge with Kelly Lynch.

Picking Nits

Coughlin at TGI Fridays; sleeping with Coral over a $50 bet; missing Jamaica savings; Cruise's Jamaica makeup; Jordan's deli job; the father's buyout amount; Coughlin's lucid suicide note

In the discussion (9)

Approx. transcript time · 01:11:00Read transcript

Why Coughlin worked at TGI Fridays: he was hiding, just out of jail, or pushed out of a bar venture; the last is favored.
Coughlin sleeping with Coral and having her make out with him to win a $50 bet is monstrous; the two keep chasing each other's partners.
After about three years in Jamaica, Flanagan should have had about $70,000; a reply says Jamaica was seductive but not the money machine he expected.
Cruise appears to wear heavy makeup in Jamaica, perhaps covering a sunburn, with a Couples Retreat comparison.
Why Jordan worked in a deli when she was only cut off later, and why her apartment is so nice, go unanswered.
The father's $10,000 buyout is too low; $75,000, the bar money, would have been the right number and a better ending.
Flanagan is called a scumbag in answer to whether he would take $25,000. — Bill Simmons
The number one nitpick is Coughlin, barely conscious, leaving a lucid, thoughtful suicide note within about an hour.
Answers include that it is a bad movie with chopped-up New York scenes, that Coughlin might have been murdered, and that he had pre-written the note after already deciding.

Probably Unanswerable Questions

Cell Block as a business; elapsed time; why Coughlin was killed off instead of spun off

In the discussion (7)

Approx. transcript time · 01:18:51Read transcript

Did Cell Block work as a business? It would get hot and be out of business in about nine months.
Cell Block needed a tiger cage to become one of Stefon's bars. — Sean Fennessey
How much time passes is unclear; guessed at five years, though Uncle Pat's regulars look unchanged.
Why kill off Coughlin rather than spin him into a sitcom? Titles include Cocktails and Dreams, Coughlin's Law, Coughlin and Grace, Coughlin's Corner, and the favored "Coughlin!" with an exclamation point.
The Coughlin sitcom would be set back home in Perth, Australia. — Chris Ryan
Earlier possibly-unanswerable question: was that the first time Cruise heard Addicted to Love?
Earlier question flagged for this segment: how did Coughlin know where Flanagan was for his honeymoon?