Some songs, such as "Pretty Boy Floyd" or "Greenland Fisheries" or "Folsom Prison Blues" or "Banks Of the Ohio," I can sing and be pretty confident that no one will think the song represents my own experience, beliefs, or views.
Others, such as "Okie From Muskogee," I sing pretty much snarkily or sarcastically (as do most of the people who sing along with me).

But there are other songs that reflect views that are antithetical to mine and which I think singing them might be taken as an endorsement, so I don't sing them. (This includes pretty much anything written by Hank Williams Junior.)