Leonard Cohen - Suzanne
Cohen, of course, has more perfect songs than your average songwriting legend. Hallelujah, Famous Blue Raincoat, Bird on a Wire, or No Way to Say Goodbye could just as easily have made it on this list. Suzanne, though, is my personal favorite. It tells a story of such depth, detail and honesty (at least in the emotional sense), that I think of Suzanne as an estranged, eclectic, tragic aunt, who my family has tried and failed to keep secret.
Paul Simon - Still Crazy After All These Years
This song deliciously and succinctly captures nostalgia, which is not a simple feeling to capture. There is sweetness, elation, longing, and a healthy dose of regret, all seamlessly set to one of the prettiest and most memorable melodies I know. I've told this story before and I'll tell it again: Paul Simon is quoted in "Songwriters on Songwriting" (Zollo) describing the writing of this song. He says he was stepping into the shower when the refrain came to him, and "... I wasn't very happy about it, either. I didn't say 'Oh, that's a good one, that's clever, I can use that.' It was an assessment of where I was at the time, and I wasn't very happy that that was my assessment." I think Paul's feeling of vulnerability and reluctant honesty comes straight through those speakers, and that's part of the magic of this song.
Joni Mitchell - A Case of You
Joni has lots of perfect songs also, Chelsea Morning and Both Sides Now being close contenders for this list. This song, though, is quickly becoming a standard, and for good reason. Among other things, I love the ambiguity; it's ambiguous without being at all confusing. We hear the love and devotion, along with the conflict in the relationship, and what's worse: the conflict of a flighty artist's heart. It's a true and perfect story.
George & Ira Gershwin - Our Love is Here to Stay
Singer/songwriter Peter Mulvey once told me a beautiful story about this song. The Gershwins were not a married couple but brothers, George wrote the music and Ira wrote the lyrics (to dozens of gorgeous jazz songs and musicals, including 'They Can't Take That Away From Me', 'Someone to Watch Over Me', 'Porgy and Bess', and many more). George, Ira's baby brother, died at the age of 40, leaving a final composition behind. That composition was this song, to which Ira penned the lyrics, "It's very clear... our love is here to stay. Not for a year, forever and a day".
Bob Dylan - You're Gonna Make Me Lonesome
What strikes me first about this song, every time, is its sweetness. Who knew Bob could be such a sweetheart? What strikes me next is the simplicity: lines like "when something is not right, it's wrong". Then, the chorus hits, and my heart lifts, too. And again with the simplicity, and the doggone truthiness of it: "I could stay with you forever, and never realize the time".
Patty Griffin - Peter Pan
Patty is one of my personal favorites. The emotional intimacy in her voice, and in her lyrics, is so complete, and so effortless, I feel like I know her feelings better than my own. This song is a gem among gems - how perfectly, and touchingly, she describes the sad inevitability of growing up.
Steve Earle - Tom Ames' Prayer
This is a perfect story song. "Lily, Rosemary and the Jack of Hearts" can eat the shorts of this song. Rocky Raccoon wishes he were half as cool as Tom Ames. "He cocked both his pistols, and he spit in the dirt, and he walked out into the street." DAMN!