4 years ago, we last counted down the Top 200 songs in my iTunes library. Since my iTunes stats are still intact, across multiple PCs, iPods, iPads, and iPhones, I figured it was time to take another look at my most listened to songs, based on number of plays as of January 1, 2020.

Today, we enter the top 5, where we will go more in depth into each song.  The fifth most listened to song in my library, with 168 plays since my stats began in late 2007, is a traditional favorite and a live performance from the late 1970s.

#5: Harry Caray – Take Me Out To The Ballgame
iTunes stats: 168 plays, most recently on 11/20/2019
Previous ranking: #10

Harry Caray joined the White Sox broadcast booth in 1971, becoming popular with the South Side faithful and enjoying a reputation for joviality and public carousing.  Returning owner Bill Veeck, knowing that Caray would sing along to Take Me Out To The Ballgame in the broadcast booth during the Seventh Inning Stretch, wanted Caray to lead the crowd in stadium-wide event.  Early in the 1976 season, Veeck secretly installed a public address microphone into the broadcast booth and turned it on once organist Nancy Faust started playing the song.  Caray initially did not want to do it, but, as Veeck explained, “Anybody in the ballpark hearing you sing Take Me Out to the Ball Game knows that he can sing as well as you can. Probably better than you can. So he or she sings along. Hell, if you had a good singing voice, you’d intimidate them, and nobody would join in.”  Caray finally agreed to sing it live, accompanied by Faust on the organ, and went on to become famous for singing the tune.

This version features Caray and Faust and comes from a YouTube video compilation of Caray’s performances from the late 1970s.  While Caray left the White Sox following the 1981 season and passed away in 1998, I still include the song on my White Sox victory playlists, attributing to its high play total.