People always ask me what makes someone a "real" crooner. Like there's some secret handshake or you need to own a certain number of bow ties.
The truth? I think most people have it backwards. They think crooning is about having this perfect, smooth voice. But I've heard plenty of technically perfect singers who left me completely cold.
What actually matters is something way simpler and way harder: you have to mean what you're singing.
When Bing Crosby started crooning in the 1930s, he wasn't trying to fill a concert hall. He was talking directly into this new invention called a microphone, having a conversation with whoever was listening. That intimacy - that's the whole thing.
I learned this the hard way during my early performances. I was so focused on hitting every note perfectly that I forgot to actually connect with the songs. It wasn't until I started thinking of each song as a story I was telling a friend that things clicked.
Now when I sing "Dream a Little Dream of Me," I'm not performing it - I'm sharing it. There's a difference, and audiences can feel it immediately.
The funny thing is, some of my best performances have been when my voice wasn't at 100%. Maybe I had a slight cold or was tired, but I was more emotionally present. Those are the nights people remember.
So if you're thinking about trying to sing these old songs, forget about sounding like Sinatra. Focus on meaning what you're saying. The rest will follow.
What's a song that you can't help but sing with complete honesty? I bet it's not because of the technical difficulty...