Robert Ellis Orrall

400 Greatest Singles of the Nineties: #250-#226

July 23, 2010 // 22 Comments

A lot of songs from both ends of the charts here, including a husband-and-wife duet that spent six weeks at #1.

400 Greatest Singles of the Nineties: #250-#226

#250
I Meant Every Word He Said
Ricky Van Shelton
1990 | Peak: #2

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At least the third song on this list about a guy mulling over romantic gestures he wishes he’d made to his former love, and the most traditional among those songs. You could easily imagine this one being a minor classic by a 60’s or 70’s legend, so close is its replication of that style. – Dan Milliken

#249
I’m So Happy I Can’t Stop Crying
Toby Keith with Sting
1997 | Peak: #2

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My hard-and-fast rule for Toby Keith: The sadder he is, the happier the listening experience tends to be. He’s all kinds of sad in this snapshot of post-divorce melancholia, reflecting on everything from unfair custody protocol to the greater motions of the universe. Even a gratuitous Sting cameo can’t detract from the single’s gloomy grandeur. – DM

#248
You Ain’t Much Fun
Toby Keith
1995 | Peak: #2

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Toby Keith is also funny, though. What’s a man to do? Sobering up ain’t all that it’s cracked up to be from is perspective. Ever since he’s done so, his wife has been taking advantage of his increased functionality by giving him honey-do lists that he wasn’t ably tackling pre-sobriety. It’s enough to drive a man to drink. – Leeann Ward