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THE REWATCHABLES · June 27, 2024

Big Daddy

A 1999 comedy / drama directed by Dennis Dugan, covered in the complete Rewatchables archive.

ComedyDrama1990sDirected by Dennis Dugan
Overall episode#71Source sheet order
Movie year19991990s
Tomatometer39%Critics’ score
Metacritic42View score
Roger Ebert—No review recorded
DirectorDennis DuganComedy / Drama

FROM THE CONVERSATION

What they said about the movie

The episode argues that Big Daddy is a transitional Adam Sandler movie: still built on his man-child persona, but more polished, relationship-driven, and commercially successful than his earlier work. The hosts are mixed on the movie itself but appreciative of its place in Sandler’s run, its rewatchability, and the way it helped define late-1990s comedy.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

WHY IT WORKS

What made it rewatchable

  1. 01Sandler’s chemistry with Leslie Mann/JLA-type romantic dialogue is repeatedly cited as a key appeal. About 8 min
  2. 02The surprise birthday party sequence and the early social awkwardness are described as especially memorable. About 24 min
  3. 03The McDonald’s breakfast outburst and other broad physical/comic set pieces are seen as big-laugh scenes. About 32 min
  4. 04The kangaroo hockey scene is singled out as a favorite repeat-watch moment. About 32 min
  5. 05The movie’s soundtrack and 1999 pop-culture texture make it easy to revisit as a time capsule. About 40 min · medium confidence

WHAT DID NOT WORK

Their main criticisms

  1. majorThe core premise is implausible and emotionally unconvincing, especially the adoption storyline and the child-custody stakes. About 40 min
  2. majorThe Hooters jokes and Leslie Mann material feel dated and make the movie age badly. About 32 min
  3. moderateSandler’s emotional reaction after social services takes the child away is described as bad acting. About 48 min
  4. moderateSome of the gags are too broad or antisocial to play cleanly now. About 32 min
  5. moderateThe movie is seen as overlong and with a boring trial section. About 40 min · medium confidence

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Surprise birthday party for Jon Stewart’s character

The opening party disaster is singled out as the most rewatchable and representative scene.

About 24 min
positive

McDonald’s breakfast blowup

Sandler’s loud confrontation at breakfast is remembered as a big comic set piece.

About 32 min
mixed

Rollerblader park prank

The stick prank against the rollerbladers is funny but also aggressively antisocial.

About 32 min
Favorite

Kangaroo hockey argument

Sandler’s choice of a kangaroo TV special over a hockey playoff moment is highlighted as a great bit.

About 32 min
critical

Trick-or-treating / home-invasion gag

The scene where he keeps entering a stranger’s house is treated as a strange and bad idea.

About 48 min
critical

Trial / social services hearing

The courtroom sequence is considered the movie’s least effective stretch.

About 40 min
critical

Child watch-TV sequences

Bill objects that the kid is watching shows too advanced for a five-year-old.

About 48 min · medium confidence
critical

Sandler’s emotional breakdown after losing custody

His reaction after the child is taken away is judged as weak acting.

About 48 min

WHERE THEY DISAGREED

The biggest debates

They partly agreed About 8 min

Is Big Daddy actually a good Sandler movie or just commercially successful?

Bill Simmons

He likes it but sees it as a strange, imperfect transitional movie.

Sean Fennessey

He is more negative and calls it his least favorite of the early run.

Joe House

He accepts its success and argues it makes sense commercially.

They left it as a friendly argument About 16 min

Punch-Drunk Love’s quality

Sean Fennessey

It is an all-time classic.

Bill Simmons

It is fine but not at that level.

Joe House

It is a weird-rom-com classic for weirdos.

They agreed About 32 min

The film’s treatment of the gay-friends subplot

Bill Simmons

It is surprisingly progressive for 1999 and mostly holds up.

Joe House

It is one of the few things that aged the best.

They agreed About 8 min

Whether the movie should be watched with kids

Bill Simmons

No, because the Hooters and adult material make it a bad fit.

Joe House

He tried it with his son and regretted it.

19 People discussedActors, directors, writers, and producers
mixedAdam SandlerBill Simmons: Praised as the biggest comedy movie star of the era and for his career breadth, but criticized for some bad acting and dated material. About 8 min favorableLeslie MannBill Simmons: Viewed as an especially strong comic presence and part of one of the movie’s best elements. About 40 min
neutralJon StewartBill Simmons: Discussed as a supporting-player-turned-late-night star who appears in the film before his big TV era. About 24 min
favorableDrew BarrymoreBill Simmons: Held up as a great romantic partner for Sandler in The Wedding Singer and part of his best on-screen chemistry. About 16 min favorableJennifer AnistonJoe House: Cited as one of the actresses Sandler could plausibly be paired with in his romantic-comedy era. About 40 min favorableJulie BowenBill Simmons: Mentioned as another strong Sandler leading lady from earlier in his career. About 40 min mixedChristy SwansonBill Simmons: Presented as a 1990s screen presence the hosts liked, though they debate whether she reached her ceiling. About 40 min favorableSteve BuscemiBill Simmons: Noted as a fun Sandler collaborator in a cameo-like role. About 32 min favorableSean FennesseyBill Simmons: Used as an interlocutor for the Sandler canon discussion; he is especially positive about Punch-Drunk Love and other films. About 8 min neutralBill MurrayBill Simmons: Mentioned as a possible casting option for the lead role. About 48 min · medium confidenceneutralJack NicholsonBill Simmons: Mentioned as another possible lead casting option and later as a point of comparison for Anger Management. About 48 min · medium confidence
neutralDylan and Cole SprouseBill Simmons: Cited as the child actor twins in the movie and as later Disney-channel stars. About 48 min
favorableAlan CovertBill Simmons: Referenced as a frequent Sandler collaborator and one of the gay friends in the film. About 48 min
criticalRob SchneiderBill Simmons: Described as overly Rob Schneider-y, with a goofy and borderline racist character design. About 48 min
favorableJoseph BolognaBill Simmons: Noted as a reliable older-character type in the movie. About 48 min
favorableJudd ApatowBill Simmons: Praised indirectly through Leslie Mann’s career and the broader Apatow ecosystem. About 40 min · medium confidenceneutralRoger EbertBill Simmons: His negative review is cited as emblematic of critical backlash. About 24 min
neutralDave MatthewsJoe House: Mentioned as one of the surprising cast/guest-name examples in another Sandler film. About 40 min · medium confidence
neutralDan PatrickJoe House: Mentioned as a cameo/key-role example in a later Sandler movie. About 40 min · medium confidence
15 Conversation takesSpeakers shown only where the transcript identifies them
Bill SimmonsLiked it

Big Daddy as a transitional Sandler movie

Bill argues the film is more mature than Sandler’s earlier comedies and marks a pivot in his career.

About 8 min
Joe HouseDid not like it

The Waterboy

House sees The Waterboy as too one-note and too far over the top.

About 24 min
Sean FennesseyLiked it

Punch-Drunk Love

Sean defends Punch-Drunk Love as an all-time classic and pushes back against the others.

About 16 min
Bill SimmonsLiked it

The surprise birthday party

Bill says this opening sequence is his favorite scene because it captures party-era dysfunction.

About 24 min
Joe HouseLiked it

Just Go With It

House makes a strong case that this later Sandler rom-com is very rewatchable and fun.

About 40 min
Bill SimmonsLiked it

Grown Ups

Bill defends the Grown Ups films as straightforward hangout movies that do exactly what Sandler intended.

About 16 min
Bill SimmonsLoved it

Adam Sandler

Bill repeatedly frames Sandler as a huge, durable star whose movie career and multi-phase appeal are remarkable.

About 8 min
Joe HouseLiked it

Sonny Koufax

House likes the name as a slacker identity and thinks it fits the character type well.

About 24 min
Bill SimmonsLiked it

Leslie Mann

Bill repeatedly praises Mann and singles her out as the movie’s best cast-related element.

About 40 min
Bill SimmonsLiked it

McDonald’s breakfast meltdown

Bill enjoys the scene despite its aggression because it is so over-the-top.

About 32 min
Bill SimmonsLiked it

The Wedding Singer

Bill and the others view it as Sandler’s attempt to prove he could do a sweeter, more adult rom-com.

About 16 min
Joe HouseLoved it

Happy Gilmore

House identifies it as his favorite Sandler film and one of the most rewatchable comedies ever.

About 16 min
Bill SimmonsMixed

Big Daddy

Bill likes the movie but says it has aged strangely and is among the harder Rewatchables 1999 titles to categorize.

Opening minutes
Sean FennesseyDid not like it

Big Daddy

Sean is the harshest on the film’s quality, calling it his least favorite among the early Sandler hits.

About 8 min
Bill SimmonsLiked it

The kangaroo hockey-TV argument

Bill finds the argument and the kangaroo bit especially rewatchable.

About 32 min
5 ThemesThe larger ideas in the discussion

Adam Sandler’s career arc

The episode frames Big Daddy as a pivot point between juvenile SNL-derived comedy and more adult, relationship-based work.

About 8 min

Late-1990s comedy culture

The discussion uses the film to revisit an era of cable rewatching, DVDs, and broader bro-comedy standards.

About 16 min

Nostalgia for pre-texting social life

The movie’s party/disappearing/looking-for-people chaos resonates as a marker of pre-phone socializing.

About 24 min

Progress and discomfort around sexuality/gender

The hosts note the movie’s casual misogyny while also acknowledging a surprisingly progressive gay-friends subplot for the time.

About 32 min

Sandler’s casting instincts

They admire how often Sandler cast convincing romantic leads and strong comic ensembles.

About 16 min
24 Facts and referencesProduction notes and other movies mentioned

Production note

Big Daddy was described as the most successful Sandler film of the 1990s.

About 24 min

Production note

The film opened to about $41.5 million in 1999 and grossed about $163 million.

About 24 min

Production note

Bill says Roger Ebert gave the film 1.5 stars and called it a child-welfare-case movie.

About 24 min

Production note

Adam Sandler’s wife Jackie appears in a cameo as a waitress.

About 48 min

Production note

The young boy was played by the Sprouse twins.

About 48 min

Production note

The urination scenes were faked with hand pumps.

About 48 min

Production note

The episode notes this was Sandler’s last comedy before founding Happy Madison Productions.

About 48 min

Production note

Sandler’s early SNL material and songs are treated as a major part of his appeal.

About 8 min

Production note

The movie is linked to Syracuse through repeated references.

About 48 min · medium confidence

SNL monologue / Saturday Night Live hosting

Used to discuss Sandler’s comeback and long career arc.

Opening minutes

Happy Gilmore

Compared as part of Sandler’s early run and cited as highly rewatchable.

About 16 min

Billy Madison

Used as another early Sandler example of similar comedic structure.

About 8 min

The Wedding Singer

Discussed as Sandler’s sweeter romantic pivot.

About 16 min

The Waterboy

Used as the next movie after his early successful run and as a one-note comparison point.

About 24 min

Little Nicky

Cited as a major post-Big-Daddy misfire in Sandler’s career.

About 24 min

Punch-Drunk Love

Debated as Sandler’s serious-actor milestone.

About 16 min

Mr. Deeds

Mentioned as a mid-2000s Sandler comedy that is fine but not essential.

About 24 min

50 First Dates

Cited as the start of his adult rom-com phase.

About 24 min

Funny People

Held up as Sandler’s most interesting later movie and a strong performance vehicle.

About 24 min

Meyerowitz Stories

Used as another example of Sandler’s strong dramatic acting.

About 24 min

Just Go With It

Discussed as a later Sandler rom-com with an impressive cast and Hawaiian setting.

About 40 min

Grown Ups

Used to illustrate Sandler’s hangout-movie business model with friends.

About 16 min

The New Radicals / “You Get What You Give”

Referenced as part of the soundtrack’s late-1990s feel.

About 40 min · medium confidence

The Daily Show

Referenced indirectly through Jon Stewart’s later career trajectory.

About 24 min
11 Running jokes and short linesRecurring bits captured from the conversation

Sandler canon / early five-year run

The hosts repeatedly enumerate and compare Sandler’s 1995-99 movies, treating them as a distinct comedy era.

Opening minutes

Childhood vs adult viewing standards

They joke about whether the movie is appropriate for kids and how their own sons would react.

About 8 min

Party-era disappearing acts

The hosts riff on the pre-texting era of losing track of people at parties and hoping to find them later.

About 24 min

Hooters shame commentary

They repeatedly return to the movie’s Hooters references as the clearest sign of what has aged badly.

About 32 min

Sandler impressions

Bill attempts and immediately rejects his own Sandler voice impression while quoting lines.

About 32 min

Spade-assance

They joke about David Spade having a career resurgence and coin a playful term for it.

About 40 min

Bill Simmons

“Big Daddy should be reported”
About 24 min

Joe House

“the goddamn Jets, and I wipe my own ass”
About 8 min

Bill Simmons

“It's only Sonny. It's only Sonny.”
About 24 min

Bill Simmons

“HORSESHIT! HORSESHIT!”
About 32 min

Joe House

“I'm going to make the case for Just Go With It”
About 40 min

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

Checking where Big Daddy is available…

WHAT TO WATCH NEXT

Movies to watch before and after.

Three movies to watch before Big Daddy, and three to watch next.

Finding six movies…Three to watch first and three to watch next.
Includes a Rewatchables episodePosters from TMDB.

ON THE MIC

3 voices on this episode

Bill Simmons headshotBill SimmonsThe Rewatchables
Sean Fennessey headshotSean FennesseyThe Rewatchables
Joe HouseThe Rewatchables

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