In addition to the main interpretation here, I think there’s another related meaning that’s intended. Bobby may have told her that he was freeing her, and she’s saying that this freedom he gave her is bullshit. “Nothing, that’s all that Bobby left me,” she says: having everything taken away is an empty kind of freedom.
As such, it’s not fatuously dismissing poverty or tyranny.
Daniel
How I wish she had grown old and could be interviewed about the lyrics by Terry Gross on Fresh Air. 
I always thought it had meaning on several levels, one being that “freedom isn’t all it’s cracked up to be-- it’s just another way of saying you have nothing left to lose.” IOW, you’d don’t have anything. No posessions to tie you down, but no one to count on, either.
Tom Petty sang, more recently, that “When you got nothin’, you got nothin’ to lose.” I think that’s one of the meanings of the line we’re talking about. That can be freeing, but it’s also lonely.
That was Bob Dylan and it was in the same era.
I think my favorite line was
Sometimes the independence you imagine isn’t truly as great as the interdependence you have.
Ah, right you are. Dylan also said it, and Petty referenced it in “Climb that Hill” about a decade ago.
I know what song you are quoting, but I have, by maintaining a very careful regimen throughout my entire life, so far managed to avoid hearing it.
I’ve just realised: - Richard Thompson’s song ‘Beeswing’ is 'Me and Bobby Magee’ re-written but from Bobby’s point of view…
And I said that we might settle down
Get a few acres dug
Fire burning in the hearth
And babies on the rug
She said O man, you foolish man
It surely sounds like hell
You might be lord of half the world
You’ll not own me as well…etc
Mods, please chastise if I am resurrecting a thread that is too old…
But what does this part mean:
I pulled my harpoon out of my dirty red bandana
I’s playin’ soft while Bobby sang the blues, yeah
What is a harpoon? (apart from a whale thing)
Purely from context (it’s small enough to fit in a bandana; you can play it and it sounds like harpoon), I’d guess ‘harmonica’.
That’s what I’ve always thought it meant as well.
And Petty did pen the conceptually-related lyric:
And I’m free – free fallin’
I always liked the play on words involved-- This line versus the first line in the verse.
The first line (“freedom = nothing left to lose”):
means that being free isn’t the most important thing in the world.
In the exciting atmosphere of newfound freedom during the hippy 60’s, that was an unusual statement. Being free was the ultimate goal, to defy the conformity of your parents and the 1950’s . Wear jeans and a long hair, not penny loafers and brylcream. Posters proclaiming “do your own thing”, " free love" were ,like, man, really deep.
Very few young people then would dare to say that freedom ain’t so great.
The second line (“nothing aint worth nothin’ , but its free”) is a great double entendre.
It reminds you that, in your freedom, you only have a whole lot of nothing. But, you can still try to convince yourself that you’ve got something–'cause you’ve got your freedom. Sour grapes!–sure, you’re lonely and lost without a girlfriend or boyfriend to love. But you can still love your freedom–for whatever it’s worth
(sorry for over-analyzing, and sounding like an unemployed grad student. But, man, those lyrics meant a lot to me back then. Nostalgia just ain’t what it used to be…)
Good lord, lighten up. This is pop music we’re talking about here.
I think the words ring very true. As having lost parents and a spouse, the pain from the voids created by the losses outweighs any increase in freedom from any obligations from the relationships.
Since this has been revised, and I missed it the first time…
You have to remember it was written in a time when hippies roamed the earth. It’s written from the perspective of one of those free spirits. These innocent souls thought they could go on like that forever.
People could be free from responsibility and yet could still eat and hitchhike. Look at Lobo’s “Me and You and Dog Named Boo”. Look at The Girl in Two Lane Blacktop.
I wonder what happened to the singer character (“me”) as she got older. I hope she didn’t die young. It’s been a long, long time.
Go at it from the other direction. Assume someone values freedom – from tyrannical bosses, from obligations that cramp their style, from having to conform to the expectations of the neighbors, everything. They don’t compromise.
There are price tags. People won’t hire them, don’t treat them like “normal folk”, don’t include them, dont’ trust them because they aren’t playing by the rules.
Fast forward a bit, let’s say a couple years, and you find the uncompromising freedom worshiper hitchhiking, unemployed, no home, owns only what’s in their bag or on their back. They’re still free though.
A wry commentary on the price of freedom.
The flip side of the 2006 coin is the beginning of Pippin’s finally song (words by Stephen Schwartz)
I’m not a river or a giant bird
That soars to the sea
And if I’m never tied to anything
I’ll never be free
I wanted magic shows and miracles
Mirages to touch
I wanted such a little thing from life
I wanted so much
I never came close, my love
We never came near
It never was there
I think it was here
And the flip side that if you are truly free, then you don’t have anything either. That’s always how I interpreted it; that having nothing left to lose was essentially negative, and that saying that you’re free, means that you’re also truly unattached/unengaged. Basically what AHunter3 says… (read it after my post).