this refers to the name that Matt Bailey received in early September of 2009. He goes by Bossman Bailey when he defeats less competent people in bowling by one pin, even though it was only the fourth time the Bossman had played in his life. The Bossman Bailey rules over The Boss and all other Boss-like references
by dragonbasketball43 October 5, 2009

when a girl masturbates during a movie while with her bestfriend then proceeds to look up pornography in barns and noble :)
by crazyazzbiatch January 9, 2011

Pure-feltcher
by jonny doesnt know November 21, 2010

The coolest person you can think of. This chick is so gorgeous. They all want her. She'll be famous one day
by My Fake Name March 28, 2014

bum-bailey is a phrase coined by Shakespeare, and most recently coming into prominence as a term widely used on the www.peepsplace.com forum to describe a poster using the screen name Dave "The Meatman" Scandaliato, who portrays himself as a homosexual gambling tout frequenting cheap hotels in Las Vegas.
I'm not scared to wear a woman's thong, bum-bailey, I just have the minimum sense of self esteem not to do it.
by Doodles 1947 June 23, 2014

Someone who will be your best friend for the longest time and one day you’ll start to realize you have feelings for him. He can be a bitch sometimes but he will love you very much. He is hot, tall, athletic, and sweet.
by bitchy_bitch May 21, 2019

by urmumgae6969 December 23, 2019
