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1.
A characteristic, mannerism, or appearance of a person, either subtle or overt, which implies unique, eccentric, creative, adventurous or unconventional thinking.
David Crosby refers to long hair as a freak flag in his song Almost Cut My Hair. "I feel like letting my freak flag fly."

Movie Character Ben compliments Meredith in The Family Stone, "You have a freak flag...you just don't fly it."
Por Anthony T. White 22 de mayo de 2006
 
2.
Letting loose, being down with your cool self, especially in front of a group of strangers. Your inner freak, that wants to come out, but often is supressed, from social anxiety.
Ang: "Hey T-Rev, whatcha doin this weekend bra?"

Trev: "Ang, I'm gonna fly my freak flag!"
Por Freaky Ang 08 de mayo de 2006
 
3.
Unrestrained, unorthodox or unconventional in thinking, behavior, manners, etc. One who espouses radical, nonconformist or dissenting views and opinions that are outside the mainstream.
When traveling through the bible belt of the US, it's best not to let your freak flag fly high. Otherwise, you'll be harassed and attacked by these backwater, backward thinking theocrats.
Por Preston Pierce 11 de marzo de 2011
 
4.
The labia minora that protrude so much so, that they flap in the wind like the good ol' flag!
AKA: Bacon Gliders, Pastrami Box, Roast Beef Curtain.
At the nude beach, Shelly had no problem letting her freak flags flap in the breeze.
Por Princess Freak Flag 10 de mayo de 2010
 
5.
1.) David Crosby's penis
2.)Jimi Hendrix's penis
David Crosby: "I feel like letting my freak flag fly"
translated to "I'm going to have sex with mad bitches because it's the 60's and I can"

Jimi Hendrix: "But I'm going to wave my freak flag high...HIGH"
translated to "I have a massive erection"
Por freakflag 03 de abril de 2010
 
6.
1. Your inner party animal. "Letting your freak flag fly" means acting wild. See crazy.
2. An unsigned shock-metal/industrial metal band from Canada.
1. I'm gonna let my freak flag fly!
2. Dude, Freak Flag is fuckin' awesome!
Por That Stupid MF 01 de septiembre de 2007
 
7.
A flag, of sorts, strung up a pole at an outdoor concert/festival to signify where your seats are.
Our freak flag was so cool, i could find my buds no matter what i was on.
Por Charles L. 03 de mayo de 2006