Good question. I'm not sure there really is a "freak flag" because everyone is expressing something that they have gotten from someone else or a group, so most individuals flying their "freak flag" is just another follower or hanger on. Rebellion is a long time part of being a teenager, so most teenagers that rebel are not necessarily flying their freak falg but just doing what comes naturally ....... rebelling against authority.

Wasn't the phrase in the song, "Almost Cut My Hair", written by David Crosby ? My take on it was that he was expressing a sort of melancholia, and seems to be speaking from the mid to late winter season, some time after Christmas (when he had the flu and 'wasn't feeling up to par'). I don't remember thinking that it had much to do with either of the Kennedy brothers' assassinations, though that could lead one to feeling melancholic if one wallowed in those thoughts long enough. I don't remember that being mentioned in the song though, even metaphorically.

Perhaps CS&N song was “Long Time Gone”? Backstory see link.

https://americansongwriter.com/behind-the-song-lyrics-long-time-gone-by-crosby-stills-and-nash/

Yep, 'Long Time Gone' was written by Crosby the night Bobby Kennedy was killed after Crosby heard the news. It does mention getting one's hair cut in the context of... if you want to try to get yourself elected you'll probably have to cut your hair so you can more easily run with that crowd of people that you'll need to run with to become an establishment figure.
When I saw 'freak flag' earlier, though, my mind just went immediately to 'Almost Cut My Hair'.

The best song by the best band that you've never heard of    Freak Flag Here Come the Mummies!

Teenage rebellion is a necessary ingredient for “leaving the nest”,,, chafing against authority’s rules. I vamoosed after high school to escape a stifling religious upbringing… forever thereafter I felt I was being chased by the hounds of hell….

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Originally posted by chuckv97

Teenage rebellion is a necessary ingredient for “leaving the nest”,,, chafing against authority’s rules. I vamoosed after high school to escape a stifling religious upbringing… forever thereafter I felt I was being chased by the hounds of hell….

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Many years ago I studied and presented to spirituality group of wondering souls the Thompson poem, "Hound of Heaven."  I needed interpretation of Victorian Age language and idioms to even begin to understand his message.  Brad

I rebelled internally at the time. The pent up anger that only increased throughout my teen years darn near killed me. I did not want to disappoint my dad who suffered near death injuries as an 18 year old Marine on a battleship. At one point when I was 16 I moved out and lived with a friend’s family for a while. Eventually mom convinced me to come home after a few months. I finished high school and went away to college. Dad and I had had a good relationship in time. Brad

..... mucho gray area, blurry lines, "whaddya mean by ______ ?" IMNSHumbleO.

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Originally posted by banjo bill-e

The best song by the best band that you've never heard of    Freak Flag Here Come the Mummies!

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That are pretty darn good!

I suppose the the most I let my FFF was when I bought a used motor cycle in college and put a peace sticker on it. Wasn’t I a rebel. ;-). 1972 was a mess for. I returned to college in Wichita after doctors would not let me play football anymore. So I got married instead. That year Viet Nam vets were pouring into college. I was dealing many issues, but nothing like my new friends with PTSD and other readjustment issues. Somehow we all managed to deal with our own personal troubles and get through college. It was surely interesting and trying times, for sure. Everyone flew their freak flag for their own reasons and experiences. Then most of graduated, got “professional” jobs and assimilated. And life went on . Brad

I'm pretty sure that buying one's first banjo is a freak flag flying moment of the first order.

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Originally posted by reubenstump

I'm pretty sure that buying one's first banjo is a freak flag flying moment of the first order.

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I think you are correct.

Ahh, yes! The teenage urge to be "different".
Back in the '70's that meant the boys had to have long hair, tie-dyed tee shirts, and bell bottom pants, just like millions of other boys.

My pal Steve used to show up at meetings of Students for a Democratic Society with long hair, a white shirt, and a necktie. He enjoyed watching people try to figure out which pigeonhole they should put him in.

Nowadays, seems that all one has to do to be "different", is to NOT get a tattoo.

I dunno.  This one seems a bit different...

Owen, good one!

“ What's the difference being different / When it's difference now that looks alike?” is a lyric from John Hartford's 1968 song “Natural to Be Gone”.

When I hear the term FFF, I immediately think of Archie Bunker and Meathead (Michael) having a conversation!!!
Slammer!!!

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Originally posted by slammer

When I hear the term FFF, I immediately think of Archie Bunker and Meathead (Michael) having a conversation!!!
Slammer!!!

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https://youtu.be/CrmLGsv77Ko?si=B0Xs36I0ztWmxFnU

I got out of high school with no prospects and a low draft number. I joined the Navy and for four years and three months did as I was told. I got discharged, started college, and shortly after got hired on the city police department. I worked full time and went to college part time for eight years and two promotions. By the time I got to a point I could let my freak flag fly, I was retired and people just thought I was a crazy old man. So no, I never had an opportunity to rebel.

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Originally posted by BG Banjo

I got out of high school with no prospects and a low draft number. I joined the Navy and for four years and three months did as I was told. I got discharged, started college, and shortly after got hired on the city police department. I worked full time and went to college part time for eight years and two promotions. By the time I got to a point I could let my freak flag fly, I was retired and people just thought I was a crazy old man. So no, I never had an opportunity to rebel.

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But thank you for your service!  Brad

I’m a queer, banjo playing, poly, tatted up punk rock dude, my freak flag has been flying a long time but I really hit my prime in my 40s.

Life is short, live it to the hilt! That said, life is about doing what brings you joy. So it’s entirely reasonable not to have a freak flag to fly.

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Originally posted by South Jersey Mike

I’m a queer, banjo playing, poly, tatted up punk rock dude, my freak flag has been flying a long time but I really hit my prime in my 40s.

Life is short, live it to the hilt! That said, life is about doing what brings you joy. So it’s entirely reasonable not to have a freak flag to fly.

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Mike, Now that you say that, perhaps I finally did let my freak flag fly in the first decade of the 2000s. That is when I came out and publicly admitted I played banjo.  Brad

... probably qualifies as an old banjo joke (?):  "Banjo players are proof that we live in a free country." [... or something like that.]

I looked straight as an arrow until I graduated college in Montreal and got a job. But I'd been avidly collecting LPs for years and the music helped turn me 'round. Plus, university helped with critical thinking. At my job, one of the guys asked what I'd do if management asked me to get my (not that long) hair cut. I said I'd tell management to go to hell. When my art director said the president wanted me to get my hair cut I said no. His response was a shocked, "So, you meant what you said." The hair wasn't the issue (I was in a band by that time), but other things were, and I quit. I moved to Toronto and took up teaching. My parents came for the Grey Cup game. When Mom saw me, her first words were, "Paul! Your hair!" It was never that long, but I saw it as some sort of identification, or separation from a type of life I didn't want. Dad was in big business and I wasn't built that way.

While "Almost Cut my Hair" had the "freak flag" line, quoting Hendrix, David Amram wrote a song that stated, "Remember, when you grease your hair, Nixon greased his, too." I always took that line to heart.

I recall when a couple of classrooms were going to be made into one room for the library (small K-6 school). So, as we were preparing to move classrooms, I would show up in jeans, t-shirt, and sandals. The principal, Steve, called me on it and I said no big deal, I'll change. I think he expected blow back from me and said that if I felt strongly about it I should lay my job on the line. I said it wasn't an issue and we went back and forth for over a half-hour. He just wanted to filibuster me 'cause he didn't get the argument he expected. He must have still been miffed 'cause, earlier, he'd said staff would decide which floor the library would go on, but he made the decision, and I called him on it at a staff meeting. A bunch of us were told to change classrooms and teachers were convinced that I wouldn't, but fair is fair and I moved. (Steve was actually a great guy and later I transferred schools to work for him again.)

I guess I had a reputation for speaking out 'cause, at a staff meeting, the teacher beside me said that, "We should do (whatever she was thinking - I can't recall) ... Tell them, Paul!" I said nothing. Not my idea!