3. Ease Down the Road (2001)

Is that a guitar solo? A guitar solo on a Will Oldham album? And I don’t mean a wail of anguished skronk but a real slab of Steely Dan wonkery. When this noodling surfaces on the first track, “May It Always Be,” it announces a side of Oldham we haven’t seen before. And it’s not just the crisp production courtesy of indie rock journeyman David Pajo that shocks. Here, Oldham embraces the no-bullshit storytelling approach of his alt-country peers like Wilco and Whiskeytown.

Following the dark, timeless poetry of I See a Darkness, Ease Down The Road is a bit of a come-down. But in the context of late 90s/early 00s alternative country, it’s one of the best albums that era had to offer. The bouncy road-trip of a title track finds warmth, beauty, and humor in marital infidelity (only “a little guilt, and some guilt spilt”). And “After I Made Love To You,” a personal favorite of Oldham, is as sweet and honest a love song as you’re likely to hear anywhere.