It comes down to Chappelle or Buscemi, though Buscemi may not have been in enough of the movie, even if he probably does qualify; an argument is made for Swamp Thing, who does a nice job in just a few scenes, funny and a little charming despite being the wildly racist Aryan Brotherhood prisoner, and one host would hang out with him.
Asked who they picked for the heat check, the answer is Chappelle, who was great and incredible in what is almost a nothing part with no real role in the movie; the objection that you cannot pick Chappelle because of the racism material is met with the point that he only did the one line, and the pick stands.
The Sally Can't Dance character; losing Chappelle at 43 minutes; Cusack's hair and air of being above the movie; the prison guard's Current Affair, Hard Copy and Geraldo references; the guitar solo after the God line; the insulin subplot; Johnny 23
The Sally Can't Dance character is rough and not great; they probably would have cut it now, and even in the late 90s it was awkward and weird rather than something 1997 audiences thought was good.
Getting rid of Chappelle at 43 minutes has aged the worst; Chappelle could have helped the last two thirds, so cut somebody else and keep Pinball, the funny guy. The guess is they only had him for about three days, that he came up with his own dialogue, and that they did not know what they had.
Cusack's hair hurts: this is the first time it was going back as the 90s went along, like his best friend Piven, and he shows up with a flowing mane that flies around like a huge Trump wig in the convertible scenes. One host feels the movie is beneath him the whole time, an undertone of not believing his agent told him to do it, while another loves Cusack and places this right around Grosse Pointe Blank.
In Cusack's defense, Rosenberg wrote the parts for Cusack and Buscemi with them in mind; Colm Meaney's character even uses 'loquacious', and they are all idiots compared to Cusack, who is the one person in the movie, in sandals, who could have been you while everybody else is a superhero.
The gregarious, hilarious prison guard on the plane, a David Tao type (as transcribed), has aged the worst with his line about seeing eleven Current Affairs, two Hard Copies and a genuine Geraldo interviewee, shows that are all long gone. Also the cheesy guitar solo that kicks in when Cage, told by Bubba Gump that there is no God, declares that he will show God exists, after which Cage walks through a gunshot to the left arm without flinching.
The insulin subplot has aged poorly: there is no need for the diabetic shock the entire movie, since Cage could simply stay for Rachel Tickatin (as transcribed), who would be jumped by Johnny 23. Michael T. Williamson (as transcribed), whom a host really likes, spends the film shouting for his insulin, including 'get off my insulin' during the riot, and a secret favorite moment is Cage's weary 'Jesus' when Williamson gets shot.
Earlier, while picking nits, a host had meant to save the secretly armed DEA agent for aged worst: he pulled the Fredo Corleone, grabbed the gun, sweated and seemed out of control.
Johnny 23 has also aged the worst, though arguably it was aging badly even as the movie came out.
Malkovich saying the title in the movie, two different times, is a favorite thing and the hallmark of Bruckheimer movies, like 'welcome to the Rock'; the hosts imagine Bruckheimer reading the script in the bathtub and jotting a note that nobody says the title.
Nick Cage has aged the best: he has become a punching bag, but people forget he won an Oscar and was an awesome action hero in the 90s, holding the Grantland action-hero championship belt for two or three years; unlike 80s action guys such as Stallone, Schwarzenegger and Seagal, he, Bruce Willis and Mel Gibson were actors before they were action heroes, and he rattles off post-murder one-liners like the bunny line.
The secret of the movie is that ridiculous things happen but the characters are played by smart, good actors buying in: Cusack, Malkovich, Ving, Buscemi and Cage are all great, and Malkovich is 100% evil, believing everything he is saying.
Cage's hair has aged the best, this being the best year for it: thinning, so he grew it out wavy, with no explanation for going from high and tight out of the army to an outrageous mullet in prison while bettering himself and learning Spanish, looking like a bass tech for Poison.
Chappelle has aged incredibly well, and there is more racially charged humor than remembered, which one host flatly labels racist, including a lot of characters using a slur for each other; Chappelle is nonetheless very funny. The Cyrus kill line 'Cy... anara' (transcribed 'Sigh! Anatta'), which he had prepared and was waiting for someone to call him Cy, is another thing that aged best.
The Buscemi and Cage exchange after Cage comes back up from the kill below is played as a clip: whether working 50 hours a week for 50 years and hoping to die before the indignity of the toilet is insane. Buscemi goes to nine other levels, 'most murders are a crime of necessity rather than desire', and would give the greatest TED talk; a host admits that movies mocking people for having a job hurt his feelings, as with Heat.
Malkovich has aged the best for this host, on his run of villains like In the Line of Fire, really in the pocket as the heavy, funny, smart and scary, knowing exactly how far to go; it was a great period when action movies stopped requiring jacked-up Jose Canseco types and instead hired incredible drama actors to elevate stupid material for less money than the action guys cost. — Chris Ryan
The trend started with Rickman in Die Hard and led to Lithgow and Malkovich; asked which Malkovich role comes to mind first, the answers are In the Line of Fire, Dangerous Liaisons and Teddy KGB, with Con Air right underneath; he looks the same in every movie yet his characters feel different, as in the Killing Fields, and Mile 22 gets a thumbs up with reservations.
A young Michael K. Williams could have played Mel; Trejo would have been fun hanging out at the Emporium, someone who knew Wooderson; Buscemi could have been one of the coaches, the offensive coordinator reading the letter.
The easy quick answer is Buscemi, but Michael K. Williams should not be slept on: there is not a lot of diversity in the movie and he could have been dropped into any poker scene, or played Grandma (as transcribed), or even Worm, which leads to the idea of Black Rounders.
Black Rounders, a Ringer Films presentation, would be incredible, with Williams as Worm, though he is probably too old, so it goes back to the drawing board; both settle on Buscemi, who fits at the Taj table or the Chesterfield as a New York guy.
Honestly all three could work, but Buscemi is the pick as very Buscemi-esque; rather than Walken's part he could have played the priest, which is agreed to be good.
Steve Buscemi for sure: he could have had the Paul Giamatti part or played the wedding caterer, since there are a lot of small roles for him to pop up in.
The evolution of the Danny Trejo category is said to be one of the six or seven things that matter most to Bill; Steve Buscemi is one of the added names and could definitely be in this movie, in the Estevez role rather than Krieger's, with a joke that he should be Claire; Trejo himself is never placed.
