Going old-school.
This song is older than Tony Bennett himself.
The old standards from the “great American songbook” provide me with a bit of a dilemma. Whose version do I go with? It should be a version I’ve heard and enjoyed, but often there are several. I’m sure I first heard and enjoyed this classic when Harry Connick, Jr. put his spin on it for 1989′s “When Harry Met Sally” (one of my favorite films.) I probably would’ve gone with that version, but I knew Tony Bennett had this song in his repertoire, and I decided I preferred his more old-school rendering to Connick’s big-band arrangement.
Now, there are recordings by Billie Holliday and Frank Sinatra and, apparently, John Travolta, among what are likely hundreds. Wikipedia lists a couple dozen. Spotify has about five dozen versions. Tony Bennett alone probably has recorded a half-dozen or a dozen versions. I’ve heard a bunch, from every stage of his career. In 2011 for his Duets II album, he sings it with Carrie Underwood. I was going to go with Tony Bennett’s 1994 performance for MTV Unplugged, since that’s the Tony Bennett version I’m most familiar with. However, I decided I should go back to when Tony first recorded it, and that would back in 1957, though he never released it as a single. Since I can’t find a recording from 1957, I’ve grabbed one from 1964. Close enough.
When I give the year of a song, I’m going with the year of the recording I’ve chosen. When every song was initially written is beyond the scope I’m willing to go, for now, except when it’s a classic such as this, and I’m curious about its origins.
“It Had To Be You” dates back to 1924, and you can read more about it in Wikipedia, since I don’t do much digging beyond that.
Here’s Tony Bennett from 1994:
And:
Tony Bennett | 2011
And here’s Harry Connick, Jr. from 1989:
359Tony BennettRags To Riches
366Tony BennettIt Had To Be You

So are you saying there are not multiple cover versions of any song in this countdown? I would have rated the Harry Connick version higher than Tony Bennett.
Right, there will not be multiple cover version of any song. It just gets too complicated. Say there’s a song I really like, and I really like 20 different covers of it. I can’t very well have 20 versions of the same song in the countdown. Maybe that’s not such a great hypothetical.
More easily put, I just wanted to go with one artist’s rendering of a given song. Sometimes, like in this case, it was a tough decision. And I actually considered whether there were a bunch of good covers of a song when rating a song. Usually, there’s an original recording of a song, and then lots of subsequent covers. In this case, there’s not an original recording, and nothing especially noteworthy for a few decades.
I might like the Harry Connick version better on some days. I had a note in my files that said “TB > HC” so I went with that.