When someone talks so much about a topic that it's getting annoying and you think they're getting paid for it but in the end you're getting into it yourself.
#1 Did <Name> tell you about <Topic>?
#2 <Name> is talking about nothing else, they're such a campain, I even bought some for myself.
Sleeping outside in the backcountry without an overhead shelter (such as a tent or tarp), usually done in the context of backpacking. The decision to cowboy camp is a calculated one - bugs, rain, snow, etc. are all possible backfires to the decision and can damper the experience.
Note that having an adequate shelter is a must, cowboy camping is the decision to forgo setting up a dedicated shelter and betting that conditions will be such that the shelter is not needed (but the dedicated shelter is still present/available should it be needed). Not bringing adequate shelter with you into the backcountry is foolish and can result in injury or death.
Roof Camping is a term used to describe pussies in games such as Rust, where highly geared players far into the game sit on top of their base shooting people enlarging their ego for the 1 out of every 50 bullets they hit.