It is a truth universally acknowledged that a single person in possession of a chat-up line, must be in want of… well, something.
Films are full of them: characters who attempt to exert their charisma in order to charm their way into another’s heart.
But, the fact of the matter is, even the smoothest character has a hard time pulling off a chat-up line.
In fairness, some are better than others – for instance, James Stewart’s attempts land quite well in Frank Capra’s You Can’t Take It With You (1938), while Humphrey Bogart and Ingrid Bergman prove chat-up pros in Michael Curtiz’s classic Casablanca (1942).
Below, we’ve highlighted the 15 most embarrassing, hilarious and, yes, crude, examples.
Anchorman: The Legend Of Ron Burgundy (2004)
Ron Burgundy (Will Ferrell): “I don’t know how to put this, but I’m kind of a big deal.”
Austin Powers: The Spy Who Shagged Me (1999)
Austin Powers (Mike Myers): “Let me ask you a question. And be honest. Do I make you horny, baby? Do I? Do I make you randy?”
Couples Retreat (2009)
Dave (Vince Vaughn): “Someone has to call God and tell him that one of his angels is missing.”
Face / Off (1997)
Castor Troy as Sean Archer (John Travolta): “I hate to see you go, but I love to watch you leave.”
Gone with the Wind (1939)
Rhett Butler (Clark Gable): “I don’t think I will kiss you, although you need kissing, badly. That’s what’s wrong with you. You should be kissed and often, and by someone who knows how.”
The Hangover (2009)
Phil Wenneck (Bradley Cooper): “Ma’am, in the leopard print dress, you have an amazing rack.”
Alex “Hitch” Hitchens: “I couldn’t help but notice that you look a lot like my next girlfriend.”
Intolerable Cruelty (2003)
Miles Massey (George Clooney): “Your husband told me you were the most beautiful woman he’d ever seen, but he didn’t say anything about the most beautiful woman ID ever seen.”
Leaving Las Vegas (1995)
Ben Sanderson (Nicolas Cage): “I really wish that you’d come home with me. You’re so cute and I’m really good in bed, believe me.”
National Lampoon’s Van Wilder (2002)
Van Wilder (Ryan Reynolds): “Are you stalking me? Because that would be super.”
PS I Love You (2007)
Gerry Kennedy (Gerard Butler): “I know what I want, because I have it in my hands right now. you.”
Tony Montana (Al Pacino): “You’re good-looking. You got a beautiful body, beautiful legs, beautiful face, all these guys in love with you. Only you’ve got a look in your eye like you haven’t been f***ed in a year.”
The Sure Thing (1985)
Walter Gibson (John Cusack): “How would you like to have a sexual experience so intense it could conceivably change your political views?”
Vanilla Sky (2001)
David Aames (Tom Cruise): “See, I’ve got this little problem. I’ve got a stalker… I need a cover. I need for you to pretend we’re having a scintillating conversation, and you are wildly entertained.”
Thelma & Louise (1991)
JD (Brad Pitt): “I may be an outlaw, darlin’, but you’re the one stealing my heart.”