"I'm Living Up to Her Low Expectations" (1995)
Singletary's first single, and first hit, made the right impression by setting the bar low — thematically speaking, at any rate. Written by Bob McDill and Tommy Rocco, "I'm Living Up to Her Low Expectations" dropped a month before his self-titled debut LP, cracking the country Top 40 as it reached Number 39 in the spring of 1995. From the fluttering opening guitar lick to Singletary's stone-cold twang, it was built on rock-solid honky-tonking fundamentals. But its real charm came from the lyrics' carefree self-sabotage, a self-fulfilling prophecy of disappointments assuaged by the boozing and buddies that got him in trouble in the first place. J.G.