Say Anything

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Overall episode#144Source sheet order

Movie year19891980s

Tomatometer98%Critics’ score

Metacritic86View score

Roger Ebert4/4Original star rating

DirectorCameron CroweRomance / Comedy

FROM THE CONVERSATION

What they said about the movie

The episode treats Say Anything as a defining late-80s high school movie: funny, warm, deeply observed, and unusually adult about first love, parents, and social awkwardness. The hosts and Judd Apatow emphasize Cameron Crowe’s specificity, the cast’s perfect chemistry, and the movie’s lasting emotional power, while noting a few dated elements like the boombox context and some IRS/nursing-home-fraud material.

Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

In this conversation

Bill Simmons

Chris RyanJudd Apatow

WHY IT WORKS

What made it rewatchable

01The opening clearly establishes Lloyd, Diane, and the central romantic pursuit while feeling like real teenage banter. About 32 min
02The party sequence is singled out as a near-perfect, highly detailed depiction of an actual high school party. About 32 min
03The boombox scene remains iconic because it is inseparable from the Peter Gabriel song and the movie’s romantic image-making. About 56 min
04The breakup and father-daughter confrontation scenes are praised for their emotional accuracy and writing. About 40 min
05The movie’s dialogue and character details have generated lasting quotes and bits that the hosts still enjoy repeating. About 1:12

WHAT DID NOT WORK

Their main criticisms

minorThe IRS/nursing-home-fraud subplot could be trimmed a little. About 16 min
minorThe boombox scene is less immediately impactful for younger viewers and needs more context now. About 56 min · medium confidence
minorDiane’s breakup with Lloyd feels slightly abrupt on first viewing, even if motivated by the father’s pressure. About 1:12
minorThe music choices feel like a near-miss for the exact late-80s/early-90s window they wanted. About 1:04 · medium confidence

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Opening cold open and Lloyd’s call plan

The opening with Lloyd’s friends sets up the movie’s tone, stakes, and humor immediately.

About 32 min

Favorite

Diane returns Lloyd’s call in the bathroom

A tense, funny landline scene that captures adolescent anxiety and romantic scrambling.

About 32 min

Favorite

The graduation/party sequence

The film’s centerpiece party is praised for its rooms, rhythms, chaos, and realism.

About 32 min

Favorite

Corey/Joe song scene

The weird, specific song-to-Joe reveal is treated as one of the funniest and most human details in the movie.

About 32 min

Favorite

Lloyd tells his friends he had sex

His friends’ reaction and Lily Taylor’s advice are discussed as a classic teen-comedy exchange.

About 40 min

positive

Dinner with Diane’s family

Lloyd’s anti-career speech and kickboxing declaration are a comedic highlight.

About 40 min

Favorite

Breakup scene

Diane dumping Lloyd right after he says 'I love you' is described as brutally accurate.

About 1:12

Favorite

Father-daughter final confrontation

The final scene between Diane and her dad is praised for emotional depth and a strong ending.

About 1:12

Favorite

Boombox outside Diane’s window

The iconic ending image with Peter Gabriel is still admired even if its cultural meaning has shifted.

About 56 min

WHERE THEY DISAGREED

The biggest debates

They partly agreed About 8 min

Cameron Crowe movie vs. John Cusack movie

Chris Ryan
It is primarily a Cameron Crowe movie because the characters and writing define it.

Bill Simmons
Cusack is central too, but Crowe’s authorship and the script make it feel like Crowe's film.

Judd Apatow
Crowe’s specificity and direction are the main reason it works.

They partly agreed About 32 min

Best rewatchable scene

Bill Simmons
The party sequence is the best and can be broken into multiple sub-scenes.

Chris Ryan
The party is also the best scene, especially through the drive-home ending.

Judd Apatow
The car-sex scene and father-daughter material are his favorite nonstandard choices.

They partly agreed About 56 min

How dated is the boombox scene?

Bill Simmons
It is iconic but younger viewers may not fully get it now.

Chris Ryan
The scene still works because the song and image remain powerful.

They left it as a friendly argument About 48 min

Should the nursing-home fraud subplot be shorter?

Bill Simmons
A little less of it would be fine.

Judd Apatow
He actually wants more of it and more backstory.

They left it as a friendly argument About 1:12 · medium confidence

Could the movie work as a 10-episode Netflix series?

Bill Simmons
Initially rejects the idea, then briefly imagines it could work.

Chris Ryan
Suggests a character-flip or side-character version might be interesting.

Judd Apatow
Does not push the idea, but treats it as a thought experiment.

19 People discussedActors, directors, writers, and producers

very favorableCameron CroweBill Simmons: Praised as the key creative force and a writer-director whose specificity and warmth shaped the movie. About 8 min very favorableJames L. BrooksJudd Apatow: Described as the movie’s producer and a crucial mentor figure who helped shape it without overpowering Crowe. About 8 min

neutralPolly PlattJudd Apatow: Mentioned as one of the film’s producers alongside James L. Brooks. About 8 min · medium confidence

very favorableJohn CusackChris Ryan: Seen as the ideal Lloyd Dobler and one of the movie’s main reasons it works. About 8 min

favorableIone SkyeBill Simmons: Praised as the perfect Diane Court and a key part of the film’s appeal. About 16 min

very favorableJohn MahoneyJudd Apatow: Admired for bringing real darkness, pride, and heartbreak to Diane’s father. About 1:12 favorableLily TaylorBill Simmons: Her friend character is praised for the breakup advice and comic authority. About 40 min favorableJeremy PivenBill Simmons: Cited as an over-the-top scene-stealer in the party sequence. About 1:12 favorableEric StoltzBill Simmons: Noted as a memorable small-role presence and a heat-check candidate. About 1:12

favorablePeter GabrielBill Simmons: His song is treated as inseparable from the boombox scene and one of the movie’s most iconic elements. About 56 min

favorablePhil Baker HallJudd Apatow: Mentioned for the nursing-home fraud scene and its comic detail. About 48 min

favorablePamela AdlonBill Simmons: Praised for being part of the opening friend group and for later Ringer-adjacent familiarity. About 32 min

mixedJoseph Anderson ('Joe')Judd Apatow: Discussed as Diane’s boyfriend and an emblem of how painfully wrong teenage crushes can be. About 40 min

neutralDick Van DykeBill Simmons: Mentioned as a casting what-if for Diane’s father. About 1:04 · medium confidence

neutralRichard DreyfussBill Simmons: Cited as another casting what-if, wanting to play the Lloyd role. About 1:04 · medium confidence neutralChristian SlaterChris Ryan: Discussed as a rejected Lloyd alternative who felt too close to his other teen roles. About 32 min neutralRobert Downey Jr.Bill Simmons: Mentioned as having turned down the Lloyd role. About 32 min neutralAmy HeckerlingBill Simmons: Referenced in a digression about music choices in Fast Times at Ridgemont High. About 1:04 · medium confidence favorableMike NicholsBill Simmons: Quoted on the value of comedies being rewatched rather than rewarded. About 24 min

15 Conversation takesSpeakers shown only where the transcript identifies them

Judd ApatowLoved it

Says the movie reflected his friend group and helped make him want to make movies.

About 8 min

Chris RyanLoved it

Say Anything

Treats it as a nearly perfect high school movie with unforgettable characters.

About 8 min

Bill SimmonsLoved it

The party sequence

Argues the party scene is the movie’s best stretch and maybe the foundational high-school-party scene.

About 32 min

Judd ApatowLiked it

Producer notes/mentorship

Explains that his job as a producer is to nudge filmmakers toward unresolved questions without derailing them.

About 8 min

Chris RyanLoved it

Lloyd Dobler

Likes Lloyd as a quirky, mid-pack guy who uses humor and charm instead of status.

About 16 min

Bill SimmonsLiked it

The boombox scene

Calls the boombox scene iconic but notes its cultural context is harder for younger viewers now.

About 56 min

Chris RyanLoved it

The breakup scene

Says Diane’s breakup is devastating and perfectly captures teenage rejection.

About 1:12

Judd ApatowLoved it

John Mahoney

Sees Mahoney as the movie’s emotional dark center and praises his final rage and sadness.

About 1:12

Bill SimmonsLiked it

Jeremy Piven

Finds Piven’s party-scene energy hilarious and intentionally overdone.

About 1:12

Bill SimmonsMixed

Teen friendships as toxic

Argues the movie shows how friends can give terrible advice and should sometimes be outgrown.

About 40 min

Chris RyanLiked it

High Fidelity TV adaptation

Uses the later TV adaptation as evidence that this kind of story can work in another format.

About 1:04 · medium confidence

Bill SimmonsLoved it

John Cusack

Thinks Cusack had major star power here and later had multiple peaks across his career.

About 32 min

Judd ApatowLoved it

Say Anything ending

Thinks the ending is one of the best romantic-movie endings, alongside The Graduate and Before Sunset.

About 48 min

Bill SimmonsLoved it

Lloyd’s career speech to Diane’s father

Loves the absurd sincerity of Lloyd’s anti-career/kickboxing monologue.

About 40 min

Chris RyanLoved it

The party

Says the party scene is his favorite because it captures the best night of someone’s life.

About 1:12

6 ThemesThe larger ideas in the discussion

First love as a turning point

The movie is treated as a defining portrait of teenage romance, with Lloyd and Diane feeling universally recognizable rather than generic.

About 8 min

Parents and children

The father-daughter material is described as heartbreaking, especially once viewed from an adult or parent perspective.

About 16 min

Cameron Crowe’s specificity

They admire Crowe’s ability to make characters, parties, and dialogue feel lived-in and exact.

About 24 min

The power of supporting characters

Nearly every side character is treated as fully drawn and potentially worthy of their own movie.

About 40 min

Comedy versus awards recognition

The conversation broadens into a defense of comedy films that are loved and rewatched even when awards bodies miss them.

About 24 min

The late-80s high school movie as a transitional genre

They frame Say Anything as a bridge from John Hughes-style teen movies into a more modern, emotionally sophisticated era.

About 16 min

23 Facts and referencesProduction notes and other movies mentioned

Production note

Cameron Crowe originally did not direct Fast Times at Ridgemont High; he wrote the book based on high-school reporting.

About 16 min

Production note

James L. Brooks reportedly came up with the germ of the story by imagining a father-daughter crossing scene with a criminal father.

About 16 min · medium confidence

Production note

John Cusack still kickboxes, according to the episode’s discussion of Lloyd and the sport.

About 1:04

Production note

The boombox model was identified as a Toshiba RT-SX1.

About 1:04

Production note

Peter Gabriel’s song rights may have been cleared under a mistaken assumption about another film titled Wired.

About 56 min · medium confidence

Production note

Cameron Crowe rejected The Smithereens’ 'A Girl Like You' because it revealed the plot too much.

About 1:04

Production note

Bill says he borrowed material from Say Anything for The 40-Year-Old Virgin.

About 32 min

Production note

The episode notes that John Cusack’s casting helped define a long teen-to-adult run from 16 Candles through Say Anything and beyond.

About 32 min

Fast Times at Ridgemont High

Used as a key Cameron Crowe antecedent and formative influence.

About 8 min

The Sure Thing

Cited as an earlier John Cusack movie that built his persona.

About 8 min

Broadcast News

Mentioned as another James L. Brooks production-era benchmark.

About 8 min

The Big Sick

Used as an example of Judd Apatow’s producing/notes process.

About 8 min

The 40-Year-Old Virgin

Referenced multiple times as a film Judd worked on and stole from Say Anything.

About 8 min

Tommy Boy

Used in a discussion of comedies critics and awards voters miss.

About 24 min

The Cable Guy

Cited as another comedy critics split on, with one host noting Siskel’s support.

About 24 min

Superbad

Referenced for a risky scene and a memorable test screening with Cameron Crowe present.

About 48 min

Almost Famous

Mentioned as another Crowe film with similar youth/character sensitivity and a party scene lineage.

About 24 min

The Graduate

Used as a benchmark for great romantic endings.

About 48 min

Before Sunset

Referenced as another elite romantic ending.

About 48 min

High Fidelity

Discussed as a later Cusack-related or adaptation-related comparison point.

About 1:04

Singles

Mentioned as a more obvious Seattle movie and as another Custack-adjacent 90s movie.

About 1:28

Freaks and Geeks

Used by Judd as an example of capturing realistic party behavior and teen life.

About 40 min

Ricky Don't Lose That Number

Referenced as a song Bill associates with the father character’s proud mood.

About 1:20 · medium confidence

10 Running jokes and short linesRecurring bits captured from the conversation

Bill’s shameless theft from the movie

Bill repeatedly jokes about borrowing Say Anything ideas for his own work.

About 32 min

Kickboxing as the sport of the future

Lloyd’s kickboxing line becomes a recurring joke, including speculation that he was ahead of his time.

About 40 min

Piven heat / overacting award

Jeremy Piven’s party performance is treated as a comedic awards-category lock.

About 1:12

The 'Joey Pants' / that guy discussion

The show riffs on best-that-guy casting and the unforgettable minor-role energy in the film.

About 1:20 · medium confidence

Rewatchables as the real awards

The hosts joke that the podcast’s judgment matters more than the Oscars for some comedies.

About 24 min

Bill Simmons

“I gave her my heart, and she gave me a pen.”

Opening minutes

Bill Simmons

“I'm an athlete, so I rarely drink.”

Opening minutes

Bill Simmons

“I don't want to sell anything, buy anything”

About 40 min

Bill Simmons

“You must chill!”

About 1:12

Judd Apatow

“I can't really tell if I'm great”

About 48 min

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

Checking where Say Anything is available…

WHAT TO WATCH NEXT

Movies to watch before and after.

Three movies to watch before Say Anything, and three to watch next.

Finding six movies…Three to watch first and three to watch next.

ON THE MIC

3 voices on this episode

Bill SimmonsThe Rewatchables

Chris RyanThe Rewatchables

Judd ApatowThe Rewatchables

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