Hoffman would have been the pick years ago, but Cruise wins the movie, and not as a contrarian zag. — Bill Simmons
Another voice agrees and adds that the movie is Cruise's story of transformation, his first real adult part, pointing toward the rest of his career. — Bill Simmons
Barry Levinson is floated: Best Picture, Best Director and the number one movie, though nothing he made after is as good; he is rejected because people see it as a Hoffman-Cruise movie. — Sean Fennessey
Asked who from the last 20 years could pull off Charlie, Leo, Damon, Affleck, Chris Evans, Brad Pitt, E. McGregor, Michael Keaton and others are floated; Hanks would not be believable as a chain-smoking dick. — Bill Simmons
Pressed, the answer is Hoffman: Raymond became an iconic figure, won Best Actor and launched a wave of imitators; Hoffman is the not-overthinking-it answer, Levinson the overthinking one, and Cruise the smart answer. — Sean Fennessey
A voice says it really wants Cruise to win and feels bad; a reply says he'll be okay and jokes that he can't win the Oscar or Who Won the Movie. The count is not restated. — Sean Fennessey
The 1949 Buick Roadmaster is disallowed as too easy. — Bill Simmons
The pick is the 1984 uncut "top sheet" in Raymond's room, possibly 85; guesses at the cards include Ted Kluszewski, Reds, Sandberg, Clemens and Gooden. — Bill Simmons
Cruise's sunglasses: a great run that reinvented sunglasses in movies, the King of Raybans. — Bill Simmons
Tom Cruise: no for this movie, though a case is made for 1988; another view puts his peak at 1996 with Mission: Impossible, his first production, and McGuire. — Bill Simmons
Asked directly, the reply is "No, I think I'm going to go with" what a co-host is saying. — Chris Ryan
Hoffman's Apex is Kramer vs. Kramer, as decided on an earlier episode; Outbreak and Sphere are mentioned jokingly. — Bill Simmons
People's Court never got better: crushing it in the late 80s and prominently featured in the number one movie, part of the 4:30-6 p.m. TV block with Jeopardy and Wheel of Fortune. — Bill Simmons
Asked if he had heard of People's Court, the answer is vaguely; Judge Judy took it over. — Craig Horlbeck
Barry Levinson is a yes for this period: best director and the number one movie at the box office. — Bill Simmons
Levinson was also key to 30 for 30; once he committed, other directors followed. — Bill Simmons
Levinson pretty much invented modern TV with Homicide a couple of years later and has perhaps the most underrated behind-the-scenes career, though his filmography is called hit and miss. — Bill Simmons
Diner created a template everyone ripped off, and Levinson was already an Oscar-nominated screenwriter before that, having written ...And Justice for All in the 70s. — Bill Simmons
Kasdan is proposed as the winner of a most-underrated tournament; Grand Canyon is mocked.
Valeria Galena's Apex is Hot Shots.
Road-trip movies: no, though this is a great road-trip movie shot sequentially; a list follows: Easy Rider, Thelma & Louise, Almost Famous, Blues Brothers, Midnight Run, Planes, Trains and Automobiles, Smokey and the Bandit, Dumb and Dumber and Tommy Boy, with Road Trip, Vacation and Due Date added.
Handheld TVs, the Sony Watchman, were a thing for about three years. — Bill Simmons
Who's on First: not its Apex overall, but perhaps for the last 40 years. — Bill Simmons
The 1949 Buick Roadmaster and Qantas Airlines are yeses; Qantas is still throwing the no-hitter. — Bill Simmons
During filming Hoffman and Cruise called the movie two schmucks in a car and constantly worried it would not work. — Bill Simmons
Principal photography happened during the 1988 Writers Guild strike, so the final scene was apparently winged without writers. — Bill Simmons
The ending is questioned as unsatisfying for a Best Picture winner, since it lacks a sappy payoff where Raymond stays with Charlie. — Sean Fennessey
A sentimental Amtrak scene always lands for someone who spent the 80s riding Amtrak between a mom's house and a dad's house. — Sean Fennessey
Card counting is meant to be the climax that brings the brothers close and saves Charlie's business; the ending is neither victory nor defeat, and its ambiguity is liked. — Chris Ryan
Jokes imagine a modern version with Raymond as a Marvel superhero, a Wallbrook driveway epilogue, or Lenny killing Charlie.
Airline versions deleted the airline-accident scene, except on Qantas. — Bill Simmons
Choosing a flight at the airport and hopping on last minute was possible through the late 90s. — Bill Simmons
The film was written by Barry Morrow and Ronald Bass; Morrow created Raymond after meeting real-life savant Kim Peek. — Bill Simmons
Hoffman beat Gene Hackman for Best Actor and hugged him; they were playhouse classmates who shared Hackman's apartment on 2nd Avenue and 26th Street, where Hoffman slept on the kitchen floor before moving in with Robert Duvall on West 109th Street. — Bill Simmons
The three as roommates is pitched as a documentary or original series, compared to LeBron, Wade and Carmelo on one AAU team. — Bill Simmons
Asked whose career they would rather have, one voice picks Duvall and Hackman is picked as well; Hackman was the most liked by other actors; Denzel and Will Smith took movies to work with him. — Bill Simmons
Hackman won a second Oscar for a supporting part in Unforgiven, something Hoffman never did. — Bill Simmons
Duvall is picked as the best storyteller of the three, with Godfather and Apocalypse Now stories.
The Replacements is called a top-five Hackman performance, with scenes apparently done in one take. — Bill Simmons
Iris the hooker could have been a great one-scene part; Marky Post, described as having just passed away, is suggested with an 80s hairdo and a cocktail dress. — Bill Simmons
It was a lost scene, seemingly to save money, needing a hot 80s actress who could click with Cruise. — Bill Simmons
A joke category about which part a co-host wishes he could have played points to Lenny, who is close to Pantoliano's Midnight Run character.
Joey Pants as Lenny is called a much better recasting-couch answer than the earlier Iris pick, with a Guido the Killer Pimp reunion with Cruise; a voice then says "I changed my answer." — Bill Simmons
Tom dials it up with the whole Cruise overacting playbook; the car seller Lenny from the opening scene is also nominated. — Bill Simmons
Examples: the desert scene punching air and screaming, and the Missouri hotel-room ranting while waiting out the rain, cutting fish sticks in half to make eight. — Bill Simmons
CAA wanted Dustin Hoffman and Bill Murray, with Hoffman as Charlie; Murray went on to make What About Bob, called a similar but different-toned lane that suited him better. — Bill Simmons
CAA agent Paula Wagner, later Cruise's producing partner, suggested making Charlie the younger brother to get Tom Cruise in, raising objections that the two could never be brothers given the age gap. — Bill Simmons