My Ten Favorite Songs

of the 20th Century

Favorites are personal, not meant to be everyone’s jam. I make no claim of Best-ness. What is a song anyway? Something you sang over and over at summer camp? Something your mother sang to you when you were very young? This list focuses on songs that were recorded and became popular. Maybe lullabyes and early sing-alongs create a groove that helps make something popular into a personal favorite.

The sixties, my coming-of-age time, is well-represented with six of my ten favorite originating at that decade. The fifties gets two songs and the eighties and nineties one each. I made this list in 1997, except it was not one list. I separated rock and blues and jazz. I am combining three lists into one as I write these blurbs now, looking back from 2025.

• Where or When, Erroll Garner 1955

• MTA, Kingston Trio 1959

• Mack the Knife, Body Darin 1959

• Stay, Maurice Williams & the Zodiacs 1960

• Baby Please Come Home, Darlene Love 1963

• I Can’t Explain, Who 1965

• I Got a Mind to Give Up Living, Paul Butterfield Blues Band 1966

• You Ain’t Going Nowhere, The Byrds 1968

• Cherry Bomb, John Mellencamp 1987

• Autumn Leaves, Eva Cassidy 1997

Where or When, Erroll Garner, 1955

This song has nothing to do with lullabyes or singing along and everything to do with sitting back and appreciating a musical genius. This instrumental is the climax of what many consider to be the finest live jazz piano performance ever recorded. It is a fluke that it was recorded at all. Thank you, universe. I also thank my father for playing the whole, “Concert by the Sea” album whenever my mother was out. The relentless drive of Erroll Garner’s orchestral piano was too much for her and became a sound I have loved ever since. I have listened to his version of the jazz standard, ‘Where or When’ probably a thousand times and it still gives me goosebumps when he takes off on those fast scales over and over repeating himself near the end.

MTA, Kingston Trio, 1959

This song drew me and thousands of kids like me into popular music. What helped the Kingston Trio, in my opinion, launch the 60s, was the sing-along factor. They invited participation. They were the opposite of pop idols – you could do what they did. Their songs were easy to sing, so we did. ‘MTA’ is now deeply embedded into American culture and why not? It’s has a catchy tune, some excellent and humorous banjo work, and a memorable narrative with compelling episodes -- plus it’s making fun of capitalism. Stories are supposed to have a beginning, middle, and end. The ones that don’t have a way of staying around.

Mack the Knife, Body Darin, 1959

I looked up at my father the first time I heard this song, coming out of the car radio in our old Chevy, like, ‘a song can really be like this?’ He nodded. He liked Bobby Darin and anything with drive and swing because in actual life they were both hard to come by. Mack was a terrible role model and here he was on the radio. Now I know a lot more about “The Three Penny Opera” and the Weimar Republic and where Bobby Darin fits in jazz history and it’s still inexplicable how ‘Mack the Knife’ can be one of the most popular songs of all time. It’s my go-to song for Karaoke. (#251 on RS2006 and RS2021)

Stay, Maurice Williams & the Zodiacs, 1960

Most great songs have a great back story and this one is both great and predictable. The whole song came to Maurice Williams in one big rush in 1953 when he was 15 and his date turned him down his request for something more. It is so improbable that the song was ever recorded, that it was heard by anyone, then heard by millions. It is the shortest song (1:36) ever to reach #1 on Billboard. The Hollies and the Four Seasons brought it back and Jackson Browne gave another life in the 70s, which is when I really began to appreciate it. Later, Rihanna did it her way and the Kid Laroi and Justin Bieber produced another good version It’s partially the length and partially its featured attractions, like the way Maurice pleads his case, then the falsetto, and the doo-wop styling – this is a song I can binge play, ten times right in the row.

Christmas -- Baby Please Come Home, Darlene Love, 1963

If you haven’t seen Darlene Love sing this song on The David Letterman Show, in her 80s, you haven’t seen what a lifelong pro and a true live performer can do with a song at any age. I remember when it first came out, but she was lost to me at the time in a flood of Phil Spector ‘girl groups’ and then something else called Motown. ‘Baby Please Come Home’ didn’t hit the charts until 2014, over 50 years after its release. Now it’s a Christmas standard. I think it transcends the genre. (#485 on RS2021)

I Can’t Explain, Who, 1965

Every changed after ‘My Generation,’ which placed #12 on Rolling Stone’s 2004 Top 500 Songs List. The Who came right out and said it like no one else: why don’t you all just f-f-f-f-fade away, don’t try to dig what we all say. Don’t trust anyone over thirty never made any sense to me, but, hope I die before I get old does. It was an anthem and I love it but nowhere near as much as I love Can’t Explain. It’s short and it’s another song I can put on repeat ten times in a row. I find Townsend’s guitar open even edgier and more compelling than Keith Richard’s more famous riff on Satisfaction. No one attacked instruments like Townsend – except Keith Moon. I saw them play this song live in 1966 at a smallish venue in Rochester, New York where they were opening for Hermans Hermits. (#382 RS2021)

I Got a Mind to Give Up Living, Paul Butterfield Blues Band, 1966

In a college dorm room back in 1967, I heard a guy who knew much more about music than I did say, ‘that’s the best guitar solo ever recorded’ while listening to Michael Bloomfield give up living on ‘East-West,’ which he eventually did for real at the age of 37. I loved that song before it became imbued with all the meaning of the Michael Bloomfield story. There have been countless ‘best-guitar-solos’ since those early days of modern blues and blues itself has come to be considered technically more constrained than rock or jazz. Those so-called limiting factors brought out the best in Michael Bloomfield. Shopping ain’t living but playing blues is.

You Ain’t Going Nowhere, The Byrds, 1968

The Byrds did Dylan hands-down better than anyone else has done Dylan’s songs, not just once like Manfred Mann and ‘The Mighty Quinn,’ but over and over and in different musical styles. The synthesis of country and rock may not begin with ‘Sweetheart of the Rodeo,’ but this exceptional album brought it into or at least close to the mainstream. ‘You Ain’t Going Nowhere’ is a recognizably-Byrds song, with crazy Dylan lyrics and a new rhythm that’s easy on the ears while delivering a harsh and real message.

Cherry Bomb, John Mellencamp, 1987

JCM is a Rock ‘N Roll Hall of Famer, but Top Ten? This is a Favorites list and it’s not about John Cougar Mellencamp. It’s about the song. It’s flow, how danceable it is, how cool he moves in the video. What puts it on this list is the story it tells, everyone’s story. Where did the years go? Our kids think of us as grown-ups but we’re still young and we wonder about the improvin’ part. I’m a few years older than JCM but while I was writing this piece I thought about when holding hands meant something and ended up crying, as if to affirm this song’s rating in my pantheon.

Autumn Leaves, Eva Cassidy, 1997

We might have thought that Miles Davis’ 1991 take on this standard of standards was the final word, in the way that Fukuyama declared the end of history a year later. Well, liberal democracy isn’t quite the invulnerable powerhouse it might have looked like 35 years ago and Eva Cassidy took ‘Autum Leaves’ and made it into something I’d never imagined. I like ‘Autumn Leaves’ so much I collected different versions – from Dizzy Gillespie to Tito Fuentes – and put them one after another on a CD, back when there were CDs. That was before I even knew about Eva Cassidy. Completely Reinterpreting a tune millions of people love and are used to isn’t playing it safe. Nothing in how she sings this beautiful and emotional song plays it safe. I listen to it all year long.