Music. It is a powerful thing that brings people together, creates memories, and evokes emotions. It is the universal language that speaks to the soul. It forms the soundtrack of our lives.
It has now been five years since we last counted down the Top 200 artists in my iTunes library, featuring the songs I have listened to the most since 2007. It is time to do so again, seeing which performers still resonate and if any newer ones have joined the fray. So, without further ado, here are my most listened to artists, based on number of plays as of January 1, 2026.
We hit the top 40 today with the next batch of ten artists, much of which is tied in some way, shape, or form to one of the local baseball clubs.
#40: Tori Amos
iTunes stats: 263 plays
Previous ranking: #43
66 new listens for the same eleven songs over the past five years push the singer/songwriter, who I was supposed to see live at the Rosemont Horizon back in 1998 but missed due to a friend’s wedding, up three spots.
#39: The Rolling Stones
iTunes stats: 289 plays
Previous ranking: #37
The 1989 inductees into the Rock and Roll Hall of Fame added 76 additional listens, which dropped them two spots in the rankings.
#38: Steam
iTunes stats: 296 plays
Previous ranking: #36
A casualty of my White Sox victory playlist getting fewer plays over the last couple of years, Steam drops two spots in the rankings despite 76 additional plays.
#37: Harry Caray
iTunes stats: 300 plays
Previous ranking: #40
Two versions of Take Me Out to the Ballgame, one from his tenure in the White Sox booth and one from the Cubs, scored a 44% increase for the legendary broadcaster.
#36: Captain Stubby and the Buccaneers
iTunes stats: 308 plays
Previous ranking: #34
The novelty band, responsible for the White Sox rally song from 1959, added 79 listens in the past five years, causing them to drop two spots in the rankings.
#35: Dr. Dre
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With Purdue’s loss to Arizona in the Elite Eight, my brackets, and my remaining interest in this tournament, are officially toast.




Maybe it is personal bias, but I am expecting big things from the two Big Ten teams in this bracket, including one making their way to the Final Four.
Purdue followed up a disappointing end to the regular season with a spirited run through the Big Ten Tournament to capture the championship. Are they fixed? Well, I hope so since I have them coming out of this region and heading to Indy. 