The hosts report Ebert gave the movie one star and put it on his most hated list, which the hosts say was normally reserved for movies like Showgirls; it is called the all-time roughest Ebert moment.
The review is quoted: the film plays like an explosion at the screenplay factory, with a bewildered office boy rescuing pages at random that should have been mailed to the insurance company instead of filmed.
The review is called very well written but a horrendous take.
No defense is offered: Ebert mattered for film literacy, but with broad comedies he does not get why they work, like a basketball player who can't go left; Farley's weight at the center of the comedy may have made him sensitive. — Sean Fennessey
Fat guys need to stick together: Farley uses his weight to his advantage while doing cartwheels, the same reason for loving Kevin Duckworth and Oliver Miller.

Casting What-Ifs

Rob Lowe as Richard; Adam Sandler as Richard; Matthew McConaughey for the Lowe role; Roseanne Barr as Helen

In the discussion (4)

Approx. transcript time · 00:58:37Read transcript

As the hosts tell it, Michaels originally envisioned Farley with Lowe as the foil in the Richard part, which fell through because Lowe had other commitments.
The hosts say Farley pushed for Spade or Sandler; Sandler was already shooting Billy Madison, so Spade was the third choice, called the right one.
The hosts say scheduling conflicts nearly forced Lowe out, and quick auditions included Matthew McConaughey, which would have been fun between Dazed and Confused and A Time to Kill.
Helen the waitress was reportedly meant for Roseanne Barr, who was busy with her show; called a good miss.

Recasting Couch

Phoebe Cates in the Bo Derek role

In the discussion (5)

Approx. transcript time · 01:10:09Read transcript

Phoebe Cates replaces Bo Derek, a nostalgia pick echoing her Fast Times pool scene and a far better actress than Derek, called abysmal.
Without Bo Derek the '10' joke is lost.
Julie Warner had been written down but the size disparity is judged worth keeping.
A question is floated about swapping Julie Warner for 1995-era Julie Bowen after the Happy Gilmore episode.
Cates would have been only 32 in 1995, much closer to Tommy's age; agreed as a fair point.

Half-Assed Internet Research

Lowe uncredited; Farley's own stunts; Spade-Farley set altercation; Bo Derek's Razzie nomination; the pool actress dating both stars; alternate titles

In the discussion (6)

Approx. transcript time · 01:12:12Read transcript

The hosts report Lowe is uncredited; filming The Stand, he felt weird about another movie but did it because he loved Farley; Farley did his own stunts.
They relay Spade's story: after Spade drank with Lowe, a jealous Farley kept needling him, Spade threw a Diet Coke, Farley threw him against a wall and down stairs, and Spade walked off; they often communicated through the director.
Another version says Farley was too sick to go out, was upset when they went without him, and crushed Spade's tuna sandwich.
Bo Derek was reportedly nominated for a Razzie for Worst Supporting Actress.
The hosts say the woman in the pool was Lori Bagley, whom both Spade and Farley later dated, causing tension on Black Sheep.
They report the working title Billy the Third: A Midwestern was changed because of Billy Madison, with Fat Chance, XL and Rocky Road also considered; Tommy Boy is called the perfect name.

Picking Nits

Driving without a driver's door; unclear season; no background check on the fiancée; the fiancée's weight-camp grift; instant order hacking

In the discussion (5)

Approx. transcript time · 01:16:56Read transcript

Driving the highway without a driver's side door would be harder and scarier than shown.
The season is unclear: turning leaves versus convertible weather, when Farley would be far sweatier.
A rich Tommy Sr. should have run a background check on his fiancée; she met him at a weight-loss camp, an odd grift, and her son is only a few years younger.
Hacking Julie Warner's computer and changing hundreds of orders in a minute is implausible for a character who can't shoot out a tire.
It leads to a favorite moment where the chute rips Lowe's shirt off and he exits shirtless.

Probably Unanswerable Questions

Did Bo Derek's character kill Tommy Sr.?; Were Tommy and Michelle ever a couple?; How do their next six months play out?

In the discussion (4)

Approx. transcript time · 01:21:58Read transcript

Did Bo Derek's character kill Tommy Sr., who died at the wedding reception? A spiked drink or toxicology report reveal is suggested, and her ending up with Zelensky is bothersome.
Were Tommy and Julie Warner's character dating? They had one date, never kissed, and she nearly left him.
Asked about the next six months, a story follows about Jimmy's shelved ABC upfronts parody 'Fat Guy with a Beautiful Wife'; the couple could last. — Cousin Sal
The boat could last; love between the two is possible. — Sean Fennessey