'Happy Gilmore 2,' 'The Naked Gun,' and the 21st-Century Comedy Movie Crisis

The news rundownsequels, remakes, and a lot of Aaron Sorkin casting

My Best Friend's Wedding 1997

Celine Song is reportedly writing a sequel. Amanda calls the original a sacred text and maybe her favorite Julia Roberts film; she is bracing to hate it and hoping she won't.

Past Lives 2023

Cited as evidence Song can filter a love triangle into a plain structure and get something deep out of it.

Materialists 2025

Song's second feature. Sean thinks it less successful than 'Past Lives' but more interesting to argue about; Craig admits he still hasn't seen it.

Ticket to Paradise 2022

Raised as the model to avoid, the older stars ushering in a younger generation. Amanda would rather the sequel just show what happens after the wedding.

The Godfather Part II 1974

The 'what if the sequel is actually great' benchmark the table keeps joking about.

The Devil Wears Prada 2 2026

Grouped with the 'My Best Friend's Wedding' news as another beloved title from Amanda's world getting reopened.

The Social Network 2010

Aaron Sorkin is reportedly writing and directing a sequel with Mikey Madison and Jeremy Allen White eyed for roles. David Fincher and Jesse Eisenberg are not attached; the table thinks Sorkin needs a directing counterweight.

Now You See Me: Now You Don't 2025

Brought up to argue Eisenberg isn't above returning to a franchise: he loves close-up magic.

Is This Thing On 2025

Bradley Cooper's new film, with Will Arnett, about a stand-up comedian. Announced as the New York Film Festival closing-night film, which makes Amanda nervous about its awards odds.

Blitz 2024

Steve McQueen's film, a recent NYFF closing-night pick that fizzled, part of why Amanda distrusts the slot.

Ferrari 2023

Michael Mann's film, the other hyped NYFF closer that faded from the conversation.

The Irishman 2019

The exception: a profoundly New York movie that launched from the festival and stuck.

Rental Family 2025

The other Searchlight contender, premiering at TIFF; Searchlight hasn't missed a Best Picture nomination since 2017.

A Star Is Born 2018

Cooper's directorial debut, cited alongside 'Maestro' as his push to be taken seriously.

Maestro 2023

Sean logs himself as pro-'Maestro,' a fun theatrical experience, while wondering if 'Is This Thing On' is pitched at a quieter register.

The Trial of the Chicago 7 2020

Jeremy Strong played Jerry Rubin for Sorkin here; Strong is now the reported pick to play Zuckerberg in the sequel.

Being the Ricardos 2021

Grouped with 'Chicago 7' as Sorkin-directed films that got acting nominations but the table finds flawed.

Molly's Game 2017

Sean's pick for the strongest of Sorkin's directorial efforts.

Steve Jobs 2015

Held up as proof Sorkin does his best work with a strong collaborator, here Danny Boyle.

Springsteen: Deliver Me From Nowhere 2025

Mentioned because Jeremy Strong and Jeremy Allen White share it, so the 'Social Network' casting rumor comes with a working relationship attached.

'Happy Gilmore 2'a legacy sequel, 28 years and 30-plus minutes later

Happy Gilmore 2 2025

Directed by Kyle Newacheck, co-written by Adam Sandler and Tim Herlihy. Craig calls it maybe the worst movie he's ever seen, a YouTube compilation of cameos; Amanda thumbs it down as a comedy but confesses the golf-world fan service worked on her. Sean argues it's bad and weirdly honest, a meditation on death and alcoholism with Sandler's own family folded in. The most-viewed Netflix film in its opening weekend.

Happy Gilmore 1996

The 89-minute original, the most quoted comedy on the table and a foundational text for all three. Its outsider-breaks-into-golf structure is what the sequel can't reuse, so it strands Happy at the bottom again.

Billy Madison 1995

Sean's favorite Sandler movie, the feature that rewired his sense of what comedies could be, set against 'Happy Gilmore' as the actual breakout hit.

Murder Mystery 2019

Cited as one of the most-watched films in Netflix history and proof Newacheck-adjacent Sandler product travels.

Murder Mystery 2 2023

The sequel Sean half-remembers watching, or maybe just the trailer, while making the point about Sandler's Netflix machine.

Game Over, Man! 2018

Newacheck's Workaholics-crew movie, offered as evidence he's a proven Netflix commodity.

Caddyshack 1980

The reference point for the golf-outsider comedy, and the reminder that these movies were never sophisticated.

Tin Cup 1996

The other golf comedy about a rebel infiltrating a staid world.

Jurassic World Rebirth 2025

Sean's counter-case: he'll happily call this cynical garbage, yet 'Happy Gilmore 2' doesn't make him angry the same way.

Hustle 2022

Held up as the Sandler that shows why Sean stays generous: the actor still chases interesting filmmakers between the paydays.

You Are So Not Invited to My Bat Mitzvah 2023

The film that starred Sandler's daughter, part of the family-business pattern the table finds notable, if not exactly a case for quality.

The summer check-ina quick scorecard before the second review

F1 2025

The classic summer tentpole: very fast, biggest screen possible, a throwback Brad Pitt star turn.

Superman 2025

The one they've warmed to with distance; Sean's tentpole of the summer, with David Corenswet, Nicholas Hoult, and Rachel Brosnahan.

28 Years Later 2025

The surprise of the season: a Danny Boyle / Alex Garland reunion with Jodie Comer and Aaron Taylor-Johnson that had them crying, bone temple and all.

'The Naked Gun'85 minutes, in a theater, on purpose

The Naked Gun 2025

Directed by Akiva Schaffer, with Liam Neeson and Pamela Anderson. Both hosts like it and want it to succeed; Sean wishes it were 20% funnier and warns the trailer spoiled half the jokes. Craig calls it the right way to honor IP: keep the style, write your own jokes. Danny Huston is the runaway MVP.

The Naked Gun: From the Files of Police Squad! 1988

The 1988 original, spun off the 'Police Squad!' series with Leslie Nielsen. Sean loves it but doesn't hold it as a sacred text the way he does the Sandler stuff.

Naked Gun 33⅓: The Final Insult 1994

Sean saw it as a birthday movie; its pointed 'Crying Game' gag is the example of a reference that wouldn't land for a 20-year-old today.

Airplane! 1980

The Zucker-Abrams-Zucker template, the joke-a-minute spoof this reboot descends from.

Top Secret! 1984

Grouped with 'Airplane!' as the ZAZ house style Sean was raised on and misses.

Popstar: Never Stop Never Stopping 2016

Shaffer's Lonely Island movie, cited to argue he's one of the few genuinely good comedy directors of the last 15 years. The snowman love-montage in 'The Naked Gun' is classic Lonely Island and was almost cut.

Hot Rod 2007

The other underrated Shaffer comedy in his corner.

The Big Heat 1953

The kind of hard-boiled 50s-60s procedural the spoof is straight-facing, which is why Seth MacFarlane insisted on real actors, not comedians.

Together 2025

The Dave Franco / Alison Brie horror film sharing the weekend Sean liked, part of the varied, healthy moviegoing slate.

The Fantastic 4: First Steps 2025

In its second weekend, one leg of the spread-out box office Sean says looks like the moviegoing he remembers.

The Bad Guys 2 2025

The animated sequel rounding out the weekend, Sean's Saturday plan with his daughter.

Mission: Impossible - Fallout 2018

The falling-walls fake-hospital gag with Kevin Durant reads as a 'Fallout' callout, per Amanda.

The 21st-century comedy crisiswhy the studio comedy nearly vanished, plus Craig's 10 most significant of the last 25 years

Anchorman: The Legend of Ron Burgundy 2004

On Craig's top 10; he grants it's a very 30-year-old-white-guy list.

Superbad 2007

On Craig's top 10; his measuring stick for staying power.

The Hangover 2009

On Craig's top 10, and the only pure original comedy in the all-time live-action grossers. Sean remembers the opening-weekend theater as anarchy, like a Kendrick Lamar concert.

The 40-Year-Old Virgin 2005

On Craig's top 10; he rewatched it recently and found the humor holds, but now sees the same jokes done free online.

Talladega Nights: The Ballad of Ricky Bobby 2006

On Craig's top 10.

Wedding Crashers 2005

On Craig's top 10; named as a movie you weren't 'allowed' to enjoy the same way during the sensitive years.

Bridesmaids 2011

On Craig's top 10.

Step Brothers 2008

On Craig's top 10.

Meet the Parents 2000

On Craig's top 10, and, he notes, De Niro proving a great actor can make a comedy.

Mean Girls 2004

The one Amanda was nervous he'd forget; saved for last.

Girls Trip 2017

Sean's add to widen the aperture beyond the white-guy list.

Barbie 2023

The 2020s comedy line they can actually quote ('Do you guys ever think about dying?'). Sean calls it gaming the system, huge IP elevated by talent, and still ranks it third on his Greta Gerwig list.

21 Jump Street 2012

Floated for the list; Craig thinks its staying power hasn't held up next to the Apatow-era hits.

Game Night 2018

Loved but, they agree, didn't stick around.

Zoolander 2001

Sean's personal, generational add, and one of the comedies honored in the theater's 'save the comedy' pre-roll.

Ocean's Eleven 2001

The one Craig wondered about counting as a comedy; funny, but no.

Ted 2012

Sean's loudest-ever theater; a ~$500M original comedy that belongs on the list. Its bear is now so expensive to render that the sequel and TV show are in doubt.

Deadpool & Wolverine 2024

No. 2 on the all-time live-action comedy grossers: evidence the money now flows to IP, not original jokes.

Deadpool 2 2018

No. 4 on that same all-time list.

Deadpool 2016

No. 5 on that list.

Hi, Mom 2021

The No. 3 all-time comedy grosser, a Chinese film that made about $840 million, the kind of hit that never enters the American conversation.

Detective Chinatown 3 2021

No. 6 on the all-time list, another Chinese blockbuster.

Men in Black 3 2012

No. 7 on the all-time list.

Men in Black 1997

No. 8 on the all-time list.

The Hangover Part II 2011

No. 9 on the all-time list.

The Mermaid 2016

No. 10 on the all-time list, another Chinese comedy.

No Hard Feelings 2023

The Jennifer Lawrence comedy Sean respects: proof she can do the thing few prestige ingénues will.

That Awkward Moment 2014

The Michael B. Jordan / Miles Teller / Zac Efron comedy dredged up as the example of a serious actor taking a comedy swing.

Clueless 1995

One of the older titles the theater's pre-roll had to reach back for to fill out the 'save the comedy' reel.

Sinners 2025

Sean's argument for why a movie still matters: make 'Sinners' and you're part of a phenomenon people never forget, unlike a refillable spoof.

Not films filtered out: TV, games, ads

TV Police Squad!Modern FamilyThe Morning ShowFamily GuyAbbott ElementaryTiresThe BearTed (series)Saturday Night Live

Podcasts The RewatchablesThe TownJam SessionNo Laying UpThe Ringer Fantasy Football Show

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