The 50 Best Songs Ever Written

Of course, what I mean is “In My Opinion – The 50 Best Songs.” But that would have made for an unwieldy title, and it’s understood anyway. Any list of “Bests” has to be subjective.

I want to issue a proviso that I really haven’t listened to a great deal of music in my lifetime. I’ve always driven older cars whose radios (if there were any) were unreliable, so I’ve traveled in silence, even on the longest road trips. At other times, I usually didn’t have any radio playing in the background.

As this list makes plain, a lot of the listening I have done centered around what has been considered “country” music. Before readers groan in dismissal (many people tend to sneer at country music), I want to specify that I listened to country music primarily through the 70’s and 80’s when the term “country” was often a catch-all term applied to songs that weren’t either quite folk or quite rock. So the designation included a lot of music that was distinguished simply by strong individual voices with distinctive timbres and by songs that told a story or painted a picture in ways that transcended any musical categories. I was introduced to Leonard Cohen’s music when he appeared on “Austin City Limits,” presumably a country venue.

Also, it’s often hard to say whether I’m choosing the singer or the song. In many cases, the two are indistinguishable. There is often a mystical union of the two under ideal circumstances, so that, as Emerson and others wrote, “I am the singer and the song.”

This list was admittedly built on shifting sands. If I were to have posted it yesterday, it would likely have been different. I’m continuously thinking of other songs that deserve inclusion, and I’m re-evaluating songs that were included, sometimes finding on a fifth or sixth listening, that they aren’t really that great after all. Sometime in the future, I might add a list of “Runners-Up” to this count-down, acknowledging all the songs that I remember too late.

Furthermore, the precise ordering of the songs, especially past the first ten or so, is rather arbitrary. There really was no way to say which song should be No. 38, while making another song No. 41.

Finally, I’m only considering popular songs that contain the traditional elements of lyrics, rhythm, and melody. So I haven’t considered songs from such genres as opera, hip-hop, or rap.

I include a little of the history of each song, or else some of my personal associations with it and the reasons I consider it to be one of the best.

So with a nod to Casey Kasem, here’s my Countdown of the 50 Best, working from the bottom up –

50. Happy Days Are Here Again, by Milton Ager and Jack Yellen, as sung by Annette Hanshaw/ as sung by Barbra Streisand

The reason I included this song and so many others on this list is because of their hidden complexity, their special potential for duality, for light and dark, cheer and tragedy. I return to credit this trait in the first song on my list. But “Happy Days” certainly has had that dual nature brilliantly revealed. On the one hand it has had singers such as Hanshaw who rendered it as the rousing, bouncy campaign song that propelled FDR and others to office. But then along came Streisand who found the almost unbearable cry of paradox and pathos inherent in the song.

49. Summertime, by George Gershwin, as sung by Ella Fitzgerald

This song steeps the listener in a summertime I really would never want to spread my wings and fly away from.

48. Broken Arrow by Robbie Robertson, as sung by Rod Stewart

This song was likely intended to refer to a Native-American’s love offering – not the fancy, store-bought thing that Europeans consider a suitable gift, but just the small, personal token that has some buried history attached to it. Because of this, some people have objected to Rod Stewart’s coopting the song. But I think Stewart’s touching voice carries the meaning. His accompanying video is also one of the most visually striking I’ve ever seen, although since it doesn’t have any reference to Native-American life, it might be a reason to object to its association with the song. However, whatever the song’s intentions, I find myself humming it, thinking of it often. As I’ve mentioned in other essays here, I have a number of friends who are hoarders and who take delight in the kinds of gifts others would spurn. As I trudge up to a friend’s door carrying some tattered, muddy artifact I found in the alley, I often catch myself quietly singing, “Who else is gonna bring you a broken arrow; who else is gonna bring you a bottle of rain.”

47. Is That All There Is?, by Jerry Leiber and Mike Stoller, as sung by Peggy Lee

With this song, I’ve already broken my rule about nominating only songs that have a continuous melodic line. This song is largely spoken narrative with no musical back-up. However, the chorus is sung and gives meaning and music to the whole. It also, sadly, too often reflects my reaction to life. As I stood in front of the Eiffel Tower, lit up at night, my companion’s eyes filled with tears. I, on the other hand, heard Peggy Lee’s let-down murmuring in my head. I wished I could have been my companion then, feeling her same intensity of response to the beauty.

46. Waltzing Matilda, lyrics by Banjo Patterson, as performed by the Australian Army Band/as sung by Noel Watson

The melody of this song is another one that is inherently bipolar. It can be a spirited march, or a sad refrain. It has the strange capacity to evoke longing, a sense of lost love waltzing off beyond one’s reach. And yet, that isn’t what the lyrics are about. In Aussie slang, “waltzing Matilda” just refers to walking around with your knapsack. I was shocked when I learned about this prosaic reality. It was as disillusioning as some children find the revelation that there is no Santa Claus. But the melody, filtered down from a variety of traditional sources, carries the day. The listener can perhaps choose to forget about the knapsack and return to picturing the beautiful Matilda in her swirling skirts, waltzing away into history.

45. Role Me on the Water, by Bonnie Koloc, as sung by Bonnie Koloc

This is the most sensuous song I ever heard, sung in that crystalline voice by the woman whom many describe as “the best singer no one has ever heard of.” Well, few people outside of Chicago’s “folk” scene have heard of Koloc, and perhaps she is just as happy about that. Perhaps she’d agree with Emily Dickinson when she wrote, “How dreary to be somebody, how public like a frog.”

44. The Gambler, by Don Schlitz, as sung by Kenny Rogers

Some people sort of laugh at this song as being too facile, too folksy a piece of wisdom. But it’s true - so much success in life depends on knowing when to stay and when to go, although a lot of that is luck. But to the extent it’s a reasoned knowing, I perennially seem to have lacked such an instinct. I have lurched from one private Viet Nam to another, always throwing the good after the bad, always staying too long in hopeless efforts. I have yet to learn when to “fold em” so that I might break-even in some day of final reckoning.

43. Looking for the Heart of Saturday Night, by Tom Waits, as sung by Tom Waits

This is one of the cases where the singer and the song are inseparable. It takes the marriage of music, lyrics, and Waits’ gravelly, gin-soaked voice to boost this song into the top 50.

42. Like a Rock, by Bob Seger, as sung by Bob Seger.

I first heard this song when it was used to advertise Chevy trucks on TV. Some people felt that Bob Seger sold out by lending his song to such commercial purposes. But I was grateful that corporate profits had led to my being introduced to this stirring backward look that a man takes to the years he was in his prime.

41. You’re the Top, by Cole Porter, as sung by Ethel Merman and Bing Crosby

It was almost a toss-up whether to include Cole Porter’s “Anything Goes” here, or whether to give precedence to this friendly tennis match of a song ripe for a duet in which compliments are lobbed and returned. “Anything Goes” has a unique chain-link sort of melody with interlocking phrasing, but its extended lyrics include too many references to scandals and jokes of the 1930’s that date the song. More of this song’s references stand the test of time.

40. The Wayward Wind, by Stanley Lebowsky and Herb Newman, as sung by Gogi Grant

This is the most onomatopoetic song I ever heard. When I was a child, I’d run into the room whenever this song came on the radio – to hear the wind blowing the drifter away from his border town.

39. Geronimo’s Cadillac, by Charles Quarto and Michael Murphey, as sung by Hoyt Axton

This song conveys the sharp edge of the cynical, cruel treatment that Native Americans often received at the hands of their white captors and of whites in general. In the early 1900’s, while Geronimo was being held as a prisoner of the U.S. Army at Fort Sill, Oklahoma, he would occasionally be trotted out for a “photo-op” in the hokey spirit of a Wild West Show. He never really got to own or drive a car. In an almost mocking spirit, he was just allowed to sit behind the wheel of one. Hoyt Axton, with his resonant growl, makes us feel the injustice of Native Americans being stripped of everything worthwhile in their cultures – while being given a meaningless “Cadillac” in return. (Antique car buffs say it wasn’t even a Cadillac that Geronimo is shown at the wheel of, but actually a less prestigious “Locomobile.”)

38. It’s a Wonderful World, by Bob Thiele and George Weiss, as sung by Louis Armstrong

This song makes you look around, feel, and appreciate.

37. Man on Fire, by Alex Ebert, as sung by Edward Sharpe and the Magnetic Zeros

Ebert irresistibly invites the whole damn world, “over heartache and rage… over panic and strange” – to “come dance with me.” The original accompanying video, filmed in New York at the Brownsville Recreation Center, is kinetic triumph.

36. Out Among the Stars, by Adam Mitchell, as sung by Joe Sun

This song tackles the unlikely topic of “suicide by police.” It’s particularly relevant now, with police shootings of “ghetto” youth having made headline news so often. It brings the listener into the pain and weariness on both ends of the gun when this happens. Many leading singers have covered this song, but the version done by Joe Sun, a great and under-appreciated country singer, is by far the best. As he represents the shame the boy’s father feels with that snarling catch in his voice - we can understand how the boy got to such a tragic point in his life. His parents are more concerned with what people think than with simply loving their child.

35. The Last Morning, by Shel Silverstein, as sung by Dr. Hook

Here on the heels of “Out Among the Stars” is another song about suicide – possibly. This mournful, despairingly evocative song was on the soundtrack of the wandering, surreal movie “Who is Harry Kellerman and Why Is He Saying Those Terrible Things About Me?” In addition to including this “best” song, the movie featured another best in the performance of Barbara Harris in a supporting role. The end of the movie presents the song’s meaning as being less equivocal.

34. A Couple More Years, by Shel Silverstein and Dennis Locorriere, as sung by Dr. Hook

When I first heard this song, with its refrain of, “I’ve got a couple more years on you babe, and that’s all. I’ve had more chances to fly and more places to fall” - I pictured having an older man sing the song to me. Now, several decades later, I have to picture myself singing the song to a younger man.

33. Let It Be, by Paul McCartney, as performed by The Beatles

Paul McCartney has generally been reluctant to pin down the meaning of this song. Is “Mother Mary” a reference to his own mother, or to the Virgin Mary? Either way, this is a beautiful encouragement to accept – the things we cannot change.

32. Glory Days, by Bruce Springsteen, as sung by Bruce Springsteen

Here’s a moving take on the barroom regrets of a couple of characters who peaked too early in life.

31. Take Me Home, Country Roads, by Bill Danoff, Taffy Nivert, and John Denver, as sung by John Denver

This was recently adopted as West Virginia’s official State Song, replacing earlier, less poignant evocations of the beauties of the State. Every time I hear the song, I want to get on the Greyhound bus and go back there where I’m lucky enough to have some acquaintances and always have a place to stay. One evening as I sat in my overalls on a rocking chair on my friends’ front porch and looked out at the rolling hills – I had to chuckle how I had become the perfect embodiment of the song’s “mountain mama.”

30. I’m So Lonesome, I Could Cry, by Hank Williams, as sung by Bernadette Peters

Elvis Presley said this song was “probably the saddest I’ve ever heard.” (Its authorship was contested by Paul Gilley.) Whoever wrote it, it is the quintessentially train whistle of mournful song.

29. Born to Run, by Bruce Springsteen, as sung by Bruce Springsteen

This song perfectly captures America’s infatuation with the natural mix of revving engines, sex, speed, and leaving. After I had worked 20 years at ushering my 1948 Chrysler through the restoration process, it was ready to hit the roads. A friend and I drove out to Lake Shore Drive on a Sunday dawn when there was little traffic in order to “see what she could do.” As we were picking up speed, a motorcycle gang, decked out in chains and all, pulled alongside us and signaled. The race was on. We accelerated to over 80 mph and beat the gang to the second off-ramp we passed. (Well, it’s possible the gang let the old car win.) But as we were speeding up, leading the pack, the same song automatically occurred to both my friend and me simultaneously. We both broke out with a rousing declaration of – “Tramps like us, baby we were born to run.”

28. I’m Always Chasing Rainbows, adapted by Harry Carroll and Joseph McCarthy, as sung by Judy Garland

Judy Garland could always be counted on to vocally paint the arc of a rainbow. This song makes art of the scientific fact that you can never touch a rainbow, no matter how far and fast you walk in its direction.

27. Auld Lang Syne, by Robert Burns with traditional folk melody, as sung by Rod Stewart

This song, with exquisite sentimentality, recalls the importance of honoring old friendships.

26. Brilliant Disguise, by Bruce Springsteen, as sung by Bruce Springsteen

This is a piercing reflection on the question of whether we ever really know the person we’re looking at. The song has a kind of twist ending as Springsteen turns the metaphoric mirror to face the other way. It’s also accompanied by one of the best music videos ever made.

25. The End of the Line, by George Harrison and The Traveling Wilburys, as sung by The Traveling Wilburys

If anyone you know is in despair and is considering ending it all, have them listen to this song. It’s almost sure to jounce them out of that mood.

24. All I Want Is You, by U2 and Bono, as sung by Bono

The haunting poetry and instrumentation of this song (“You say you’ll give me a river in a time of dragons… a highway with no one on it”) strips away all the non-essentials that clutter weddings and relationships in general, and leaves the listener with the simplicity of “When all I want is you.”

23. Ol’ Man River, by Jerome Kern and Oscar Hammerstein, as sung by Paul Robeson

A classic. This is a rare instance when two white men really seem to captured some appreciation for what black people went through. Ol’ Man River (the Mississippi) – “he don’t plant taters, he don’t plant cotton, but them that plants ‘em are soon forgotten.” We thank soldiers for their service; this song makes me realize how we should also thank all the nameless people for their toil through the centuries - creating all the goods of our lives.

22. When Johnny Comes Marching Home, lyrics by Patrick Gilmore set to Civil War tune, as performed by any marching band, as sung by Angel Snow

This song has an inherent undertone that contradicts the rousing cheer of its apparent theme. In this instance, the dual nature of the song likely wasn’t intentional since the melody has filtered down from a traditional Civil War-era folk tune. However, that tune was strangely composed and transmitted in what is likely an ancient form of the Dorian scale of music, different from our conventional modern major or minor scales. The song has different intervals than we are accustomed to hearing. That difference somehow automatically conveys a tone of sarcasm and derision of the cheering words that got attached to the song, resulting in what so easily can be heard as a moving anti-war protest.

21. Joan of Arc, by Leonard Cohen, as sung by Leonard Cohen

This song has imaginative lyrics that give a new, poignant meaning to being “consumed by fire.” Fire is personified as Joan’s groom as he declares he loves her because of her “solitude and pride.” That line alone is arresting because women almost never have been loved for such traits. It reminds me of the way Marlo Thomas shattered all conventional gender expectations when she opened her 1974 “Free to Be You and Me” TV special by reciting a fairytale about a Princess “beloved by everyone in the land because she was so – brave.” Rarely before or since has a woman been sincerely loved for anything but her “beauty” – until Leonard Cohen came out with these “Joan of Arc” lyrics.

20. He Played Real Good For Free, by Joni Mitchell, as sung by Joni Mitchell

This is a beautiful song which contains a beautiful encouragement to be alive in the moment and to appreciate what is all around us, even if it is presented “for free.” A famous violinist once sat out in front of Carnegie Hall where he was scheduled to play that evening at a charge of at least $100 a seat. The man played on the street corner a lot of the same music he was going to play inside in a few hours. Most pedestrians walked right by him, some actually registering disdain and dismissal of this presumably homeless man playing for his supper. A few tossed a coin or two his way. This song pays homage to all those people who play for free. May there be more of them, and more people awake to their contributions.

19. I Remember Loving You, by Utah Phillips, as sung by Fred Holstein

This touching song evokes the hardships of the 1930’s Depression, when only love could provide a person with a lasting, fond memory.

18. Bird on a Wire, by Leonard Cohen, as sung by Leonard Cohen

This is one of Cohen’s most famous songs. It contains the memorable line: “Like a bird on a wire, like a drunk in a midnight choir - I have tried, in my way, to be free.” As I’m writing this, it’s 20 degrees below zero in Chicago, but many of the homeless are still refusing to go to shelters, preferring to stay outside on the streets, free of the regulations and impositions and danger they often face in the shelters. They are illustrating Cohen’s famous observation about our most persistent attempts to be free.

17. What’ll I Do?, by Irving Berlin, as sung by Bernadette Peters

This is one of Irving Berlin’s most plaintive songs – a simple question, posed by a true musical genius.

16. He Went to Paris, by Jimmy Buffet, as sung by Waylon Jennings

A person would never guess this mild philosophical retrospective of a song had been written by Buffet, who is most known for his party-hearty booze bingeing songs. I don’t know if Buffet had the any particular man in mind when he wrote this, but it’s the biography of someone who drifted through life, frittering away his talent and time – something I can relate to only too well. But the listener is left with the feeling that perhaps such lack of ambition is OK after all. The man “had a good life all the way.”

15. Both Sides Now, by Joni Mitchell, as sung by Joni Mitchell

The last time I was on a plane, I looked out the window and saw a bank of particularly fluffy clouds – below me. I inevitably thought of this song, and of how “I still don’t know clouds at all.”

14. My Heroes Have Always Been Cowboys, by Sharon Vaughn, as sung by Willie Nelson

This song and Willie Nelson’s tumbleweed-in-the-wind voice are the perfect marriage, and end up perfectly portraying the used-up fate of a drifter.

13. If It Be Your Will, by Leonard Cohen, as sung by Antony

This is one of the few songs that Cohen wrote that is sung better by someone else. Antony’s version is unearthly beautiful.

12. Starry, Starry Night, by Don McLean, as sung by Don McLean

This was one of my favorite songs even before I knew it was the story of Vincent Van Gogh and before I knew how perfectly it reflected Van Gogh’s talent and struggles. “The world was never meant for one as beautiful as you.” With all my youthful angst and ego, I thought the song was made for me.

11. Forever Young, by Bob Dylan, as sung by Rod Stewart

The qualities and the kinds of luck needed to maintain a youthful spirit are beautifully rolled out here. Stewart’s video is also irresistible, with the young boy who’s riding along on his lap - tweaking his nose as they go.

10. Strange Fruit, by Abel Meeropol, as sung by Billie Holiday

This song contains what is perhaps the most searing metaphor in all of English literature. With Billie Holiday singing in her calm, liquid, almost matter-of-fact tone – the horror of racism is brought home all the more keenly. A 96-year-old friend of mine said she came upon a couple of trees hung with this fruit as she was walking through the woods outside of Macomb, Georgia, in her youth.  

9. Endless Road, by Hoyt Axton, as sung by Hoyt Axton

The beautiful harmonics of this song lead the listener home. When Hoyt Axton, who arguably had “the best pipes in the business” forms that final chord with the music – it’s chillingly beautiful.

8. September Song, by Kurt Weill and Maxwell Anderson, as sung by Willie Nelson

This is a timeless reflection on love sustained through the long years.

7. Blowin’ in the Wind, by Bob Dylan, as sung by Odetta

This has rightfully been the anthem of the Civil Rights movement and of freedom movements everywhere. It was likely a key element in winning Dylan his Nobel Prize for literature. As a result of my having joined the Student Nonviolent Coordinating Committee when I was in high school, a classmate wrote a stanza from this song in my graduation book. The song is eternally relevant.

6. Sunday Morning Coming Down, by Kris Kristofferson, as sung by Johnny Cash

This song perfectly captures the retirement quality of Sunday mornings. No job to go to, not many stores open, not many people out, no mail delivery, nothing at all coming your way. Even the sun seems to shine gray on these Sundays. It only sheds enough light for you to sit and notice the dust filtering through its rays, with no stir in the air - settling down and covering your furniture, your life.

5. Love Me Tender, adapted by Ken Darby from Civil War ballad Aura Lea by W. W. Fosdick and George Poulton, as sung by Elvis Presley. (Aura Lea version sung by Frances Farmer)

The minimalist version of this song that Elvis sings in his movie debut is the ultimate demonstration of how moving a simple song, sung by someone whose voice has a beautiful timbre – can be.

4. This Land Is Your Land, by Woody Guthrie, as sung by Pete Seeger

This song should be our national anthem. Its rousing, welcoming, all-embracing spirit is America, or what America should be. Now they call it “inclusiveness” – a quality this song has in abundance, without being self-conscious or politically correct about it.

3. Over the Rainbow, by Harold Arlen and Yip Harburg, as sung by Judy Garland

This classic needs no commentary.

2. Good Ole Boys Like Me, by Robert McDill, as sung by Don Williams

This poetic narrative of a song speaks volumes. It distils the works of Faulkner, Tennessee Williams, and other southern writers, into a glass of smooth bourbon. It speaks for the southerner who has been disenfranchised in the modern world, whose plight and heartache is disregarded in the rush to give priority to the disenfranchised represented in rap music. But there’s pathos in the way the poor white southerner has come too. When an acquaintance of mine proudly tells me how his father thumped the Bible and thumped him a whole lot harder - I hear the strains of this song. When I see the incomprehension in his eyes as he’s confronted by this world of political correctness – I hear the strains of this song. As he walks away from me, in beleaguered, impotent rage at my suggestion of evolution and equality, I hear the central question of this song - “So what’ll you do with good ole boys like me.”

1. Blue Skies, by Irving Berlin, as sung by Harry Richman

This song, seemingly such a simple ditty, has that underlying complexity that makes for a great song. If it’s sung at a cheery pace, there is still that inevitability of tragedy hiding behind the lilt, peeking out. If it’s sung as a slow blues wail, there is still that inevitability of joyousness peeking out. I had a hard time finding a singer who allowed this split personality to reveal itself sufficiently. It seemed that Harry Richman’s version came the closest. Richman, one of my favorite singers, had the advantage of singing the song close to the time it was written, when that 1920’s singing style usually had the in-a-tunnel, megaphone quality that carries such an automatically touching resonance. It automatically evokes a combination of nostalgia and happy expectation.

It’s hard to sing this song badly, but in my opinion, Al Jolson, another one of my favorite singers, uncharacteristically accomplishes that butchering when he bursts out with his eye-rolling, chopping- block rendition of the song in The Jazz Singer, the movie credited as being the first “talkie.”

In any case, the song was the first song to be heard when the modern media era was ushered in, and it might well be the last song to be heard when our time on this planet comes to an end. Then it will be “nothing but blue skies, from now on…”