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