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
iTunes stats: 319 plays
Previous ranking: #32
The legendary producer and gangsta rap pioneer, who suffered a stroke in 2021, sees 77 new listens while dropping three spots on the charts.
#34: Van Halen
iTunes stats: 328 plays
Previous ranking: #33
Fifteen tracks from the multiple incarnations of the band, which lost guitarist and founder Eddie Van Halen to cancer in 2020, drops one spot despite 93 new listens.
#33: Metallica
iTunes stats: 329 plays
Previous ranking: #30
The one-time masters of metal drop three spots in the rankings while picking up 66 new listens.
#32: Florence + The Machine
iTunes stats: 355 plays
Previous ranking: #35
The six-time Grammy nominees parlayed 132 new listens into a three-spot jump.
#31: No Doubt
iTunes stats: 356 plays
Previous ranking: #31
Thanks to 94 new listens, the ska band I saw back in college just before they hit it big stays even in the rankings.