Here’s a comment my brother made and it’s just too good to have it hidden in a comments section:
I remember seeing the Dean Martin roasts and being scared, like a drunk friend of an drunk uncle had showed up unannounced at a dinner party and started shoe-horning everyone into singing along to perverted folk songs. I didn’t know what he was famous for and those roasts seemed to hint that he didn’t really know why either.
then, years later as a grownup, I heard “Ain’t ThatA Kick In the Head” in some movie, or in a bar. That’s really all you need to do…just listen to that song a few times in a row. It all seems like a joke. Then you start to hear how well he sings the song. Then you realize that someone could have completely fouled the song up. It isn’t a very good song, actually. Think about all the classic standards. Everybody does ’em. But is there another famous version of that song? If there is, I haven’t heard it.
How does he turn a mediocre song around? He doesn’t sound all that invested in the heartbreak aspect of it, there isn’t irony dripping all over the place. I still can’t quite place what makes the song work so well. But I’m going to try,..
His presence and personality are so evident that you don’t even need the song. He has sung the song out of existence. All you want to do is hear him make a rumble in his throat and roll his eyes about how much trouble a broad can be. You also somehow realize that no broad ever caused him too much trouble. He causes them trouble. And they love it.
It is almost a taunt. What could be a stupid jokey brush off of heartache turns into a come on. It is a magic trick.
Another thing that strikes me about Dean Martin is that you get the sense that he would have behaved EXACTLY the same had he been a truck driver, a grocer, a whatever. Most of the other stars of that era seem to have been transformed in some way by fame and what came along with it. This guy could have strolled around the streets of Rome with his jacket over his shoulder and 10 bucks in his pocket and it would make NO DIFFERENCE TO HIM.
The most underrated of all time.


YES! Especially that last sentence.
The iTunes Store has several versions of “Ain’t That A Kick In The Head”, and they drive your brother’s point home with great force. They’re awful: Brian Evans, Deana Martin, Frank Lamphere, John Pizzarelli, The O-Tones, and Veronica Martell.