Is it possible for me to sing at the right pitch instead of using pitch correction?

OK, without using any type of pitch correction software, is it really possible for me to sing at a pitch that would match the music being played? Since I can re-do it over and over until it sounds right; is this a good approach or should I just use pitch correction software from the get go? And by the way, changing my own pitch manually with my own voice, is that an unnatural thing to do? Instead, should I change the pitch of the music to match the pitch that I'm accustomed to singing?

Depends on the genre.

A modern pop song, no.

Any other song, possibly.

A pop song these days will sometimes have fantastic singers, sometimes terrible singers. They will do 10+ takes for maybe the verse, and more for the chorus. Chorus will be layered like crazy. There will be a hell of comping going on. Often you might even get one individual word made up of three separate takes, perfectly blended to sound like one perfect note (it's not actually that hard to do, I do it all the time, but it depends on what you have to work with as to it's realism). After all that, they often tighten things further. Even if it already sounds perfect. Subtly this can still sound natural, but a bit naturally over perfect. Most go overboard and someone with a little audio experience can hear it. You can't sing like that. It's digital.

Most other music (as far as I've heard) is either pitch corrected naturally as needed, or not at all. A great singer will just do a few takes, a little comping and it's perfect. A not so great singer will do loads and loads of takes, crazy comping, then pitch correct to taste.

In reality, if you're not a fantastic singer, you'll need to pitch correct (if you want it all perfect). I do typically 6-10 takes of a song, then any trouble sports, I'll loop the recording and smash out another 10 or more takes of that section. This can take an hour. You try singing one song for an hour. It's tiring. You'll also find over time you start to sing differently (unless you're amazing, I'm not). This often means you can't realistically comp the earlier takes with the later takes. It's amazing how you can think it sounds exactly the same, but SO different. Additionally, assuming you're perfect in that regard, you sometimes find you sing one word with great emotion and sound and delivery, but it's a little out of key. EVERY single other take of that word is in key, but doesn't have that same emotion that is vital for the song. You are tired. You can't sing with any emotion any more. You're warmed down. Try recording another day maybe? You'll find the next day you sound completely different. It just doesn't blend. Sounds like a different person. This is when it is now time to use pitch correction. I get this all the time. You know you can sing the part. You just didn't get it in the take. Spend another hour next week re-recording the whole thing, or suck it up and use the tools Cakewalk gave you. Alternatively, get singing lessons and practice, practice practice!

These are my experiences from being a crazy comper. I'll comp everything for the perfect take. I'm not a great singer so this is what I find I need personally. You results may differ. At the end of the day though, you don't have $$$ clicking on the clock, so choose what you will.

Enjoy.

And check out some vids on comping. Plenty of ways to streamline the process, which is important!

Interesting question.  But what I really want to know is is it possible for me to change my mood for the better on a rainy day or should I just change the weather and make the sun shine?

Great post Doug