Mistakes
When Roy is lying on the sofa whilst talking on the phone to his ex-girlfriend, the telephone disappears. At the end of the call he puts the telephone on his chest, but the telephone is not there in the next shot. See more...
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Molly: Is this normal for him?
Earl: Well, the words "normal" and "him" don't often collide in the same sentence.
Roy 'Tin Cup' McAvoy: Do you find me sexy?
Dr. Molly Griswold: You have your moments.
Roy 'Tin Cup' McAvoy: Well, you let me know which moments are my moments and I'll try and duplicate 'em.
Roy 'Tin Cup' McAvoy: If I had it to do all over again, I'd still hit that shot.
Romeo: Man, you'd bury yourself alive just to prove you could handle the shovel.
Dr. Molly Griswold: I'm a, like, terrible shrink, probably. I should have never gotten out of real estate, shit, actually, I should have never left Ohio for that cowboy in Amarillo, but... Have you ever been to Amarillo?
Roy 'Tin Cup' McAvoy: Cowboy?
Dr. Molly Griswold: Yeah. It's not as romantic when you're actually with one, trust me.
Dr. Molly Griswold: I find him... mildly attractive when he's obnoxious and arrogant like this.
Romeo Posar: Oh, good. That's his best side.
Romeo Posar: Now THAT was a defining moment. And the definition was "shit."
Romeo Posar: Look, boss, I only got one rule. And that's never bet money that you don't have on a dog race with an ex-girlfriend who happens to be a stripper.
Doreen: You're not one of those women who tries to fix men, I hope. I mean, men cannot be fixed, and especially him.
Roy 'Tin Cup' McAvoy: I assume I have the confidentiality of the doctor-client privilege in regards to this outfit?
Roy 'Tin Cup' McAvoy: You know why I still hit that shot?
Romeo Posar: Yeah, because it's the only way you could beat Dave Simms.
Roy 'Tin Cup' McAvoy: No.
Romeo Posar: 'Cause it was that look in your face...
Roy 'Tin Cup' McAvoy: I hit it again because that shot was a defining moment, and when a defining moment comes along, you define the moment... or the moment defines you.
Dr. Molly Griswold: There's no such thing as semi-platonic.
Roy 'Tin Cup' McAvoy: Well there ought to be.
Roy 'Tin Cup' McAvoy: When was the last time you took a risk?
Dr. Molly Griswold: Well, I'm with you, Roy. I'm with you.
Roy 'Tin Cup' McAvoy: Sex and golf are the two things you can enjoy even if you're not good at them.
Earl: You the man, Roy. You are definitely the man.
Clint: The man needs a ride home.
Molly: Why do men always insist on measuring their dicks?
Roy 'Tin Cup' McAvoy: This is for Venturi who thinks I should lay up.
Romeo: What does he know? He only won this tournament before you were born.