Music speaks to all of us in a very unique way. Your favourite performer can make you feel a special connection, make you feel like you’re friends. And they certainly seem like friends sometimes: they seem to be there at all the right moments, exactly when you need them. And sometimes it’s not even a specific artist. Sometimes the right song will hit you in the right way at the right time. Remember the scene in “Jerry Maguire” when Jerry was on a high having had a successful meeting? Driving away, he began scanning the radio for just the right song to fit his mood, one he could sing along to at the top of his lungs. (He eventually found it: Tom Petty’s “Free Fallin'”). Stumbling on the right song fresh out of work on a sunny Friday afternoon can be a golden moment.

But what of the other side of the coin? Equally poignant can be the ‘sad songs’. There can be times in your life when you’re going through a break-up and you keep going back to the same songs that seem to fit your situation. They can even act like friends that help you hold things together. Maybe the singer sounds like he’s been there, too. That can really help. And then there’s the REALLY sad songs that you sometimes feel the need to just immerse yourself in even though you know they’re just making it worse.

Which brings to mind Frank Sinatra’s ‘torch’ albums. In the early days of the LP, FS pioneered the ‘concept album’: an album full of songs with a common theme. He had his upbeat, swingin’ albums and he had his ‘torch’ albums: songs of sadness, loneliness and despair. Nobody ‘inhabited’ a song like Sinatra. He was truly an actor when he sang, playing a role. Having ‘been there’, he recorded songs of heartbreak like no one else. The album’s titles say it all: “In the Wee Small Hours”, “Where Are You?”, “No One Cares”. Frank’s son famously remarked that his dad’s album “Only the Lonely” should be sold by prescription only. Later, Sinatra recorded the album “Watertown” which was comprised of a cycle of songs depicting the dissolution of a marriage. Gut-wrenching stuff. I say today that I wish I had had these albums back in the day. Although, it’s probably a good thing I didn’t.

It seems to me that a song can be not necessarily sad but wistful. I can think of “Sunday Will Never Be the Same” by Spanky and Our Gang. The lyrics recall a relationship that used to feature walks through the park on a Sunday afternoon. But now, it’s over. It’s not exactly heartbreaking but it’s sad to remember the relationship and the way things used to be: “Now I wake up Sunday morning / Walk across the way to find / Nobody waiting for me / Sunday’s just another day”. Another ‘sub-genre’ would be the nostalgic sad song. The melancholy, bittersweet remembrance of an era in life. I’m thinking of “The Old Crowd” by Lesley Gore: “I still think about those good times we knew / We were so carefree then, our hearts were on a cloud / how I miss the old crowd”.

Then you have the ridiculous. The too-obvious ones, the maudlin songs. One of the very first popular singers, the legendary Al Jolson, had a hit with “Sonny Boy”. Legend has it that songwriters jokingly wrote this for Jolson because of his penchant for tear-jerkers. Al had the last laugh – the song spent 12 weeks at #1 in 1928. In the lyrics, Sonny Boy – only three years old – dies at the end. Which brings us to what they actually called ‘death rock’. In the Golden Era (1954-1963), songs that portrayed people dying was a thing. These, of course, are too obvious to be really sad. Depressing is a better word. “Teen Angel” by Mark Dinning – car hit by train (“just sweet sixteen and now you’re gone / they’ve taken you away”). “Last Kiss” by J. Frank Wilson and the Cavaliers – also car accident (“something warm running in my eye”). The Everly Brothers’ “Ebony Eyes” – plane crash (“I knew the heavenly ebony skies / Had taken my life’s most wonderful prize”). Then, years later, “Honey” by Bobby Hebb. This song is truly fascinating because despite scaling the heights of schmaltz it became what I call a ‘contemporary classic’ or a modern-day standard: everybody and their mother recorded a version. In this tune, this poor slob is lamenting the loss of his lovely, young wife (“the angels came”). Breaking up is hard to do but do we need songs about wives and fiancées dying?

Let’s get down to the best of the sad songs. Songs that are so well done and hit the mark so perfectly in lyric and in composition that they are actually a joy to hear:

“What’ll I Do?” – written by the legendary Irving Berlin, this tune, rendered properly, is absolutely heartbreaking. It was effectively used over the opening credits of the 1974 film version of “The Great Gatsby”. Nelson Riddle won an Oscar for this film’s score which used this song as a theme. Most of the great singers in history have recorded this song. “When I’m alone with only dreams of you that won’t come true, what’ll I do?”

“All Summer Long” by the Beach Boys. I always say this is the saddest song I ever heard. This is the last song I listen to every summer, before I go to bed Labour Day night. Definitely falls in the nostalgia category we talked about earlier. The lyrics speak of all the fun and freedom young people enjoy during the summer. “We’ve been having fun all summer long”. This tune is much more poignant due to George Lucas using it over the closing credits of his landmark film “American Graffiti”. The film is a depiction of the definite end of an era of history. Summer ending is appropriately symbolic of not only a moment in time but also the end of our youth. Our coming of age.

“Brown-Eyed Girl” by Van Morrison. Here’s a paradox. What song sounds more joyous while bombing down the highway on the first warm day of spring? But it occurred to me several years ago that the lyrics are very sad. Here is a nostalgic look back at the past, at things that happened before and don’t happen anymore. “Do you remember when…”. I’d love to hear somebody do a slow version of it. Van sounds like a man who has had to somehow move on and is struggling with it. And that’s sad. So many times we get caught up in recalling a failed relationship or a past lover that we can’t move forward. Consider: “So hard to find my way now that I’m all on my own…cast my memory back there, Lord, sometimes I’m overcome…”.

“My Whole World Ended (the Moment You Left Me)” by David Ruffin. Here is a great example of everything coming together. The lyrics, yes, sad. But here we have, unlike “Brown-Eyed Girl”, a composition that seems to reflect the sadness. I’m not a music scholar but I hear LONGING in the chord changes. But the crowning aspect is the voice of David Ruffin. The lead singer of the Temptations during their first hit-making years, David recorded this as a solo outing. Anguish. There is absolute anguish in his voice. You can hear it in every note he hits particularly when he sings the title and “now my body is numb…”. I have to say, I’ve been in pretty good shape romantically for sometime now but I have actually wept listening to this song. Shivers.

“Separate Ways” by Elvis Presley. Art imitates life. Elvis Presley had separated from his wife, Priscilla, one month and four days prior to recording this in 1972. Putting emotion into a song was one of the many things Presley did well and, all things considered, it wouldn’t have been too difficult to sing this like he meant it. Co-written by Red West, the words are just really sad: “There’s nothing left to do but go our separate ways and pick up all the pieces left behind us / and maybe someday, somewhere along the way, another love will find us”. Again, the music is sad here, too. Especially the piano at the end. Longing for something lost.

“It Makes No Difference” by the Band. Bassist Rick Danko takes the lead here and his tenor voice almost comes across as a whine. Again, anguish. “And the sun don’t shine anymore / and the rains fall down on my door…and I’ve never felt so alone before”.

“Bobby Jean” by Bruce Springsteen. Springsteen understood Spector. It’s always been said that the production of the landmark album “Born to Run” borrowed from Spector’s grand style. I can hear that style here in the chord changes of this song from “Born in the U.S.A”. I always come back to the word ‘longing’ – there is real longing in this track even without the vocals. The lyrics are sad, too: guy goes looking for an old flame. Her mother tells him she’s gone. Think Jenny from “Forrest Gump”. Sweet girl goes out into the world, searching, selling herself short all the while. Our boy is the only one who gets her. He’s perfect for her but she doesn’t know it: “Maybe you’ll be out there on that road somewhere / and you’ll hear me singin’ this song / I’m just callin’ one last time NOT TO CHANGE YOUR MIND BUT JUST TO SAY ‘I MISS YOU, BABY’ / good luck good bye Bobby Jean”. Just then Clarence Clemons delivers some of the saddest sax you ever heard.

“Wish It Were Me” by the Platters. Tony Williams, lead singer of the Platters, is the unsung hero of all ’50’s singers. His voice had a quality that transcended simple pop singing. Emotional delivery on these lines: “Yes, I pray that my prayers
will touch you, touch you for true / so you’d love me too / and the whole world would see”. Here’s a man who feels like nothing unless he has her by his side: “and the whole world would see”.

“For the Good Times” – Ray Price’s original version. It’s a toss-up between this song and “All Summer Long” for the saddest song I ever heard. Maybe this is flat-out sadder because where “All Summer Long”‘s sadness comes more from a feeling of nostalgia, “For the Good Times” speaks of a man who’s descended into the pathetic: I don’t care if you don’t need me or love me, I can’t survive without you so pity me. Just stay here with me and I’ll pretend. “Make believe you love me one more time”. If the chorus is sung well – and you’ll find lots of good versions of this song – it is the saddest five lines you’ll ever hear. It’s even raining.

You can’t wallow in sadness. But if you have to visit there, take these tunes along. They’ve been there.