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 wrap up the first half of the list today with our next batch of ten artists, crossing over from play totals of two digits into three and featuring the highest charting debut.
#110: Chance the Rapper
iTunes stats: 99 plays
Previous ranking: #89
The two clips from the Chicago born rapper’s intro video for the 2016 White Sox gained only six new plays over the last five years.
#109: Pink
iTunes stats: 100 plays
Previous ranking: #107
The three-time Grammy winner added 22 additional listens to the four songs that are in my collection.
#108: The Strokes
iTunes stats: 102 plays
Previous ranking: #110
The alternative band from New York rises two spots on the list thanks to 29 new listens to four songs off their debut album, not including a mash-up with Christina Aguilera.
#107: The Outfield
iTunes stats: 103 plays
Previous ranking: #85
With their only song in my collection being the walkup music for former White Sox infielder Gordon Beckham, the group from London’s East End added a mere four plays over these past five years.
#106: Blues Brothers
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