12 Saddest Songs Ever? A Countdown . . .

The Yahoo! Music Blog recently featured a list of the 20 Most Heartbreaking Songs of All Time! It's a pretty good, sniffle-worthy list, featuring such sob song experts as The Everly Brothers, Billie Holiday, Kate and Anna McGarrigle, Roy Orbison, and George Jones. Since I like nothing better than a throbbingly sad song (so much more spiritually uplifting than a sappy happy song), I tried to come up with my own list, limiting it to a dozen (in a nod to the 12 days of Christmas, with sad songs replacing true love gifts and candle lighting), to songs with decent videos on YouTube, and to artists who already have a place in my iPod shuffle.

Without further ado, Saddest Song #12:

If self-love is the greatest love of all, then self-pity must be the greatest pity of all, and no one does that better than Morrissey and The Smiths. "Last Night I Dreamt That Somebody Loved Me" is one of my Smith favorites, the ultimate ode to anyone who's felt thoroughly unloved at some point, which must include just about everyone. The story is old, I know, but it goes on . . .

Saddest Song #11: 

Before they were cool again, the Carpenters were a joke, but, when I was a child and playing their records over and over, I wasn't in on the joke. When I was about 11, I wrote a play about juvenile delinquents which my friend, Carol, and I performed in my basement. "Bless the Beasts and Children" was my theatrical soundtrack choice. Everyone now knows that beneath the Carpenters' squeaky clean facade and soft pop arrangements deep sadness lurked, but, at age 11, I was unaware of Karen's personal struggles. I was an irony-free, first-time-around listener. Her voice spoke directly to by budding melancholic self. Without the tabloidy tragedy of Karen's death, would the Carpenters have been cool enough to warrant a 90s tribute album? Maybe not. But songs like "Superstar"--their most exquisitely sad and timeless single--are freestanding. So never mind that Karen's skirt looks like a shower curtain in this performance. Move past the kitsch to hear the voice. It won't be matched. (Although this cover of "Superstar" by Sonic Youth certainly has its gloomy merits.)

Saddest Song #10:

Jeff Buckley, the beautiful young man with the beautifully unique voice, silenced too soon. It's a Leonard Cohen song, covered by many, but Jeff will always own "Hallelujah." This version is rough around the edges, naked, unmistakably poignant.

Saddest Song # 9:

Though written to commemorate those killed on 9/11, "If This Is Goodbye" is subtle enough to be a universal meditation on loss and the simple power of love even when the meaning of life seems most fragile and unknown. Performed by Mark Knopfler and Emmylou Harris, two mature artists who know a few things about understatement, with Mark's haunting guitar playing, the song, which appeared on their duet album All the Roadrunning, sends a fresh shiver of recognition down my spine each time I hear it.

Saddest Song # 8:

Bruce Springsteen is a master at capturing the lost dreams of youth, the human mistakes and life realities that can kill hope even as his narrators look romantically back at their glory days, days that vanished before there was time to realize that those brief, careless joys of youth were as good as it was going to get. "The River" is probably my favorite Springsteen song, and this live reinterpretation is even more sadly haunting than the studio version from the 1980 album.

Saddest Song # 7:

In the spirit of holiday shopping during tough economic times, a 2-for-1 Special for Saddest Song # 7. Nina Simone and Tammy Wynette aren't obvious musical soul mates, but these two songs--"If You Knew" and "'Til I Can Make It On My Own"--ache with need and love in a similar way, and both artists strip them down to their essence. They both knew a thing or two about heartbreak, and it shows in their guileless performances.

Saddest Song # 6:

Lucinda Williams's "World Without Tears": never has the word "if" been used more powerfully or poignantly.

Saddest Song # 5:

Janis Ian's At Seventeen was a naked tribute to everyone who's ever felt like an ugly duckling outcast in high school, and apparently that was a lot of us, since the 1975 song was a huge hit and still resonates today. Ian became an unlikely star in the 60s, at age 15, with her song about interracial romance, "Society's Child." (Think of Britney Spears, then think of her opposite, that's Janis Ian as a teen performer.) I was a devoted fan of Ian's melancholy, often minor-key 70s albums. Though I knew nothing of romantic love at the time, I assumed it would be as gloriously gloomy as her songs. Then, I grew up, she fell off my radar screen, and her additional hits didn't materialize. I was reintroduced to Ian in the 90s when she became an essayist for the gay (aha!) magazine, "The Advocate"--her funny, outspoken columns about life with "Mr. Lesbian" were nothing like the somber Ian I imagined from her music, but that was appropriate since I'd also come out and was no longer the isolated teen seeking musical angst in which to wallow. But, after hearing her in a solo concert in a Burlington, Vermont chapel a few years ago, I reconnected to the music, too, and remembered what first drew me to it. "Jesse," her plea for a lover's return is simple, spare, and timelessly haunting. It was my favorite song of the night, and the video reminds me why.

Saddest Song # 4:

It took a while for George Michael to get respect as a pop artist. Wham! hits like Wake Me Up Before You Go-Go didn't inspire one to think much beyond, "Remind me not to wear short-shorts," and, "That's the gayest dancing I've ever seen." I loathed Wham! with a passion and therefore was reluctant to listen to any George Michael songs even after Wham! was kaput. I heard a few things I liked on his solo albums "Faith" and "Listen Without Prejudice," yet I still wasn't ready to fully listen without prejudice until "Jesus to a Child" from "Older." I remember first hearing it on the car radio and being floored by its tender beauty. "Older" was an appropriate title for the album--Michael hadn't been heard from in a few years (record company legal problems partly responsible for the silence), and the album showed a new, subdued maturity far removed from Wham! short-shorts go-go-ing. Though Michael had yet to publicly come out (that would take a bathroom bust a few years later), I read it as his coming out. Songs on the album clearly speak to a (male) lover's death, and I found them incredibly moving. The album wasn't a huge critical or popular success in the US, but it should have been. In recent years, Michael has gotten more attention for his personal traumas than for his music, but songs like "Jesus to a Child" and "You Have Been Loved" are a reminder of what a great, emotionally sensitive artist he can be.

Saddest Song # 3:

With Billie Holiday it's not so much the individual song but what she brings to it. She doesn't have to sell a song. She seems to live inside it. Her performances of "Fine and Mellow" and "Strange Fruit" are both so extraordinary--and extraordinarily different--I couldn't pick between them. She delivers the ultimately sad lyrics of "Fine and Mellow" with an almost casual acceptance--love could work out and he might treat me right, but it probably won't and he probably won't--making them all the more poignant. Her obvious joy in playing with other jazz greats almost turns this into a happy blues. "Strange Fruit," on the other hand, is simply devastating. As Billie says, "I don't know, the blues is sort of a mixed up thing, you just have to feel it. Everything I do sing it's part of my life."

Saddest Song # 2:

I'm a fan of Antony and the Johnsons gorgeously fragile album, "I Am a Bird Now," but I thought it was a little far-fetched when a friend told me he'd seen Antony in concert and wasn't the only one weeping in the audience. Antony's unique voice is an acquired taste, but it's quavering vulnerability perfectly suits the songs. Seeing Antony perform combines that vulnerability with the strength that comes from laying out emotions with complete focus and intensity. Antony's riveting performance of Leonard Cohen's If It Be Your Will is one of the highlights of the "I'm Your Man" documentary. And watching Antony at the piano singing "Hope There's Someone" makes me understand the tears. Physically, he doesn't much resemble Billie Holiday, but I sense a spiritual connection in the way they're both able to find the raw beauty inside a song and radiate it outward.

Saddest Song # 1:

If I had to pick one song I know I'll never tire of listening to, it would be this one, "Goodbye," written by Steve Earle. I first heard it on Emmylou's brilliant "Wrecking Ball" album. This version has both Steve and Emmylou. Add regret, broken romance, lost years, a soft breeze and Novembers. Stir. For me it doesn't get sadder better than this.

Goodbye to the 12 Days of Sad Songs.

My Flickr friend, Tim Connor, has come up with some very worthy suggestions for my Saddest Song list. Check them out on his blog. (He was also kind enough to reference my photography work in the same post; Thanks, Tim!) Tim's an excellent photographer and writer on photography, so I encourage anyone to regularly visit his Flickr photostream and his Looking at Photography blog, where you'll find his photography-related insights along with some terrific links.

I'm sure I left some worthy triple-hanky musical tearjerkers off my list, so feel free to post suggestions in the comments section.