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”
Good variety covering the monster hits and some of the lesser known ones too! On a personal note, one of the first CDs that I can remember hearing my mom play was A Horse Called Music which featured “Nothing I Can Do About It Now.”
Another hopeless task you’ve set for yourself Kevin – I could select any of another 25 songs and have it be just as essential so I won’t quibble with your excellent list except to say that you should have included one of Willie’s recordings from the early sixties such as “Crazy” and/or “Night Life”.
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