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Episode #784: Vanilla Sky (Patreon)

Published:
2025-02-11 05:00:02
Edited:
2025-08-21 18:46:00
Imported:
2026-06
Tags:

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Content

“This is a version of New York that died immediately on 9/11” - Steve, on the film’s vibe

On this episode, WAIT-WHUT-uary continues with a chat about the early-aughts Cameron Crowe psychological thriller, Vanilla Sky! How amazing is all this New York City cinematography? Was this one of the last times Tom did some super-serious dramatic acting? Can we get more Kurt Russell characters like this doctor guy? Can we also just get Jason Lee back in movies? Has Cameron Diaz ever been better? And how creepy is that mask? PLUS: Coming this Fall to Paramount+, Klingon Frasier!

Vanilla Sky stars Tom Cruise, Penélope Cruise, Cameron Diaz, Jason Lee, Noah Taylor, Timothy Spall, Tilda Swinton, Michael Shannon, and Kurt Russell as Dr. McCabe; directed by Cameron Crowe.We hope you are enjoying Ad-Free WHM! Thanks so much for being the kick-ass Patreon subscriber that you are—your support keeps the lights on around the old clubhouse and allows us to continue doing these shows! We know you have a lot of options for podcast enjoyment and we're stoked you chose to spend some time with us!

Don’t forget to snag your tickets for the replay of our Ghostbusters: Frozen Empire show and the After Party Q&A that followed! The replay’s available now through Thursday, February 13th!

Tickets are on sale now for our three-night residency during the Oxford Comedy Festival! We’ll be doing six shows over three nights from July 18 through 20, doing shows like WHM, W❤️M, The Nexus, The Gleep Glossary, and Animation Damnation! Tickets are going fast, so friends over there, snag your tix! 

Throughout 2025, we’ll be donating 100% of our earnings from our merch shop to the Center for Reproductive Rights. So head over and check out all these masterful designs and see what tickles your fancy! Shirts? Phone cases? Canvas prints? We got all that and more! Check it out and kick in for a good cause!

Original cover art by Felipe Sobreiro.

Files

Comments

Jeremy Pawlak

Can't wait to give it a listen! I remember really liking the movie (and the catchy McCartney title track) back when it came out, perhaps this is the excuse I need to re-watch.

Busiris

Really with Andrew on the whole Tom Cruise coconut cake thing because every time I hear about it, I think about how badly I want Tom to send me a cake every year, how nice! The challenge is to get on his good side, but my problem is that he terrifies me. As much as I love him as an actor, he's a scary dude. Just watch Tom's demeanor shift in that video of the guy that squirts him with water on the red carpet. I'd fold like cheap paper if he ever talked to me like that.

Taco6N 13

It's been awhile since I've seen it, but I remember Cruise being really good in Obilivion.

Ray

Cameron Diaz scary

The Mad Jay Woman

This is too crazy - was just thinking about this movie and wondering if any of my pod feed had previously covered it and now low and behold! My WHM synergy is nearing completion… Basically I would like to opt in to a fantasy coma but sadly even in the Vanilla Sky reality capitalism still makes that accessible only to the privileged so I guess it’s back to building guillotines…

WarOfTheBees

Blank Check covered this as well if you're looking for more Vanilla Sky content!

WarOfTheBees

Russell was on another level in this movie. The part where the guy tells him he's a construct and he insists he's real is fantastic.

Eren Keskin

The original is better for sure, and the mask in that is actual nightmare fuel. Very skin-like. Tom Cruise is at his best when he plays villains, and since he plays a billionaire douchebag in this, I consider it a villain role. Btw, as your Turkish patron, I'm appointing Andrew as the mayor of New York. We have Ghostbusters on our payroll too. A ghost-suck machine doesn't come cheap, you see. Those Tribeca boys will rebrand themselves as Kebabbusters soon, of course.

James C Harris

Well now I just want Klingon Frasier!

Jamie

2001 was the year I took my only college film course, and I thought this movie was the third best thing I saw that year, only behind Memento and The Royal Tenenbaums. But unlike those two, I have not rewatched this in a very long time.

MarkNM

DID SOMEBODY SAY GHOST SUCK? -Dan Aykroyd --ngyah ngyah ngyah

MarkNM

Yalls NEED to do Rock of Ages. That movie makes The Apple look like Rodgers & Hammerstein.

Gone

Did you guys really talk about late 90s cum movies while talking about a movie with Cameron Diaz and not even mention Something About Mary?

Tony King

I heard about the Tom Cruise cake on the Empire magazine podcast. They get one every year, and supposedly it's really good!

Tala Hobballah

Death Proof was advertised as feminist and then they SELL THEIR FRIEND FOR A CAR. I wanted everyone to crash and burn at the end.

Samuel McGuire

I heart my WLM boys when they disagree and we get that ball-busting 🤩. Honed over the decades of friendship. Just beautiful.

DMAC

Michael Shannon's Shit House Grand Opening adjacent to The Gettin' Place.

WarOfTheBees

Cameron Diaz is an actor that deserves a lot more respect. I think she was written off early on as a pretty face and as a result no one really worked on her acting talent...but when you see her in the right roles she really shines.

Dennis Stack

Totally forgot about the Spielberg cameo in this one, which led to me thinking, "wait, didn't Crowe cameo in a Spielberg movie once?" He did. In Minority Report. With Tom Cruise, the exact same year. What a weird exchange.

Moe Tilden

Almost Famous is based on a true story of when Crowe was working for Rolling Stone as a teenager and tried to interview a grieving, coked up, paranoid Greg Allman. So no Eric, it's not "just another boomer jerking off to the 70's " lol. It's authenticity makes it go from a music fan road trip movie to a beautiful story about growing up painfully awkward and out of your depth. One of my favorites that movie.

Jonnie Sea

WWF New York appearing in this film is so 2001…and ALL THE RIGHT FRIENDS is just the ELEC MAN theme from Megaman 1

Nexuscrawler

20+ years later sigor ros remains one of my favorite bands. Starting from this grabbing this movie from old school Netflix

Tala Hobballah

"You smooth fuck!" Lmao I love characters that get that kind of reaction out of me.

Calikusiolek

Ichi the Killer - best use of cinematic ejaculate

I.C. Weiner

Chris mentioned Minority Report and how the ending didn't sit right with him because it should have ended when he goes down into the hole and instead he gets a happy endong. Well, this just happens to be my favorite film theory and it is the kind you guys hate. The movie tells you earlier that the capsule thing has you in a vivid dream and the film filter changes for the happy ending. That's right, the ending was all a dream!

Exambolor

This was my first time watching this movie and I think I went “Wait…WHUT” multiple times during the viewing, because this film is a perfect example of it

Z

Crowe's worldview is very specific to Generation Jones (the latter-day boomers born from the mid 1950s to the early 60s). He shared the tastes boomers had, but he was also a lot more aware of what was happening with Gen-X -- he made Singles before the broader public became aware of grunge, for example.

RJ Cunningham

Anyone else have no clue Karl Urban is going to be Johnny Cage in Mortal Kombat 2?

Jason

Wait, whut?

Jason

Seems like an odd choice but as a full fledged Urbanite I’m willing to give it a chance.

Smaug

I don't buy Jason Lee in any way shape or form being romantically involved with Penelope Cruz unless he specifically brought her to the party to be cuckolded by Tom Cruise

AlsoNamedB0rt

Anyone know if we got clear audio of each guy saying “I swallowed your cum” I need to make some new ringtones…

Louis Brooks

I have a love/hate relationship with this movie. It's not the best on how women are represented. That's just me. However the scene in Central Park where Sophia jumps on David is very a cute meet up and then he knows he's dreaming is a beautiful but gut wrenching scene.

Rose Esposito

The conversation about all the cum-heavy movies of the late '90s and early '00s reminded me of the classic "was the projector broken??" moment from the beginning of the Shrek episode. Now I have to go back and listen to that yet again. <3 also I have a distinct memory of my mom going to see Vanilla Sky while my little pals and I went to Monsters Inc. 😬 She did not share her thoughts with me that day.

Trev Herron

Glad this gave me an excuse to finally watch this one after so long. I don't love it but it was definitely worth a watch, Cameron Diaz is really great and surprisingly sinister. Solid ass cast. It's a soundtrack movie (and every movie feels like a soundtrack movie now imo) but it's definitely a very good soundtrack. It's always kind of embarrassing when you discover old hits and love them and be like "have you guys heard this Solsbury Hill song? Pretty great!" like 40 years post facto lol.

Justin

I really really wish I could end 2025 by just screaming "TECH SUPPORT!!!!!" at the top of my lungs.

Justin

Maybe I'll just make a request to every person I meet from now on "hey if you don't mind could you just really quick yell 'tech support' for me to see if we're in your waking nightmare? Thanks."

RJ Cunningham

I know Cabin is rightfully big on Swinton and Michael Clayton, after a rewatch, is her delivery of “you don’t want the money?” up there first best singular acting moment of the decade? Up there with the Plainview “abandoned my boy” delivery A great I Love Movies Month would be the 2007 movies you haven’t covered yet (No Country, Eastern Promises) and then definitely don’t do Juno. Assassination of Jesse James seems to be an under-seen movie

Craig

I read a lot of Philip K Dick stories in my youth but not this one, so I assumed when I saw the movie that the original story would end, in typical Dick fashion, with him finding the pictures of his kid and killing the guy. As it turns out the story is way more different to the movie than that.

Nathan Foley

Watched this movie for the first time last night, and that was preceded by a rewatch of Lost Highway two nights ago. Jason Lee tells him, "You're in OJ land, man!" and now I'm wondering how influenced Crowe must have been by Lynch in making this.

Kevin Matthews

Sorry to be so late to comment, and sorry if this has already been mentioned, but I think I recall you going on about the regular inclusion of William Mapother in Tom Cruise movies. Mapother is, IIRC, Cruise's cousin, and Tom Cruise would be Thomas Cruise Mapother IV if he used his full name.

Billie Jackson

Bryan Johnson is the youth obsessed billionaire. Had to look him up because I did not remember him and so was thinking of Peter Thiel and his blood transfusion from twinks thing. Was wild to hear my deadname on whm.