Since he's one of the few country legends who is best defined by his albums rather than his individual tracks, creating a Starter Kit for Willie Nelson is a tough row to hoe.
What follows is the cream of the crop from Willie Nelson's peak years, minus the collaborations with other artists. His pairings with other great acts would be another Starter Kit unto itself.
When you're ready to dig deeper, check out his studio albums in their entirety, starting with Phases and Stages and Shotgun Willie, moving on to Red Headed Stranger and Stardust, and picking up lesser-known classics from the later years, like Spirit, Teatro, and You Don't Know Me: The Songs of Cindy Walker.
“Yesterday's Wine” from the 1971 album Yesterday's Wine
Nelson encounters an old friend at a local drinking establishment and they share a round of drinks as they reflect on how they're “aging with time, like yesterday's wine.”
“Whiskey River” from the 1973 album Shotgun Willie
It's since become a live favorite of Nelson's fans at a speedier tempo, but there's a a beautiful melancholy to the studio version found on this album.
“Bloody Mary Morning” from the 1974 album Phases and Stages
A centerpiece of what is arguably Nelson's finest concept album, it's since become something of a standard. Also of note from this set is “It's Not Supposed to Be That Way.”
“Blue Eyes Crying in the Rain” from the 1975 album Red Headed Stranger
A most unexpected breakthrough hit came in the form of an old country classic delivered with sparse accompaniment.
“The Troublemaker” from the 1976 album The Troublemaker
It just might be the best country song ever written about Jesus. It's certainly more grounded in the Gospel than anything I've heard in mainstream country music.
“Georgia on My Mind”
>from the 1978 album Stardust
Trying to pick the best cover from this collection of pop standards is difficult, but this is probably his best vocal performance on the collection.
“My Heroes Have Always Been Cowboys” from the 1980 album The Electric Horseman
A flawless deconstruction of the American cowboy archetype.
“On the Road Again” from the 1980 album Honeysuckle Rose
Nelson's ode to the road has livened up countless road trips over the past three decades, making the miles fly by for two minutes and change.
“Always on My Mind” from the 1982 album Always on My Mind
Nelson's stroke of genius was delivering this oft-recorded song as an anniversary pledge to be a better husband rather than as the postmortem of a failed relationship.
“City of New Orleans” from the 1984 album City of New Orleans
Who better to sing Steve Goodman's celebration of southern America as seen from a boxcar?