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1.
One night a week or month when the bars (usually in college towns) charge a cover and then let patrons drink all the cheap beer they can. You have to get there early to get a pitcher or you're out of luck, they go fast.
"Hey are you going to Dill tonight?"
"Nah, I'm kinda broke, I'm headin to the Madhatter for penny pitchers!"

"Hey, I heard you coming in at 5am through the window, did you puke in the microwave...!?"
"Ohh maybe...I dunno..I went to penny pitchers..."
by lono1807 June 03, 2009
 
2.
Someone who does not care for pennies and leaves them on the ground somewhere. rich

Someone who leaves pennies (heads up) hoping others will get good luck from picking it up. thoughtful

Someone who considers throwing pennies at unexpected victems a sport. asshole
"Stop being a penny pitcher, a penny saved is a penny earned."

"What are you doing?"
"Making someone's day!"
"Aw, that's so cute I want to punch you."

"Look at that asshole queer, let's throw pennies at him."
by Robert Oldhead November 03, 2007