The Big Picture Podcast Episode Summary: ‘Happy Gilmore 2,’ ‘The Naked Gun,’ and the 21st-Century Comedy Movie Crisis

Release Date: August 1, 2025

Hosts and Guest:

• Sean Fennessey (Host)
• Amanda Dobbins (Co-host)
• Craig Horlbeck (Guest, Host of The Ringer Fantasy Football Show)

Introduction and Episode Overview

[00:00 – 01:28]

The episode begins with Sean Fennessey delivering a brief advertisement for Apple Pay. Transitioning into the main content, Amanda Dobbins introduces the episode's focus: discussing sequels to iconic Gen X comedies—'Happy Gilmore 2' and 'The Naked Gun' reboot—and examining the broader decline in comedy movies.

Sean Fennessey [00:38]:

"On today's episode, we are discussing two follow-ups to some legendary Gen X comedy IP, Happy Gilmore 2 and the Naked Gun reboot. We'll also be talking about this century in comedy movies. What the hell happened to them?"

Casting News and Concerns

[02:09 – 05:00]

Sean shares news that Celine Song, known for 'Past Lives' and 'Materialist,' has been tapped to write a sequel to 'My Best Friend's Wedding'—a beloved rom-com. Amanda expresses mixed emotions, fearing it might follow the trend of underwhelming remakes but remains cautiously hopeful.

Amanda Dobbins [02:38]:

"I hear from roughly 30 people in my life about this... I just hate it, but what if I don't hate it? What if I don't?"

'Social Network 2' and Casting Shifts

[06:00 – 15:00]

The conversation shifts to 'Social Network 2,' highlighting that Jesse Eisenberg will not reprise his role as Mark Zuckerberg. Instead, Jeremy Strong is being considered. Amanda voices concerns about the absence of key figures like David Fincher, fearing the film's quality may suffer without Eisenberg's involvement.

Amanda Dobbins [06:33]:

"I just... I am begging Aaron Sorkin to consider a group project."

Sean Fennessey [13:06]:

"Jeremy Strong is yet one more person who needs a group project. Do you know what I mean?"

Craig remains cautiously optimistic about the talented new cast but echoes Amanda's apprehensions.

Deep Dive into 'Happy Gilmore 2'

[15:00 – 35:50]

The hosts critically evaluate 'Happy Gilmore 2,' directed by Kyle Newcheck and written by Tim Herlihy and Adam Sandler. Craig vehemently criticizes the film as the "worst movie" he's ever seen, labeling it as "lazy fan service" laden with cameos that lack depth.

Craig Horlbeck [17:26]:

"I thought this was genuinely maybe the worst movie I've ever seen. It was the laziest fan service pandering, nostalgia bait I've ever seen."

Amanda concurs, noting the film's reliance on golf personalities and personal elements tied to Adam Sandler but admits to finding some entertainment in it.

Amanda Dobbins [18:50]:

"I didn't think this movie was a good comedy, but... I had a decent time watching the whole thing."

Sean offers a more nuanced perspective, suggesting that while the movie is flawed, it attempts to blend serious themes with comedy, offering a unique, albeit imperfect, contribution to American filmmaking.

Sean Fennessey [20:49]:

"Can a movie be bad and wonderful at the same time is an important question to ask."

'The Naked Gun' Reboot Analysis

[37:35 – 50:00]

Turning to 'The Naked Gun' reboot, the hosts discuss its efforts to maintain the original's comedic style. Craig praises the film for respecting the original IP while introducing new jokes and a fresh cast, including Liam Neeson and Pamela Anderson.

Craig Horlbeck [45:10]:

"I thought this is the right way to honor IP where you keep the style but you make it your own."

Amanda shares her limited exposure to the franchise, appreciating its comedic moments despite recognizing its departure from her usual comedy preferences.

State of Comedy Movies Today

[44:00 – 71:40]

The discussion broadens to the overall decline in quality and originality within Hollywood's comedy genre. The hosts lament the shift away from communal comedic experiences in theaters towards niche, meme-driven humor prevalent on streaming platforms and social media.

Sean Fennessey [63:31]:

"You can get it at a stand-up comedy show, but otherwise you can't get it looking at your phone."

They highlight the absence of influential figures like Judd Apatow, who historically revitalized comedy through writing and producing, and express the need for a cultural figure to spearhead a revival of quality comedic films.

Sean Fennessey [64:15]:

"I think you need a person who is a culture-changing person."

The conversation touches on challenges faced by modern comedians in transitioning to movie-making, emphasizing the financial risks and changing audience behaviors.

Craig Horlbeck [71:23]:

"I don't think comedy is bad now. I think there's great comedy. There's almost too much of it."

Closing Remarks and Future Outlook

[71:00 – End]

In conclusion, the hosts reflect on the future of comedy movies, balancing optimism for potential revivals with concerns over current industry trends. They hope for a resurgence of quality comedies that can resonate both theatrically and culturally.

Sean Fennessey [71:37]:

"Thank you to Craig... We'll be back next week with a summer movie mailbag. We'll see you then."

Notable Quotes with Timestamps:

• Sean Fennessey [04:08]:

  "They're going to work. They're going to make a little bit of money. They're going to get a lot of Netflix views, but this is just slapping a band aid on a larger problem that is not being fixed."

• Amanda Dobbins [03:12]:

  "I’m reclaiming Materialists. You and I are on that project together."

• Sean Fennessey [20:49]:

  "Can a movie be bad and wonderful at the same time is an important question to ask."

• Craig Horlbeck [17:26]:

  "I thought this was genuinely maybe the worst movie I've ever seen. It was the laziest fan service pandering, nostalgia bait I've ever seen."

• Amanda Dobbins [18:50]:

  "I didn't think this movie was a good comedy, but... I had a decent time watching the whole thing."

• Sean Fennessey [71:37]:

  "Thank you to Craig... We'll be back next week with a summer movie mailbag. We'll see you then."

This summary encapsulates the primary discussions, insights, and critical perspectives shared by Sean, Amanda, and Craig throughout the episode. It highlights their concerns about the current state of comedy movies, their analysis of recent sequels and reboots, and their hopes for the future of the genre. Notable quotes are interspersed with timestamps to provide context and emphasize key moments in the conversation.