The Pick-Up Artist

[it is the EIGHTIES]
Robert Downey, Jr.: Check me out, man. I am AWESOME. Hey, ladies, you want some? Do ya?
Some Girl: Okay, here's my number.
[he CROSSES the street and LITERALLY attempts to PICK UP another girl IMMEDIATELY]
Vanessa Williams: Can't you see that I am walking my dog and also too cool for you? Go away.
[he goes to SOME CLUB and hits on Victoria Jackson to MAKE SURE everyone knows this movie is from the EIGHTIES]
Harvey Keitel: Get away from my girl. I am a gangster, as evidenced by this pervy mustache. Do not tangle with me.
Robert Downey Jr.: No problem, man, no problem. But by "tangle with you," I hope you don't mean "try to pick up this girl whose dad owes you some money and is therefore attempting to work out some sort of deal wherein she is traded to the warden from Shawshank Redemption to pay off her father's debts," because that's JUST what I'm about to do.
[he DOES]
Molly Ringwald: You think you're cool? Well, I shall prove you wrong! Let's go have sex in your car.
Robert Downey, Jr.: Wha-- this usually doesn't work this well. I am baffled.
[they BONE in his CAR and then she DESERTS him to go be a TOUR GUIDE at the Natural History Museum]
Robert Downey Jr.: This woman has intrigued me. I must follow her in a creepy, but sort of endearing manner.
[he FOLLOWS her HOME to Coney Island and YELLS at her WINDOW]
Molly Ringwald: God! What are you doing here? We already had sex, what more could you possibly want? Fine, come upstairs.
Dennis Hopper: Hellloooooo! I'm wasted. Want some eggs?
Robert Downey, Jr.: Wow, your boyfriend seems...nice.
Molly Ringwald: Yeah...my boyfriend. That's who he is. And he owes a lot of money to some very bad dudes, so maybe you should go. Also, I have intimacy issues!
Robert Downey, Jr.: You do? Me too!! Maybe we can work them out together after we save your dad.
[she goes to ATLANTIC CITY to try and WIN all the money, but FAILS after having come SO CLOSE]
Robert Downey, Jr.: Why don't you gamble on me?* I mean that in a literal sense.
[he SELLS his CAR and they put the PROCEEDS on two ROULETTE numbers and WIN]
Molly Ringwald: I guess you are an okay guy.
Dennis Hopper: Wooooooooooo!!! Still wasted!!