Jack: Listen, honey. Let me call you right back. Miles and I are in the middle of something. No, it's nothing serious, Miles is just having one of his freak-outs. Yeah. Love you too.
 • Movie: Sideways • Rating: Unrated • Permalink

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Miles Raymond: Hey, what should I wear?
Jack: I don't know, something casual but nice. They think you're a writer.
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Jack: Try to be your normal, humorous self. The guy you were before the tailspin. Do you remember that guy? People love that guy.
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Jack: Consult your doctor before using this product. Side effects may include oily discharge, hives, loss of appetite, low blood pressure. If you have diabetes or a history of kidney trouble, you're dead, asshole!
 • Movie: Sideways • Rating: Unrated • Permalink

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Cammi: And here are your handy wipes.
Jack: Oh, so that's what these are. For a minute there I thought you guys were promoting safe sex.
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Jack: [Stephanie pours Jack and Miles full glasses of sample wine] Oh, Stephanie, you bad girl.
Stephanie: I know, I need to be spanked.
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Jack: I'm trying to get you laid, I'd appreciate a little help!
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Miles Raymond: Okay, so what's the plan?
Jack: Uh... the plan is... you go.
Miles Raymond: ME?
Jack: 'Cause of my ankle. Still hurts. Just go explain the situation, Miles.
Miles Raymond: [laughs uproariously]
Miles Raymond: Explain the situation? Yes. 'Excuse me, sir, my friend was the one balling your wife couple of hours ago. Really sorry. He seems to have left his wallet behind. I was wondering if I come in, just poke around, I don't know'
Jack: Yeah, yeah, just like that. That's good.
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Jack: F**king chick's married, man.
Miles Raymond: What?
Jack: Her husband works a night shift or something, and he comes home and catches me on the floor with my c**k in his wife's ass.
Miles Raymond: Oh, Jesus Christ.
 • Movie: Sideways • Rating: Unrated • Permalink

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Jack: Bet ya that chick's two tons of fun. You know, the grateful type?
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