Let Your Freak Flag Fly!

“Some of the times you just gotta let your freak flag fly,” my aunt said to her brother. I didn’t know the context of their conversation, but I didn’t think any definition of this otherwise elusory idiom could remedy any of my dad’s issues. He was a man whose primary goal in life was to fit in, and he did anything and everything he could in life to make that happen. My aunt was the opposite. She did everything she could to stand out as someone hipper and younger. She knew the Billboard Top 40 singles far better than I did at a young age, she wore clothing better suited to younger girls, and she said things better suited to women thirty years younger. This was the first time I heard that particular phrase, however, and even though it involved my aunt’s embarrassing attempt to appear hip, the line stuck with me. I never used it, but when I later heard someone on a hip, top-rated television show say it, I knew something was afoot. Then, one of my friends said it in school, and a week later I began hearing it everywhere.

“Where did you hear that phrase?” I asked my friend from school.

“Dude, I don’t know. I’ve been saying it for decades,” he said. Unbeknownst to me, this response was the key to keeping it cool in the phraseology universe, for no one ever seems to know where they hear them first. To be fair, it can be difficult to remember where we first heard a phrase we’ve been saying for a time, but purveyors of this particular phrase appear to conveniently forget where they heard it to leave the impression that they started it. There’s apparently a lot of prestige wrapped up in starting a phrase, and if someone gets a taste of it, they don’t give it up willingly. Whatever the case is, when obsessively curious types pursue such matters, we often receive everything from blank faces to evasive and defensive responses. Even if the phrase user just started using the phrase last February, those who are evasive and defensive want us to think they’ve been saying it for decades so they can think that, and they dismiss further intrigue on this issue as uncool.

If we found a truly reflective individual who could remember the first time they heard the phrase, it might result in a response to our question as humdrum as, “I think my Cousin Ralphie is da shiznit, and when I heard him say it I wanted his awesome sauce all over me.” If this individual were that honest, they might run the risk of being so over as to be drummed out of the in-crowd, for the clique might deem that confession a violation of the binary, unspoken agreement those in the in-crowd have designed for the world of phraseology. In their world, phrase users want their audience to consider them the originator of the phrase, and anyone who insists on pursuing this line of interrogation runs the risk of being drummed out on an “If you have to ask …” basis.

Another unspoken rule regarding phrases is that we better hurry up and use them as often as we can before a cool cat steps in to declare that the days of using the phrase are now over. “Stop saying that. I’m trying to get the word out that that phrase is over. Tell your friends.” We might be disappointed to learn that we are no longer able to use words, phrases, or idioms that we enjoy using, but we know that when cool people step in to warn us that it’s over, it’s a serious blow in the world of phraseology. We also know that by continuing to use such a phrase, we run the risk of being so over. This begs a question to the arbiters of language who declare they’ve been saying this for decades, how is it that you haven’t encountered someone who declared it so over in that time span? Did you ignore them, and if you did, why should I listen to you?

A work associate of mine attempted to play the role of the foil by correcting me in front of a group of people. “Dude, stop saying that,” he said inadvertently using the tired phrase to end phrases. “I’m trying to get the word out that that phrase is over. Tell your friends.” Anytime we hear someone issue such a condemnation, it is human nature to assume that it’s rooted in something the speaker learned from a person with some authority on the matter. In my experience, however, most of these self-professed arbiters of language consider starting a hip phrase fine but ending one divine. Those with no standing in the hierarchy of cool often take it upon themselves to issue such a condemnation without knowing anything more on the matter than anyone else, but they hope that by pushing us down a notch they might improve their standing in the hierarchy.

Like most of those in the lowest stratum of this hierarchy, I knew nothing about this confusing world of using hip, insider, cool cat language, so I was in no position to question my work associate, but by my calculations this feller was a doofus. He was such a complete doofus that I would no sooner consider seeking advice from him on language than I would dating advice. I still don’t know if this fella assumed a level of authority on this matter based on the idea that he considered me inferior, of if he heard this news from a more authoritative figure, but I decided he did nothing to earn a seat on my personal arbitration board. That situation led me to wonder how we determine our arbiters of words and phrases. My guess is that most people will not heed such advice from just anyone, as that might reveal their status in this hierarchy. My guess is that we make discerning choices based on superficial, bullet point requirements we have for those issuing them? Put another way, if my work associate was more attractive and less chubby, and he wasn’t such a doofus, I may have been more amenable to his guidance on this issue.


For fact checkers, a search return suggests that the phrase “Let your freak flag fly” first appeared in a Jimi Hendrix song If 6 was 9 in 1967. It was later popularized in a David Crosby song Almost Cut my Hair that he wrote for the Crosby, Stills, Nash, and Young album Déjà vu. We can guess that that phrase made its way through the “in-crowd” circuit long before Hendrix or Crosby used it in the song.  

The Urban Dictionary defines “Letting Your Freak Flag Fly” as: “A characteristic, mannerism, or appearance of a person, either subtle or overt, which implies unique, eccentric, creative, adventurous or unconventional thinking.” 2) “Letting loose, being down with one’s cool self, preferred usage to occur in front of a group of strangers. Your inner freak that wants to come out, but often is suppressed by social anxiety.” 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 U.S., it’s best not to let your freak flag fly high. Otherwise, you’ll be harassed and attacked by these backwater, backward thinking theocrats.

Typical Freak Flag Flyers make very specific decisions to avoid titles. They tend to be abstract thinkers who believe they fly high over those of us who believe in nouns (i.e. people, places, and things). Freak Flag Flyers tend to know more about those nouns than the average person, because those people haven’t done their homework. Some Freak Flag Flyers base their outlier status on anecdotal information of these nouns to whom others swear allegiance, on the idea that if we knew what Freak Flag Flyers know, we would be just as sophisticated in our skepticism about allegiances as they are.

Most people fly under a flag: Americans fly under the Stars and Stripes; the Irish fly under the Irish tricolor; and the British fly under the Union Jack. There are some people, however, who fly under no flag, and they provide this information to anyone who asks, and some who don’t. Don’t expect them to admit to flying under a freak flag either, for the very essence of flying under a freak flag is designed to give its flyer an open-ended, free lifestyle persona that doesn’t conform to societal definitions such as definition or allegiance … Even if such a definition extends itself to a freak flag. They aren’t proud members of a country, political party, or a coalition of freaks. They’re just Tony, and any attempt we make to define them as anything but –based upon the things they do and say– will say more about us and our need for definition, than it does them. Freak Flag Flyers tend to be moral relativists who ascribe to some libertarian principles when those political policies adhere to principles they find pleasing –those that suggest as Dave Mason did, “There ain’t no good guys, there ain’t no bad guys. There’s only you and me and we just disagree”- but they tend to distance themselves from the economic libertarian ideals, for that might result in too much libertarianism.

Some Freak Flag Flyers raise their flags in political milieus, but most freak flags involve simple eccentricities and peculiarities. An individual who prefers to listen to complicated and obscure music could be said to fly a freak flag in that regard, but they usually keep that information close to their vest when their more normal family members and friends are around. An individual who enjoys various concoctions of food, philosophies, and other assorted, entertainment mediums could be said to have a freak flag, but most of these people live otherwise normal lives. Every person can have a freak flag without being a freak, in other words, but the general term freak flag is reserved for those activities we engage in and those preferences we have that could be embarrassing if they found their way back to our normal friends and family members.

Even if we don’t have what others might call a Freak Flag, we can identify with the mindset of those who dared to let theirs fly. Now that we’re all normal and stable, we might not remember the days when we strove for some sort of definition, or we may be embarrassed by it, but most of us can recall a day when we dared to be different.

A friend of mine worked in a corporation, and he was a corporate joe from head to ankle. To maintain some level of freak flag status, however, he wore a wide variety of loud socks and skater shoes that were so out of place with the rest of his attire that it was impossible not to notice. If he was going to take a corporate gig, and become everything his boss needed him to be, he wanted to have something he could point to, to suggest he wasn’t a corporate sellout. We all have some sort of freak flag that we stand behind to separate us from the rest of the pack. Some of us are just a little more diligent in our efforts.

Thus, the ultimate definition of a freak flag flyer is a relative concept defined by the individual. It’s almost the opposite of my aunt’s attempts to be younger and hipper than her peers, as the true freak flag flyer does not engage in freak flag flying, they just are in a manner that is more organic than anything someone like my aunt might dream up.