I’ve only recently discovered the Most Played feature on iTunes, since it never had any relevance until iPods were large enough in memory to sync all of my music. So going back to early 2011, I have a lengthy list of the songs I’ve played the most.
Johnny Cash may have been too dark for country radio back in 1994, but his morbid single lives on alongside debut singles, seventies covers, and a whole lot of Mary Chapin Carpenter.
400 Greatest Singles of the Nineties: #125-#101
1999 | Peak: #1
Sure, the melody of the chorus sounds just like “It Matters to Me.” But “Breathe” took the country power ballad to new heights, becoming Hill’s signature hit in the process. – Kevin Coyne
Life’s a Dance
John Michael Montgomery
1992 | Peak: #4
It’s the catchy fiddle riff that’s so memorable about John Michael Montgomery’s debut, number one, single. He is known for being a balladeer, but this one is an up-tempo motivational song. – Leeann Ward
Proving that the airplay charts don’t tell all of the story, this part of the countdown features several singles by nineties stars that didn’t reach the top but have stood the test of time.
400 Greatest Singles of the Nineties: #175-#151
I Wish I Could Have Been There
1994 | Peak: #4
This is the country equivalent to “Cats in the Cradle”, but more tender and less selfish. – Leeann Ward
Sometimes She Forgets
1995 | Peak: #7
Tritt gives a surprisingly but fittingly subdued performance on this cover of a Steve Earle song, telling the story of a woman who sometimes forgets that she’s sworn off men. I can never get enough of the incredibly cool arrangement. – Tara Seetharam
The first quarter of the countdown comes to a close, highlighted by excellent comeback attempts by T. Graham Brown, Emmylou Harris, and Willie Nelson.
400 Greatest Singles of the Nineties: #325-#301
He Would Be Sixteen
1992 | Peak: #31
Sometimes the choices that you make linger forever. Here, a woman in her thirties drives past a high school football game, and her mind wanders to the painful void left in her heart from the son she gave up for adoption. – Kevin Coyne
It Matters to Me
1995 | Peak: #1
Faith Hill’s sophomore album is a surprisingly deep set, filled with candid insights into different womens’ lives. The title track represents that spirit well, as a woman articulates the differences in her and her man’s relationship approaches with impressive precision. – Dan Milliken