The Rewatchables: ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey

Published 2019-01-15; 1:15:15 by the feed.

As extracted (engineer-sonnet-2026-10-13)

The extraction calls the show “The Rewatchables (The Ringer)” and the episode “'Old School' With Bill Simmons, Chris Ryan, and Sean Fennessey”.

Hosts: Bill Simmons, Chris Ryan, Sean Fennessey. Guests: none.

Subject films: Old School (2003).

On the transcript: No speaker labels and heavy ASR errors; sponsor reads (Proper Cloth) and the Godfather corrections segment are included in the timestamps. Speaker attributions are mostly inferred by context and are low confidence.

Awards and segments (64)

Most rewatchable scene

pick Frank the Tank at Metropalooza, ending with the streaking and the ladies driving it, through to Frank coming back to life
“going Frank the Tank.”
Bill Simmons · 0:20:25
floated Blowjob class
“Blowjob class.”
Bill Simmons · 0:16:56
floated The whole Darkgun birthday party, including the regifted bread maker
“Dark gun birthday party.”
Bill Simmons · 0:17:00
floated Blue dies during the KY wrestling match, possibly running into Blue's funeral and Will Ferrell singing
“And then blue dies during a KY wrestling match.”
Bill Simmons · 0:17:14
pick The first meeting in the kitchen at Luke Wilson's new place: earmuffs, and Vince Vaughn walking around with a hockey stick destroying things
“go with the hockey stick scene.”
Chris Ryan · 0:20:20
pick The earmuffs conversation with Luke Wilson, the most iconic thing in the movie aside from "we're going streaking"
“go earmuffs along with Chris.”
Sean Fennessey · 0:23:02
floated The first time we meet Jeremy Piven's character, the dean ("Cheese")
“I really like the 1st time we meet Jeremy Piven's character.”
unknown · 0:18:16
floated The opening setup: Luke Wilson goes home to Juliet Lewis and the blindfolded people in the bathroom
“I really like, uh, even just the opening setup with going home to Juliet Lewis and she's got 2 people in the bathroom”
unknown · 0:18:45
floated Vince Vaughn watching his commercial and mouthing along to it
“There's so many other good ones like Vince Vaughan watching his commercial and mouthing along to it.”
Sean Fennessey · 0:21:45
floated Will Ferrell working on the car and talking to her about restrictor plate off
“The scene where, um, Will Ferrell's working on the car and he's talking to her about restrictor plate off.”
Sean Fennessey · 0:21:51
floated The wedding at the beginning, Vince Vaughn muttering as the bride walks up the aisle
“I was going to say the same thing about the, um, uh, the wedding in the beginning.”
unknown · 0:22:05
floated Luke Wilson meeting Ellen Pompeo for the first time, drunk ("Sunshine State, gorgeous")
“Luke Wilson meeting Ellen Pompeo for the 1st time and he's drunk and he's like, Denver.”
unknown · 0:22:45

Roger Ebert · Reading Roger Ebert's review of the movie.

pick Old School: Ebert panned it and said there is so little humor; no star rating is given. The hosts say he is never to be trusted on comedies.
“He panned old school. He said, I avoid altogether the question of old school's veracity and move on to its humor, which is easy to master because there's so little of it.”
Bill Simmons · 0:14:58

What's Aged the Best · What in the movie holds up best today.

pick Luke Wilson getting frisked at TSA and disrobing, set to Ryan Adams' To Be Young: Likely the first time he remembers anyone having fun with post-9/11 airport security.
“Luke Wilson getting frisked at TSA and just disrobing?”
Bill Simmons · 0:24:19
pick Ellen Pompeo as Nicole: Seeing her as the cute lady Luke Wilson has a crush on, before Grey's Anatomy; it feels jarring.
“Who is about to become one of the biggest and most bankable TV stars of the last 40 years, but in this movie is just the cute lady that Luke Wilson has a crush on?”
Bill Simmons · 0:24:44
pick The Dan Band at the wedding: The wedding band's swearing and the reaction shots of Will Ferrell and Perrey Reeves.
“But the damn band was just great.”
unknown · 0:26:18
pick Snoop Dogg: A good snapshot of a moment in Snoop time.
“Snoop Dogg's age really well.”
unknown · 0:27:45
pick Craig Kilborn: The sensation of seeing Kilborn in the movie; he also shows up under aged-worst.
“I think the sensation of seeing Kilbert. I mean, it's like, oh, fuck. Kilbert's in this movie.”
Bill Simmons · 0:28:54
pick The closing credits that tell story, with Kilborn's crash: About two and a half minutes of story in the credits; the hosts tie it to Todd Phillips mastering the form in The Hangover.
“Great closing credits in this movie have aged the best.”
unknown · 0:30:10
pick The soundtrack, with Here I Go Again played four times
“And I mean, here I go again, I think, is played 4 times.”
Bill Simmons · 0:31:48
pick Luke Wilson as Mitch: He calls this and The Royal Tenenbaums the alpha and the omega of Luke Wilson; a longer Luke Wilson argument gets saved for unanswerable questions.
“This and Tennenbaums are the two, that's the alpha and the omega of Luke Wilson.”
Chris Ryan · 0:32:10
pick Will Ferrell as Frank the Tank: The movie launched him toward being his favorite comedy star of the century.
“I mean, it obviously literally launches Will Ferrell to become probably my favorite comedy star of the century?”
Sean Fennessey · 0:32:28
winner "Earmuffs": People still say it and it is part of conversation; Bill had predicted earmuffs would win. The hosts add "You're my boy, Blue" to the lexicon later.
“I would say earmuffs is age the best.”
Sean Fennessey · 0:32:41
pick Patrick Cranshaw as Blue: "You're my boy, Blue" is in the lexicon along with earmuffs.
“Because you're my boy Blue, along with earmuffs, is in the lexicon.”
unknown · 0:53:03

What's Aged the Worst · What in the movie plays worst today.

winner Elisha Cuthbert as Darcie: She is in high school and sleeps with Luke Wilson's character; the hosts say 17 or 18, either way not great.
“Well, in this case, it would be Elisha Cuthbert's character aging the least, I think. I had her at the top of the list.”
Bill Simmons · 0:33:29
nominee Craig Kilborn: His acting.
“Kilburn's acting?”
unknown · 0:33:39
nominee Jeremy Piven's toupee
“Piven's toupee?”
unknown · 0:33:42
nominee Artie Lange: A misuse of Artie Lange, playing it completely serious.
“It's a misuse of Artie Lang.”
unknown · 0:33:51
nominee James Carville: Aged badly two ways: why is he in it, and 16 years later younger people do not know who he is.
“It's aged the worst 2 different ways.”
unknown · 0:34:23
nominee Brian Callen's agent: Added tongue in cheek because his career should have been bigger.
“I'm adding to what's age the worst, Brian Cowen's agent.”
unknown · 0:38:54

Casting What-Ifs · Almost-castings and recasts.

pick No casting what-ifs: the movie was written for Vince Vaughn and there is no oral history: The hosts find no drama or near-misses; the only what-if is the unmade sequel script.
“They wrote it for Vaughn.”
Bill Simmons · 0:36:12

Dion Waiters Award · Biggest heat check of the movie, a small part that scores big.

nominee Craig Kilborn: Put in because Bill thinks Kilborn thought it was a heat check.
“I'm putting Craig Kilburn in there just because I think he thinks it was a heat check.”
Bill Simmons · 0:36:51
winner Juliet Lewis as Heidi: Only in two scenes, one of them in the closing credits; Sean also votes Juliet Lewis.
“I have Juliet Lewis as the winner.”
Bill Simmons · 0:38:08
nominee The Dan Band
“Um, the Dan band.”
unknown · 0:37:15
nominee Seann William Scott as Peppers: As the animal trainer with the goat.
“Sean Williams Scott.”
unknown · 0:37:23
nominee Brian Callen as Greek waiter
“One other nominee is Brian Callen playing like the Greek waiter in the diner when he comes over and he's like, it is on me, Godfather.”
unknown · 0:38:17
nominee Terry O'Quinn: Raised and dismissed as not really a Dion Waiters since he is only in two scenes.
“What about Terry O Quinn?”
unknown · 0:39:00
winner Juliet Lewis as Heidi
“I'll go Juliet Lewis too.”
Sean Fennessey · 0:39:31

Apex Mountain · Where a person's career peak sits relative to this movie.

pick Craig Kilborn: Apex as the first season of Kilborn on The Daily Show; another host says Kilborn probably thinks this movie was his apex.
“I think 1st year Daily Show was what I would go for.”
unknown · 0:46:15
pick Will Ferrell: Not this movie; making Anchorman and having it succeed, a movie-career apex.
“Having that movie succeed, which is it's insane.”
unknown · 0:46:50
pick Vince Vaughn: One host says this movie and the Dodgeball and Wedding Crashers run; another picks Wedding Crashers, when he was one of the biggest stars we have.
“I'm gonna go wedding crashers, which I think was a year later.”
unknown · 0:47:22
pick Luke Wilson: The mainstream run from Legally Blonde to Charlie's Angels to this, when he was getting lead roles; leads into the Harrison Ford argument.
“I think so, because it's right around here is the run for him that is actually like the mainstream run where it's like legally blonde to Charlie's Angels, this.”
unknown · 0:47:48
pick Elisha Cuthbert: 24 season one era; this feels about as good as it got.
“It feels like this is about as good as it got.”
unknown · 0:50:52
pick Patrick Cranshaw as Blue: He went out high.
“He went out high.”
unknown · 0:52:50

Joey Pants Award · Best that guy: a far-background player who went on to be recognizable.

winner Patrick Fischler as Jeremy Piven's henchman: The guy from Mad Men, also in Mulholland Drive; once named the host says that is how you win the Joey Pants Award.
“That's how you win the Joey Pants Award, and I have no idea what your name is.”
unknown · 0:54:31
nominee Patrick Adams as the guitar player during Dust in the Wind: A far background player who is now the star of Suits.
“Patrick Adams, who plays guitar during Dust in the Wind, is the star of Suits.”
unknown · 0:53:46

Saul Rubinek Award · Best overacting in the movie.

winner Andy Dick as Gordon Pritchard: Out of his mind in his one scene.
“I'm gonna go Andy Dicker.”
unknown · 0:55:16
nominee Seann William Scott
“Don't sleep on Sean Williams Scott really going for it.”
unknown · 0:55:18
nominee Will Ferrell as Frank the Tank: "We're going streaking" at the top of his lungs, and the cinder blocks speech.
“We're going streaking at the top of his lungs is pretty, pretty Rubeneck-esque.”
unknown · 0:55:37

Picking Nits · Nitpicks of a film they love.

pick Ellen Pompeo's character touching Luke Wilson's after a string of red flags: The biggest flaw of the movie; the counterpoint is she has bad taste in men.
“There's like 9 different times she should have been running.”
unknown · 0:56:03
pick Vince Vaughn's Beanie not cheating: They have to zip it up so he stays within normal behavior and is not evil, though the scene where he pulls back is well acted.
“Why wouldn't Vince Vaughn be a cheater?”
unknown · 0:57:10
pick The back-to-school competition plot in the last act: It starts to become too much like Back to School, a conflict scene Animal House started.
“One of the flaws of the movie, I think, is when it starts to become too much like back to school, you know, where there's like a competition element to it.”
unknown · 0:34:32

Best Quote · Best line in the movie.

winner "Blue, you're my boy": The memorable quote other than earmuffs.
“Best quote comes down to Blue year, my boy.”
unknown · 0:57:48
winner "Earmuffs" and the cockballs exchange
“All I got to do is say earmuffs to him.”
unknown · 0:58:10
nominee Mitch's wedding toast about the early flight home from San Diego
“I do love the entire toast speech at the wedding.”
unknown · 0:58:35
nominee Beanie: "Columbus wasn't looking for America"
“Well, Columbus wasn't looking for America, my man, but that turned out pretty okay for everyone.”
unknown · 1:02:03
nominee "I know a great sand guy"
“I also really like, I know a great sand guy.”
unknown · 1:02:22

Unanswerable Questions · Open what-if questions about the movie.

pick Who is the 2019 Craig Kilborn cast in the stunt role? Floated: Logan Paul, Joe Buck, Gus Johnson, Jim Nantz, Mark Jackson, Jeff Van Gundy, Trevor Noah; settled on Jalen Rose: Hosts agree it has to be a famous non-actor, likely from sports TV.
“Who's the 2019 Craig Kilborn who would have been cast in old school if it came out in 2019?”
Bill Simmons · 1:02:34
pick Jalen Rose
“It's Jalen Rose.”
unknown · 1:03:39
pick Could they have improved on Luke Wilson (Owen Wilson was floated)?: Chris argues Luke Wilson could have been Harrison Ford with action-movie shape; Sean, Chris and Bill mostly wouldn't change him.
“Could they have improved the Luke Wilson spot?”
Bill Simmons · 1:03:52

Who Won the Movie · Who came out on top because of this movie.

winner Todd Phillips: Argues Phillips is bigger than Apatow, with a Joker movie next and a possible Oscar nomination for A Star Is Born as producer.
“So my vote is Todd Phillips.”
Sean Fennessey · 1:07:32
winner Vince Vaughn: Picked for variety; every line he has is quotable.
“I'm going to go Vince Vaughan just for variety.”
Chris Ryan · 1:07:34
winner Will Ferrell
“I'm going with Ferrell. There's a Will Ferrell comedy run.”
Bill Simmons · 1:07:45

Al Martino Award · The worst actor in the movie, a Godfather-podcast running award.

winner Craig Kilborn: Done during the Godfather follow-up segment at the end.
“The worst actor in old school.”
Bill Simmons · 1:13:22

Films that came up

Claims (50)

career (career comparison): Will Ferrell → Mike Myers. Ferrell tried Myers' playbook of turning an SNL character into a movie, but never got his Wayne's World.
“He tried to take a character from the show and make a movie out of it, and that was not successful.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:03:49 · Sean Fennessey (0.40 sure it was them)
career (career launch): Old School → Will Ferrell. The film launches Ferrell as a movie lead and became the template for all his later characters.
“this character kind of is the template for all the characters he would play in a movie”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:03:59 · Chris Ryan (0.55 sure it was them)
lineage (character origin): Will Ferrell → Old School. Frank the Tank is an extension of his SNL Dodge Stratus guy, the suburban insanity of domesticity.
“Frank the Tank is kind of the Dodge Stratus extension.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:04:35 · Chris Ryan (0.50 sure it was them)
theme (same-era run): Old School → Wedding Crashers. Old School starts the R-rated comedy boom that runs through Wedding Crashers, Superbad, Step Brothers, and The Hangover.
“This sets off an era from 03 all the way through, and the R-rated comedy boom”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:04:50 · Sean Fennessey (0.50 sure it was them)
lineage (genre lineage): Old School → Animal House. Old School is the latest in a frat-movie cycle that returns every 10 to 15 years, starting with Animal House.
“It is in keeping with the kind of every 10 to 15 years frat movie that we now get.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:05:23 · Bill Simmons (0.40 sure it was them)
lineage (filmmaker lineage): Old School → Ivan Reitman. Phillips and Armstrong's movie owes a lot to Ivan Reitman's 80s comedies; it is their son.
“it owes a lot to the Ivan Reitman comedies of the 80s.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:05:45 · Chris Ryan (0.50 sure it was them)
lineage (genre lineage): Old School → Stripes. Old School sits in the Animal House-to-early-80s run of comedy plus nudity that includes Stripes.
“there is a run, basically, that starts with Animal House and goes all the way.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:06:03 · Bill Simmons (0.40 sure it was them)
unmapped (meta-commentary on 80s comedies): Old School → Pineapple Express. Old School and the Apatow-era movies after it are meta commentaries on earlier comedies; Pineapple Express is that generation's Midnight Run or 48 Hrs.
“they're basically trying to make their version of Midnight Run or 48 hours or those kinds of action comedies, thriller comedies from the 80s”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:07:02 · Sean Fennessey (0.50 sure it was them)
contrast (era contrast): Old School → Adam Sandler. Old School has a maturity and more ideas than the earlier silly Sandler/Carrey era, despite being juvenile.
“Old school has like a maturity to it, even though it's really juvenile”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:29 · Chris Ryan (0.40 sure it was them)
unmapped (groundwork): Old School → There's Something About Mary. Farrelly brothers hits like Mary laid the ground for Road Trip and the R-rated wave.
“All of those kind of laid the ground for, uh, road trip.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:08:55 · Sean Fennessey (0.40 sure it was them)
people (same director groundwork): Old School → Road Trip. Road Trip, Phillips' first narrative film, laid groundwork for the R-rated run; it is set at an upstate New York college like Old School.
“Todd Phillips's 1st movie. First narrative movie.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:09:00 · Sean Fennessey (0.40 sure it was them)
lineage (creator precursor): Frat House → Old School. Phillips' frat documentary is a template for the movie.
“Frat House, which is this really interesting kind of template for the movie that we're going to talk about.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:09:56 · Sean Fennessey (0.50 sure it was them)
career (career obsession): Todd Phillips → Project X. Phillips' recurring subject is how young men, and later aging men, mess up, running from Frat House through Project X to The Hangover.
“he has an obsession with young, how young men fuck up”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:10:17 · Chris Ryan (0.40 sure it was them)
theme (persona comparison): Vince Vaughn → Bill Murray. In his comedies Vaughn is basically playing himself as a smart-ass, like Bill Murray.
“he's basically doing the Bill Murray thing.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:12:41 · Sean Fennessey (0.40 sure it was them)
career (career echo): Vince Vaughn → Swingers. Old School comes back to the Swingers energy after years of odd roles, including the Psycho remake.
“I think this is the funniest I've ever found him.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:12:53 · Bill Simmons (0.50 sure it was them)
lineage (remake trend): Starsky & Hutch → The Dukes of Hazzard. TV remakes started well with Brady Bunch and Addams Family but failed as pure comedies later.
“Those movies didn't work as well because they were trying to just make them pure comedies”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:14:09 · Chris Ryan (0.45 sure it was them)
career (career run): Will Ferrell → Anchorman: The Legend of Ron Burgundy. Old School, Elf, and Anchorman are Ferrell's back-to-back-to-back three-movie run.
“So Pharaoh rips off old school Elf Anchorman, just back to back to back.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:15:48 · Bill Simmons (0.50 sure it was them)
contrast (role inversion): Jeremy Piven → PCU. Piven subverts his PCU older-flunky character by playing the dean.
“he's kind of like subverting his PCU character.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:18:24 · Sean Fennessey (0.40 sure it was them)
contrast (role contrast): Juliet Lewis → Natural Born Killers. Lewis was previously known as a killer in Natural Born Killers; Old School is her first real comedy.
“I feel like this is her 1st real comedy.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:19:47 · Chris Ryan (0.40 sure it was them)
craft (soundtrack): Old School → Ryan Adams. The film opens on Ryan Adams' 'To Be Young', a great way to start.
“Set to one of the best songs literally of all time, Ryan Adams, to be young”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:24:34 · Bill Simmons (0.45 sure it was them)
career (career perspective): Ellen Pompeo → Old School. Pompeo is a cute crush here, shortly before becoming one of TV's most bankable stars.
“Who is about to become one of the biggest and most bankable TV stars of the last 40 years”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:24:44 · Bill Simmons (0.50 sure it was them)
people (recurring cameo): The Hangover → The Dan Band. The Dan Band also appear in The Hangover and other Phillips movies.
“they're in the hangover, too.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:27:02 · Sean Fennessey (0.40 sure it was them)
career (career): Dan → Dumplin'. The leader of The Dan Band, seen at the Old School wedding, also co-wrote one of the songs in Dumplin'.
“So the guy, Dan, who's the leader of the band, co-wrote one of the songs in Dumplin, the Netflix movie? Oh, this year? Yeah, so he's also like kind of a songwriter on the low.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:27:33 · Chris Ryan or Sean Fennessey (0.35 sure it was them)
people (cast overlap): Old School → Starsky & Hutch. Snoop Dogg's Old School performance was supposedly a trade-off to get him into Starsky & Hutch.
“And he did old school to get in Starskin Hutch.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:28:12 · Chris Ryan (0.40 sure it was them)
unmapped (borrowed from): Old School → Life of the Party. Melissa McCarthy's Life of the Party is basically a solo Old School, down to the closing pop-star performance.
“That is basically like a solo old school about how she goes back to school.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:28:32 · Sean Fennessey (0.40 sure it was them)
people (stunt casting): Craig Kilborn → Old School. Kilborn was stunt-cast and could not act, delivering lines like Daily Show jokes.
“he's reading his lines like he would read daily show jokes.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:29:54 · Sean Fennessey (0.40 sure it was them)
people (same director craft): Old School → The Hangover. Phillips later masters the story-inside-the-credits trick with the Polaroids in The Hangover.
“Todd Phillips, like, masters this with the hangover closing credits.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:31:07 · Sean Fennessey (0.40 sure it was them)
craft (craft): Old School → Whitesnake. Whitesnake's Here I Go Again plays four times on the Old School soundtrack.
“And I mean, here I go again, I think, is played 4 times. That's a lot of white snake.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:31:48 · Chris Ryan or Sean Fennessey (0.35 sure it was them)
career (career peaks): Luke Wilson → The Royal Tenenbaums. Old School and Tenenbaums are the alpha and omega of Luke Wilson.
“This and Tennenbaums are the two, that's the alpha and the omega of Luke Wilson.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:32:10 · Chris Ryan (0.60 sure it was them)
craft (shared structural flaw): Old School → Back to School. The late competition-element plot is a flaw borrowed from Back to School and also seen in Stripes' war.
“when it starts to become too much like back to school, you know, where there's like a competition element to it.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:34:32 · Bill Simmons (0.50 sure it was them)
lineage (genre lineage): Animal House → Old School. Animal House started the habit of a winnable conflict set-piece that comedies copied for ten years, and Old School revived it.
“I think Animal House started it and then the next 10 years of comedy is ripped off”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:34:48 · Bill Simmons (0.50 sure it was them)
career (career regret): Brian Callen → Old School. Callen is the favorite guy from that era who never fully broke through; Bill blames his agent.
“Brian Callen is my favorite guy who didn't totally make it from that era.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:38:26 · Bill Simmons (0.40 sure it was them)
lineage (unmade sequel): Old School → Old School 2 (unmade sequel script). A 2006 sequel script about spring break was turned down by Ferrell and Vaughn as repetitive.
“It felt like it was repeating.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:42:01 · Bill Simmons (0.40 sure it was them)
lineage (sequel wish list): Wayne's World 2 → Old School. Asked which comedy sequel they'd want, Old School 2 beats Wedding Crashers 2; Wayne's World 2 is the great comedy sequel.
“I think is a genius movie.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:43:10 · Sean Fennessey (0.40 sure it was them)
theme (location reuse): Old School → Back to the Future. The house used as the frat house in Pasadena also appeared in Back to the Future, Back to the Future Part II, and Teen Wolf.
“It's been used for 3 Michael J. Fox movies.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:45:01 · Bill Simmons (0.50 sure it was them)
verdict (career apex): Vince Vaughn → Wedding Crashers. Chris argues Vaughn's apex is Wedding Crashers, a year after Old School, when he is clearly a star not a fluke.
“Now it's not a fluke.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:47:25 · Chris Ryan (0.50 sure it was them)
career (career run): Luke Wilson → Legally Blonde. Old School is part of Wilson's mainstream bankable run from Legally Blonde through Charlie's Angels.
“it's like legally blonde to Charlie's Angels, this.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:47:48 · Chris Ryan (0.55 sure it was them)
career (career debt): Luke Wilson → Wes Anderson. Bill argues Wilson owes his good roles to his brother Owen and Wes Anderson.
“I think he is the beneficiary of having a very creative brother, and forging a partnership with Owen and Wes Anderson”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:48:53 · Bill Simmons (0.50 sure it was them)
theme (repeated persona): Luke Wilson → Bottle Rocket. His doe-eyed innocent persona in Bottle Rocket recurs in Charlie's Angels, Legally Blonde, and Old School.
“He's very good in bottle rocket because he plays this kind of doe eye, innocent type”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:49:06 · Bill Simmons (0.45 sure it was them)
what-if (career what-if): Luke Wilson → Harrison Ford. Chris says Wilson had an action-lead path like Ford if he had stayed in game shape; the others mock it.
“I think if Luke Wilson had stayed in game shape. I think there's a there is like an action movie path for him.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:50:24 · Chris Ryan (0.85 sure it was them)
career (career comparison): Elisha Cuthbert → The Girl Next Door. Cuthbert's best film work, with a cast Chris wanted more from; Cuthbert's movie career stalled after rom-coms died.
“She pretty much never made another comedy after the girl next door.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:51:50 · Chris Ryan (0.45 sure it was them)
unmapped (screenwriter red flag): The Girl Next Door → Armageddon. Six credited screenwriters on The Girl Next Door is a red flag, as on Armageddon.
“So does Armageddon.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:52:38 · Chris Ryan (0.40 sure it was them)
people (character-actor trail): Patrick Fischler → Mulholland Drive. Fischler, the Piven henchman, is the guy telling the diner story in Mulholland Drive.
“What is he's also so memorable in Mulholland Drive, where he tells the story in the diner”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:54:10 · Sean Fennessey (0.40 sure it was them)
craft (shared device): Old School → Wedding Crashers. Both open with a wedding; Bill calls it his open-your-movie-with-a-wedding theory.
“This movie also nicely slots into my open your movie with a wedding theory.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:01:05 · Bill Simmons (0.60 sure it was them)
unmapped (shared line): Old School → The Godfather. Old School features the characters calling Luke Wilson 'Godfather'; the host also notes the Godfather timeline.
“Godfather. Godfather.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:04:59 · Bill Simmons (0.40 sure it was them)
craft (joke structure): Old School → Fight Club. The Godfather secret in front of Pompeo works like a Fight Club rule about not talking about it outside.
“It's a great, like, fight club joke.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:05:13 · Sean Fennessey (0.40 sure it was them)
unmapped (producing partnership): Todd Phillips → Bradley Cooper. Phillips and Bradley Cooper are producing partners, so Phillips could be on stage if A Star Is Born wins.
“he and Bradley Cooper are producing partners.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:06:24 · Sean Fennessey (0.60 sure it was them)
lineage (mentor-style lineage): Todd Phillips → Ivan Reitman. Phillips' skill of picking people at the right time is something Bill says he learned from Reitman.
“clearly he learned that from Ivan Reitman, who was amazing at that in the 70s, 80s, and 90s.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:07:28 · Bill Simmons (0.50 sure it was them)
unmapped (hometown): Todd Phillips → Sean Fennessey. Sean and Todd Phillips are both from Long Island's North Shore.
“the person who is also from the North Shore from my hometown is Todd Phillips, director of old school.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:09:33 · Sean Fennessey (0.85 sure it was them)
lineage (inspiration dispute): Frank Sinatra → The Godfather. Sinatra was mad because Johnny Fontane resembled him and the From Here to Eternity role; Sean denies Fontane is a Sinatra replica.
“Johnny Fontaine is not a replica of Frank Sinatra.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:12:49 · Sean Fennessey (0.50 sure it was them)

Fun items (24)

fun, about Todd Phillips: Phillips' first student documentary Hated, about punk singer GG Allin, got him an HBO internship; he helped develop Taxicab Confessions there, then made Frat House, later accused of staging scenes.
“It got him an internship at HBO.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:09:42 · Sean Fennessey (0.50 sure it was them)
fun, about The Hangover: The story is Phillips skipped an upfront check on the first Hangover and took points, earning $50 million on the original alone.
“he did not take a check for ahead of time for the hangover and that he took only points and that he made $50000000”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:10:44 · Sean Fennessey (0.40 sure it was them)
fun, about Roger Ebert: In the Roger Ebert category Bill reads his pan, then declares Ebert zero for two in 2019 and never to be trusted on comedies.
“never to be trusted on comedies.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:15:17 · Bill Simmons (0.50 sure it was them)
fun, about The Dan Band: Aged-the-best: the wedding band that swears its way through 'Total Eclipse of the Heart' and 'Every now and then I get a little bit terrified', with Ferrell and Reeves' faces worth freeze-framing. LA bar legends in the 2000s.
“If you freeze frame the look on Will Ferrell and Perry Reeves face.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:26:26 · Chris Ryan (0.30 sure it was them)
fun, about Snoop Dogg: A four-minute Snoop performance in the film is a good snapshot of Snoop time: Warren G as DJ and Don Magic Juan in tow, rumored trade-off for Starsky & Hutch.
“Warren G is his DJ and it's when he went everywhere with Don Magic Wand.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:28:03 · Sean Fennessey (0.30 sure it was them)
fun, about Craig Kilborn: Kilborn appears in both aged-the-best and aged-the-worst: a thrill to see him, but visibly terrified, reading lines like Daily Show jokes; he gets the Al Martino (worst actor) award.
“He's in 2 scenes, and then he crashes in the closing credits.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:29:50 · Bill Simmons (0.40 sure it was them)
fun, about Old School: The closing credits have a story: Kilborn crashes over a bridge and kills fly-fishing Jeremy Piven, then there are other bits, about 2.5 minutes. Phillips mastered the trick with The Hangover Polaroids, rated number-one closing credits by one host.
“I would say that's for me, that's the number one closing credits of all time.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:31:15 · Sean Fennessey (0.40 sure it was them)
fun, about Old School: Whole-soundtrack rundown: Papered Up, Dust in the Wind, Hungry Like the Wolf, Sound of Silence, Total Eclipse of the Heart, Metallica; Whitesnake's 'Here I Go Again' is played four times.
“I think, is played 4 times.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:31:48 · Bill Simmons (0.40 sure it was them)
fun, about Old School: Category winner for most iconic and aged-best bit: 'earmuffs'. The guys realized the word entered everyday speech from this movie and are sure they owe Vince Vaughn royalties; Bill says it's like Kleenex.
“Earmuffs. People still say it.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:32:44 · Chris Ryan (0.45 sure it was them)
fun, about Elisha Cuthbert: Aged-the-worst: Luke Wilson sleeping with a high school girl, who may be 17 or 18. Compared to the Stefania Simonetti situation in The Godfather.
“She's either 17 or 18.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:36:02 · Sean Fennessey (0.40 sure it was them)
fun, about Juliet Lewis: Dion Waiters Award winner (biggest heat check): she is only in two scenes, one the closing credits, and is basically an amateur porn star before amateur porn stars.
“She's basically like an amateur porn star before we even knew there were amateur porn stars.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:37:00 · Sean Fennessey (0.40 sure it was them)
fun, about Seann William Scott: Nominee for Dion Waiters Award: he plays Peppers, the animal trainer, yanking a goat's chain and telling it to shut up; 'You just took one in the jugular, man' after the dart-gun party.
“You just took one in the jugular, man.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:37:49 · Chris Ryan (0.30 sure it was them)
fun, about Old School 2 (unmade sequel script): A 2006 sequel script, 'Old School Dose', about an aging frat on spring break, was written by Scott Armstrong and refused by Ferrell and Vaughn as too repetitive; Luke Wilson said in 2016 he would do it.
“Luke Wilson was game saying, I, of course, would do it at the drop of a hat.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:43:38 · Bill Simmons (0.40 sure it was them)
fun, about Will Ferrell: Ferrell really ran naked in the streaking sequence, horrifying locals at a 24-hour gym; the second part filmed during the Snoop performance and he needed a drink first.
“In the streaking sequence, Will Ferrell ran naked for real.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:44:02 · Bill Simmons (0.45 sure it was them)
fun, about Patrick Cranshaw: Blue was played by Patrick Cranshaw, a 50-year working actor who was the sheriff in all the Air Bud movies and died about four years after the film.
“although I will say he played the sheriff in all the Airbud movies.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:44:34 · Bill Simmons (0.50 sure it was them)
fun, about Old School: Half-ass internet research: the frat house is a real Pasadena house on Bushnell Avenue, also used in Back to the Future, Back to the Future Part II, and Teen Wolf. Bill stumps the others with a quiz.
“It's been used for 3 Michael J. Fox movies.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:45:01 · Bill Simmons (0.50 sure it was them)
fun, about Luke Wilson: Chris Ryan's hot take that Luke Wilson was in the Harrison Ford zone and could have been an action star becomes a running bit; the others call it among the worst takes ever and joke about a Luke Wilson Fugitive.
“Alisha Cuthbert could have been Elaine May.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:51:19 · Bill Simmons (0.40 sure it was them)
fun, about Patrick Fischler: Joey Pants Award: the Mad Men guy, Piven's henchman, is Patrick Fischler; they mention Patrick Adams, star of Suits, playing guitar during Dust in the Wind as an alternate.
“That's how you win the Joey Pants Award, and I have no idea what your name is.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:54:31 · Bill Simmons (0.40 sure it was them)
fun, about Andy Dick: Joey Pants Award runner-up winner: Andy Dick is out of his mind in one scene.
“Andy Dick's out of his mind in this in that one scene, though.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:55:22 · Chris Ryan (0.30 sure it was them)
fun, about Old School: Bill's wedding-toast tangent: he wants a TV show or YouTube channel of brutal best-man speeches and tells of watching a wedding from a Torrey Pines hotel balcony with a bottle of wine.
“I always thought this should be a TV show.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:59:27 · Bill Simmons (0.50 sure it was them)
fun, about Old School: Best quote contest: 'Blue, you're my boy!', Frank's earmuffs and 'cockballs' bit, and Mitch's 'Columbus wasn't looking for America' line.
“well, Columbus wasn't looking for America, my man, but that turned out pretty okay for everyone.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:02:01 · Sean Fennessey (0.40 sure it was them)
fun, about Old School: Unanswerable question: who is the 2019 Craig Kilborn? Suggestions include Logan Paul, Joe Buck, Gus Johnson, Jim Nantz, Jeff Van Gundy, Trevor Noah, and Jalen Rose.
“I was thinking it's Joe Buck.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:02:51 · Bill Simmons (0.40 sure it was them)
fun, about Todd Phillips: Who Won the Movie: Todd Phillips, who is arguably bigger than Apatow, is directing Joker, and might be on stage for A Star Is Born; he picks people at the right time.
“he definitely picks people at the right time.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:07:17 · Sean Fennessey (0.40 sure it was them)
fun, about The Godfather: Closing Godfather corrections: Corleone compound is in Long Beach, Sean is a proud North Shore guy, a reader notes Bobby Thompson's home run game on the radio, and a bit about the kids Kay was teaching.
“fuck the southern shore.”
The Rewatchables · ‘Old School’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 1:09:27 · Sean Fennessey (0.70 sure it was them)

Who's talking

Bill Simmons (host): Loves sports-adjacent silliness, big broad comedy and quotable lines, and wedding toast chaos. Can't stand being wrong about movie trivia he has already litigated. A sucker for his own running categories and bits (Ebert, Joey Pants, Dion Waiters).
Chris Ryan (host): Loves character-driven comedy stars, SNL, and a good unreasonable comp. Dislikes lazy TV-remake comedies like Starsky & Hutch. A sucker for Luke Wilson and for true-detective-style hype for his own show.
Sean Fennessey (host): Cinephile with filmmaker-career knowledge (Todd Phillips' documentaries, Phillips-Cooper partnership). Loves Wayne's World 2 and rewards deep-cut details. Not a fan of The Hangover sequels or the Godfather compound mistake.

The show's recurring bits

Apex Mountain: The moment a star peaks; where on the mountain a performance sits.
Who Won the Movie: The hosts name the person who came out of the film best off.
The Ebert review: Roger Ebert's original review and star rating read aloud. Ebert is cited, never on the show.
Casting what-ifs: Who was almost cast, or who should have been.
Most rewatchable scene: The scene each host would stop on while flipping channels.
Aged best / aged worst: What holds up and what does not.
Picking Nits: The little things in a film the hosts love that they don't think totally work: the nits.
Double feature: The film each host would pair it with; a programming pick.

Names the transcriber got wrong

'Sean Fantasy' = Sean Fennessey
'Cordleone' = Corleone
'Statboy' = Stat Boy (Bill's PTI reference)
'Night of the Roxbury' / 'Not at the Roxbury' = A Night at the Roxbury
'Jet Appetown' / 'Jet Appetite' = Judd Apatow
'Austin Harris' = Austin Powers
'Fairly brothers' = Farrelly brothers
'Sheila Evans' = Sheila Nevins
'Kilbert' / 'Coburn' / 'Carbo' = Craig Kilborn
'Perry Reeves' = Perrey Reeves
'Sean Williams Scott' = Seann William Scott
'Brian Cowen' / 'Brian Callen' = Brian Callen
'Dion Wader's Award' = Dion Waiters Award
'Joey Pantsward' = Joey Pants Award
'Saul Robinck' = Saul Rubinek
'Treyo Bushemi' = Steve Buscemi
'Elisha Cuthbert' appears as 'Alisha Cuthbert'
'Dark gun birthday party' = dart gun birthday party
'Ari Lang' = Artie Lange
'Metropalooza' = Metropolooza
'Chris Chilios' = Chris Chelios
'Ithaca University' is Road Trip's setting