“Some of the times you just gotta let your Freak Flag fly,” my aunt said to her brother. I had no idea what they were talking about, and I didn’t really care, but I didn’t think any definition of this otherwise illusory idiom could remedy my dad’s issues. If Freak Flag is actually a thing and not something my aunt just made up, I thought, my dad may have been as far from having a Freak Flag as anyone on Earth. His primary goal in life was to fit in, and he did anything and everything he could to make that happen. My aunt was the opposite. She did everything she could to stand out as a hip, cutting edge, and appear young, or her definitions of all of the above. She knew more about the hip artists and songs in Billboard Top 40 than I ever have, she wore hip, cutting edge clothing better suited to women ten years younger than her, and she dropped whatever hip terms she heard young people say. When she dropped the term Freak Flag I thought it was yet another one of her embarrassing attempts to appear hip, but that particular phrase stuck with me for whatever reason. 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.

“Dude, I don’t know. I’ve been saying it for decades,” he said. Unbeknownst to me, this was the key to keeping it cool in the phraseology universe, for no one ever seems to know where they hear hip, cutting edge terminology 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 appeared 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 user just started using the phrase last February, those who are evasive and defensive want us to think they’ve been saying it for so long that they dismiss all questions about its origins as uncool.

If we found a truly reflective individual who didn’t mind talking about the first time they heard the phrase, it might result in a humdrum response, “My Cousin Ralphie is da shiznit, and when I heard bra 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, 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 in the hip, phraseology universe is that we better hurry up and use the terms we enjoy saying as often as we can before a kool kat 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 is so 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 kool kats step in to warn us that it’s over, it’s a serious blow in this artificial architecture, and we 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 never encountered some kool kat who declared your favorite phrase 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 kool kat 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’s 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, kool kat 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 his words of advice on dating. 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 unveil 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 the doofus was more attractive and a little less chubby, I may have been more amenable to his guidance on the matter.

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For fact checkers, a decent search on “Let your Freak Flag fly” suggests that it 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. Due to the fact that these first appearances occurred in an artistic venue, however, we can guess that the phrase made its way through the “in-crowd” circuit long before Hendrix or Crosby used it in their songs.  

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 they, the Freak Flag Flyers know, we would be just as sophisticated in our skepticism about allegiances.

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 eagerly provide this information to anyone who asks. 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 allegiance or definition … 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 Tony –based on what 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 principles adhere to matters they find pleasing –those who 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 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 the 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. We 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 once 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 Freak Flag Flying friend of mine, a Dan, worked in a Fortune 500 corporation, and he was a corporate joe from head to upper calf. To maintain some semblance of his Freak Flag status, however, Dan wore a wide variety of loud socks and skater shoes that appeared out of place with the rest of his business casual attire that it was impossible not to notice. I’m not sure if it enhanced Dan’s Freak Flag flyer status or took away from it, but he did have flames of fire on those Converse Chuck Taylors, and he wore these notoriously short-lived Chuck Taylors for about a decade, so he must’ve purchased them on an annual basis to keep his preferred characterization alive.

When I asked Dan why he wore that ensemble, he said, “I just like it” in the typical “I’m just Tony” Freak Flag Flyer vein. I dug deeper, of course, and I saw a man who wanted to succeed in the corporate climate by being everything his boss wanting him to be while not being a complete corporate sellout. He wanted the best of both worlds, and he thought some flames on his feet allowed him to let Freak Flag fly.

I’ve met the “I’m just Tony” Freak Flag Flyers who can’t articulate their need to fly one, and they attempt to nullify any questions about their nature by asking you why you think they’re different. Some think we’re putting them on trial, and we are, sometimes. Sometimes, we’re just interested in their essence. I’ve met others who were just different people, and they were quite comfortable draping themselves in a Freak Flag. They taught me that the ultimate definition of a Freak Flag flyer is a relative concept defined by the individual. It’s almost the complete 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 who they are in a manner that is more organic than any character my aunt might dream up.