Sing what you want and what you like and what you enjoy. You will have to hear it a lot of times learning it and singing it, mabe eaven for years, if it is the right song. BUT remember the three tenants are, tone, timing and material.

Tone - Not every one can sound like Frank Sinatra, Dean Martin, Nic Jones, Kate Rusby, Dick Gaughan or Iris DeMent. So dont't try. Be yourself.

Timing - Not every one can have the timing of...the above list. But they are worth a good hearing. They all have special, timing. Try working on your timing.

Material - Not everyone can have ..... well actualy you can have great material, pinch, steal, borrow, approprate, take it over, make it up, get it anywhere you can. But make it yours. Be yourself. And have fun. Geting lost in a big ballad or a silly song is great. Comunicating that song to an audence of ten( or 100 and 10 or 2 )is fabulous and adictuive.