One of the truly nifty features of Apple’s iTunes software is that it maintains a count of how many times a song is played. Whether you play the song while at your computer or on your iPod while on-the-go, iTunes is remembering what you like the most - and least - about your collection. Since I’m an early-adopter of technology, I’ve been listening to almost all of my music in this manner for about 6 or 7 years. During that time, iTunes has been keeping track of my favorites.

Today I thought I’d take a look at what Sinatra music I’ve listened to the most, on a song-by-song and album basis. I whittled the list down to the Top 25  and the results were somewhat surprising. For starters, half the list was consumed by songs from Christmas Songs By Sinatra and A Jolly Christmas From Frank Sinatra, both of which get heavy play during the holiday season. But keeping them on the list didn’t seem fair because I don’t generally listen to them at other times of the year. So I factored holiday songs out of the equation and ended up with the 25 Sinatra tunes I’m most likely to listen to throughout the year.

Of the twenty-five songs, nine Sinatra albums are represented:

• Come Dance With Me
• Come Fly With Me
• Only The Lonely
• Songs For Swingin’ Lovers
• A Swingin’ Affair
• This is Frank Sinatra
• Sinatra: Vegas (Disc 1) (See my review of this amazing collection)
• Where Are You? (A whopping 9 songs are on the list.)
• The Rat Pack at The Sands

It was no surprise to me that most of the material was from Sinatra’s Capitol period. What did surprise me was how many songs from Where Are You? made the cut - more than half the CD is represented in the list.

Shown below is the list in its entirety. Subjectively, I might have picked a somewhat different list of songs; but these numbers don’t lie: these are the twenty-five Sinatra songs I’ve played most often in recent years, including the albums on which they appear.

1. From This Moment On    from A Swinging Affair
2. Brazil    from Come Fly With Me
3. Lonely Town    from Where Are You?
4. Where Are You?    from Where Are You?
5. The Night We Called It A Day    from Where Are You?
6. Autumn Leaves    from Where Are You?
7. Something’s Gotta Give    from Come Dance With Me!
8. Dancing In The Dark    from Come Dance With Me!
9. I Cover The Waterfront    from Where Are You?
10. Day In-Day Out    from Come Dance With Me!
11. Angel Eyes    from Only the Lonely
12. Oh! Look At Me Now    from A Swinging Affair
13. Maybe You’ll Be There    from Where Are You?
14. Laura    from Where Are You?
15. I Only Have Eyes For You    from The Rat Pack at The Sands
16. Come Fly With Me    from Come Fly With Me
17. Only the Lonely    from Only the Lonely
18. You Make Me Feel So Young    from Songs For Swingin’ Lovers
19. Got You Under My Skin    from Songs For Swingin’ Lovers
20. Imagination    from Sinatra:Vegas (Disc 1)
21. The One I Love Belongs To Somebody Else    from Sinatra:Vegas (Disc 1)
22. I’m A Fool To Want You    from Where Are You?
23. Baby, Won’t You Please Come Home    from Where Are You?
24. I Love Paris    from Come Fly With Me
25. If You Are But A Dream    from This Is Frank Sinatra 1953-1957 (Disc 2)

Want to see your own list? If you run iTunes it’s very easy. Click on ‘View’ and ‘View Options’; make sure ‘Play Count’ is checked. Then, go the the search box in iTunes, type ‘Sinatra’ and click on the ‘Play Count’ column in the resulting list to sort by most -or least - listened to.