This week, sail away with Every Rom Com, as we discuss the first of two sports rom coms we’ll be covering from director Savage Steve Holland, “One Crazy Summer.” We’ll dig into Holland’s career as well as Demi Moore’s, talk about our favorite bits from this cult classic, and learn a little about the sport of sailing! We’re joined by two returning guests: artist and author Ryan Estrada, who helps us unpack the movie’s animation sequences, and musician and appreciator of absurdist humor, David Rosen of the Piecing it Together podcast. You won’t want to miss this boat! 

0:00-12:03 Welcome Back Guests Ryan Estrada and David Rosen, Favorite Sports Movies

To See Ryan’s Work:

ryanestrada.com 

Follow Ryan on Social Media:

Bluesky: https://bsky.app/profile/ryanestrada.com 

Instagram: https://www.instagram.com/ryanestradadotcom/?hl=en 

Hear Ryan Talk About “Jerry Maguire”: https://www.everyromcom.com/podcast-1/episode/32b40295/every-rom-com-25-jerry-maguire 

Find David’s Work:

bydavidrosen.com 

Follow David on Social Media:

Twitter: https://x.com/PiecingPod 

Facebook: https://www.facebook.com/groups/piecingpod 

Instagram: https://www.instagram.com/piecingpod/?hl=en 

Bluesky: https://bsky.app/profile/piecingpod.bsky.social 

12:03-21:30 TRAILER, Basic Info, Interesting Facts

More Info On “One Crazy Summer”:

https://www.insidehook.com/film/director-steve-holland-cult-classic-better-off-dead-john-cusack 

https://ew.com/article/2011/08/02/better-off-dead-blu-ray/ 

https://www.youtube.com/watch?v=etvtelWqQTY 

https://robertvgalluzzo.com/savage-steve-holland/  

21:30-30:10 General Opinion

30:10-46:30 Cast & Crew In-Depth

More Info on Savage Steve Holland:

https://www.fastcompany.com/3055116/the-long-strange-journey-of-better-off-dead-director-savage-steve-holland 

Speech Bubble podcast interview: https://www.youtube.com/watch?v=E-AOhxjUPzA https://robertvgalluzzo.com/savage-steve-holland/ 

More Info on Demi Moore:

https://www.biography.com/actors/demi-moore

https://www.interviewmagazine.com/culture/new-again-demi-moore 

https://www.britannica.com/biography/Demi-Moore 

https://people.com/demi-moore-sober-companion-st-elmos-fire-brats-documentary-8660334 

Demi Moore’s acceptance speech “The Substance”: https://www.youtube.com/watch?v=udQVLYra8sU 

46:30-58:47 Opening Animation Sequence, High School Graduation

58:47-1:17:25 Cassandra, Arrival in Nantucket, Intro to Weird Ensemble

1:17:25-1:25:11 Evil Real Estate Developer Plot, Cassandra And Hoops Hang Out, Wacky Beach Time

1:25:11-1:35:22 Drive-In Movie and Godzilla Party Shenanigans, Confrontation With Teddy

1:35:22 SPOILERS BEGIN

1:35:22-1:46:37 Helping Cassandra Montage, Revenge on Teddy, Cassandra’s Concert, Setbacks

1:46:37-1:56:37 Regatta Plan Begins, Ryan’s Regatta Story, Random Sailing Facts

More Info On Sailing:

https://www.sailing.org/tools/documents/RRS20212024Finalwithbookmarks-[27255].pdf 

https://insailing.com/blog/everything-you-need-to-know-about-regattas 

1:56:37-2:11:56 The Regatta, End Of the Movie, Sports Movie Tropes In “One Crazy Summer”, Puzzle Pieces

2:11:56-2:21:46 Double Feature Recommendations