There are a lot of ways to interpret Kris Kristofferson's lyric "freedom is just another word for nothing left to lose." I've always seen it as the more optimistic cousin to Dostoyevsky's "if God is dead then all is permitted", since both are implying that unlimited choice is simultaneously a gift and a curse, but Kristofferson seems to be emphasizing the gift more while Dostoyevsky seems to be emphasizing the curse more. After all, Kristofferson is equating being possessionless with being unburdened - a power-of-positive-thinking type of person could easily take him to mean "there's no limit to what you can do once you open yourself up to risk". In contrast, the most obvious interpretation of Dostoyevsky's saying is "we can never allow ourselves to believe that the are no limits, because if we do we will descend into chaos."
You could see either interpretation in Schizopolis, Steven Soderbergh's most existentially challenging movie. The film holds up all of the cornerstones of modern life and then ridicules them, and it's up to the viewer to decide if Soderbergh's subversions are as funny as he thinks they are or if they are really just nihilism in disguise. (Honestly, it's probably a bit of both - after all, darkness and comedy are not mutually exclusive.)
Schizopolis starts up with a very domestic scene: a husband (played by Soderbergh in his only acting role to date) arrives home and is met at the door by his wife (who is played by Betsy Brantley, who was actually married to Soderbergh at the time.) The twist is that the two of them don't actually have a conversation - they have a meta-conversation, where Soderbergh-as-Mr. Munson says "Generic greeting!" and Brantley-as-Mrs. Munson says "Generic greeting returned!" The implication is that the specific words they are saying don't matter at all because they could all be swapped out for blunt statements of intent and they would be just as communicative. Schizopolis presents these characters in the most reductive possible manner as a way of suggesting that most human interactions can be boiled down to a pre-scripted formula that we will repeat over and over again without ever realizing that we're stuck in a loop.
The rest of the movie follows a similarly absurd pattern: Mrs. Munson tell Mr. Munson that she is going to go see a movie when she is, in fact, going to have a tryst with her lover, a dentist named Dr. Korchak - who is also played by Soderbergh, but this time in glasses. Korchak is trying to get Mrs. Munson to leave her husband, but as soon as she commits to leaving the first version of Soderbergh for the other version of Soderbergh things fall apart, because Korchak has changed his mind - he no longer wants to marry Mrs. Munson now that he's met "Attractive Woman #2" - who is also played by Brantley. These characters treat every act of love and betrayal as if they were incredibly important, but the audience is well aware that the whole thing is a farce - these people are going to end up with the exact same partner regardless of what choice they make because all of their available options are interchangeable. (They are so interchangeable, in fact, that at some point the characters stop getting names - they start to be identified by a descriptor and a number.)
Schizopolis' view of work is even more grim and meta than it's view of romance. Mr. Munson is an office drone who is ordered to write a speech for a phony self-help guru (who is semi-blatantly modeled on L. Ron Hubbard.) He procrastinates on the assignment, then he lies to his boss over and over again about how much progress he's made, and when he isn't not-working and lying about not-working he's selling his company's worthless secrets to a rival company for shits and giggles. His absolute antipathy towards his soul crushing job makes sense, because his whole job is about swindling people into believing in a bogus cause that no one should believe in (but the people who do buy into it seem to get much happier overnight.) Eventually Munson does figure out how to take all of his bosses contradictory demands and turn them into a speech that everyone is happy with - and of course what he's written is nothing but a pastiche of catchphrases that sound good together without actually saying anything.
But that doesn't even matter because the guru is violently interrupted mid-speech by another character, a gonzo exterminator named Elmo Oxygen. Elmo is pure id - all he does is talk in nonsense phrases ("Nose army. Beef diaper?"), seduce housewives and assault other characters. (Halfway through the movie he beats up an extra as a way of announcing that he's quitting the production; the next time we see him he agrees to continue filming but only if the producers will convince an attractive P.A. to sleep with him.) Elmo is the only character who seems to have any existential satisfaction in the whole movie - and that's only because he acts exactly like an animal would. You could take one quick glance at the liberated and happy Elmo and the repressed and bitter Mr. Munson and conclude that human nature is inherently awful and that civilization is probably doomed.
However, it's worth remembering that Schizopolis is (on the surface at least) a comedy - when Munson/Korchak/Soderbergh says "I can't believe I'm cheating on my wife with my wife" he's pointing out the silliness of the film's plot, not making an argument about how free will is all an illusion. The film also treats Elmo Oxygen as a particularly dark joke, since the character is mostly a sight gag - he's a scrawny balding man who is constantly babbling dada-ish drivel and yet the ladies all find him irresistible. Most of these characters are not laughing at their lives the same way the audience is, but they do have enough self awareness to realize that their lives are some kind of sick cosmic joke.
Steven Soderbergh made this film at a very specific time in his life: he was getting divorced from Brantley and his career was in the toilet because every film he had made in the wake of sex, lies and videotape had been less successful than the one before it. He was a point where he had to unburden himself of all his own insecurities or else they were going to ruin his life. Schizopolis seems to have done the trick; he followed this up with Out of Sight, which was a completely mainstream movie where beautiful Hollywood stars romanced each other when they aren't committing/stopping crimes. Which is why I've always seen this movie to be more on the "freedom is just another word for nothing left to lose" side and not the "if God is dead then everything is permitted" side - if you watch this in the context of his overall career you can see how this purely-an-art-film indulgence liberated him to such a large degree that he could turn around and make a very commercial film without feeling like a sell-out. Of course, you could also see it the other way - that Schozopolis was his attempt to kill God by making a movie that followed no rules and which was extremely pessimistic about the nature of existence, and that it has no positive outcomes at all. Or it could be that both are true at the same time - after all, it is named Schizopolis, so why wouldn't we expect it to have multiple semi-contradictory outlooks at the same time?