DJ OldsKOOL’s Top 53 Songs of All Time

The Scenario: I’m trapped on a desert island. I get one CD (set) with 53 songs. Why 53? Because it’s a prime number and it’s my list.

This was incredibly difficult to compile, but a lot of fun. Not all songs are great songs by industry standards, but they are great to me for different reasons.

If you have nothing to do, take your time and try this. It’s not easy. It took me several months, but it was a blast! The list with my commentary is below, but you can download a PDF of just the list here >>

The List

No 53: Steve Earle, Justice in Ontario, 1990
The CD needed a shot glass of Steve Earle’s sound. This rock ballad tells the story of the murder of The Black Donnellys, so it has historical significance. And it has Earle’s voice. Good enough!

No 52: Sonny Boy Williamson, Bye Bye Bird, 1964 live show
What this incredible man did with a harmonica is unbelievable. A one-man band and a blues treasure. Blues welcome on my island!

No 51: Edith Piaf, La Goualante du Pauvre Jean, 1957
The biggest problem with her is what song to choose. This is a great upbeat classic sound that makes you want to break out the top hat. “Sans l’amour on est rien du tout”

No 50: Roger Miller, King of the Road, 1964
There was a smooth side to 60’s music too, and I think this one captures it well. This is one of those 4-beer-buzz songs on a windless, quiet day on the island.

No 49: Elton John, Candle in the Wind, 1973
Just a really pretty song among many of his pretty songs. It was dedicated to Marilyn, and re-dedicated to Princess Diana.

No 48: Janis Joplin, Cry Baby, 1970
She took that 60’s hit and tore it up Joplin style. When I was a kid, I could hear that Pearl album at night playing in the basement of our old house courtesy of my sister. Way to get to sleep!

No 47: David Bowie, Diamond Dogs, 1973
Great raunchy rockin’ tune. The album art was great, so was the exhortation by Bowie at the beginning. Second album I ever bought. I was 12. Still sounds great after 39 years!

No 46: Iggy Pop, Real Wild Child, 1986
Errr, speaking of raunchy. Love him or hate him, you have to admit that he can rock an audience. This song is a blast.

No 45: Guns N’ Roses, Sweet Child o’ Mine, 1987
One of the best songs from one of the best albums of all time from one of the best groups of all time. The prosecution rests.

No 44: The Doobie Brothers, I Cheat the Hangman, 1975
A haunting song from a somewhat forgotten band. They could do incredibly melodious music and this is an excellent example.

No 43: Patsy Cline, She’s got You, 1962
She was a pioneer, a phenomenal singer and an awesome example of how great country music can be. It was a toss up between I go walkin’ and this one – can’t go wrong either way.

No 42: Bill Withers, Lean on Me, 1972
Songs don’t get much more beautiful than this. I believe it was also used in a wonderful movie called Sounder that same year. This is one of those songs that should never be covered. Just leave it be and thank the Universe for giving you ears.

No 41: Emerson Lake & Palmer, C’est la Vie, 1976
ELP were a superb progressive rock band throughout the 70’s and I love them. But I always had a soft spot for Greg Lake’s amazing voice. He also fronted those great early albums from King Crimson.

No 40: Downchild Blues Band, Flip Flop & Fly, 1973
Here’s to one of the most underrated blues bands in the world, and all-Canadian to boot! Whether it was the old Walsh version or the Chuck Jackson led sound it’s all the same – superb!

No 39, Paolo Conte, It’s Wonderful
Maria introduced me to him in 2003. I can’t make out any of the words other than “Chips Chips”, “It’s wonderful” and “Good luck my baby”, but it don’t matter. It’s a feel-great song. Thanks to Maria Ford for introducing me to this artist.

No 38, Chris Isaak, Wicked Game, 1991
This is one classic song. He has one of the most spectacular voices ever. We’re talking Elvis quality here.

No 37: Dire Straights, When it Comes to You, 1991
One of my favorite bands of all time. I know that to most people there are a dozen Knoppfler pieces that are more worthy, but this one embodies country – which he is very good at – and his impeccable guitar.

No 36, Peter Gabriel, Biko, 1980
It’s about Steve Biko, it’s powerful, and it belongs on the island.

No 35, Kid Rock, All Summer Long, 2008
It’s a magnum of Kid Rock with a chaser of Lynyrd Skynyrd and some Warren Zevon peanuts on the side. Never get tired of it.

No 34: Harry Chapin, Cat’s in the Cradle, 1974
70’s folk rock at its very best. I wonder what he would have been singing if he had been around here longer. He passed way too young.

No 33: The Band, The Weight, 1968
Robbie Robertson must have been really shit-faced when he penned this classic. I still don’t understand what it’s all about, and I don’t care – it’s all music to my ears.

No 32: Louis Armstrong, What a Wonderful World, 1968
Just a beautiful song from a beautiful artist.

No 31: Buddy Holly, That’ll be the Day, 1958
Rock and Roll V1.0. Great rhythm to this song.

No 30: The Beatles, Hey Jude, 1968
How do you pick a Beatles song? You could probably have 53 of them on the island and not get bored – as long as there are none where Ringo is singing. LOL!

No 29, Al Stewart, Roads to Moscow, 1973
An epic song. Supposedly tells of Alexander Solzhenitsyn’s experiences in WW2 and beyond, but could probably apply to thousands of Russians who wound up in the Gulags. Powerful, powerful song.

No 28, Benny Goodman, Sing Sing Sing, 1936
Ever seen the clip of him playing at Carnegie Hall? This guy was another pioneer, and this song will definitely make the monkeys dance on the island!

No 27, George Michael, Cowboys and Angels, 1991
I know I’ll take heat for this, but it’s a great jazz song, the man has a wonderful voice, and this song is just silky. It’s actually written to a waltz tempo.

No 26: Ray Charles, Georgia, 1960
Love this song. Love it so much I named one of my shi-tzu puppies Georgia, and used to sing her that song. She would grunt and snort.

No 25: Del Shannon and the Vikings, Runaway, 1961
Makes me wanna grease my hair, wear a white T with the smokes tucked under the arm, and go rippin’ around town in an 58 Chevy with tuck and roll upholstery.

No 24: Tom Jones, Green Green Grass of Home, 1966
Another power voice that the island can definitely use. Classic song, classic artist. Did you throw your panties at him back in the day?

No 23: David Johansen, Animals Medley, 1982
AKA Buster Poindexter (& former New York Dolls member) paid tribute to the incomparable Eric Burdon & the Animals with this awesome awesome live medley. Rock out!!!

No 22: Gordon Lightfoot, Wreck of the Edmund Fitzgerald, 1976
Great storytelling, close to home, haunting and chilling with its backdrop of actual radio conversations with the coast guard.

No 21: Bob Dylan, Knocking on Heaven’s Door, 1973
Sure GnR’s version was killer, but this is the original – pure, pristine, Dylanesque.

No 20: K D Lang, Hallelujah
She has one of the most beautiful and powerful voices in all of eternity. Nobody sings this great classic like she does.

No 19, Neil Young, Unknown Legend, 1992
It was a toss up between this and Old Man. This is from Harvest Moon – by 92′ he already had 20+ albums out. He went back to acoustic and recorded in Nashville. The lyrics are powerful, and it makes reference to a motorcycle, so it wins the toss.

No 18, John Hammond (w. Tom Waits), I Know I’ve Been Changed, 2001
John Hammond did magic with his cover of Waits songs in 2001. For me this is one of the best blues albums of all times. Thanks toMaria Ford for discovering this gem. It never gets old or tired.

BONUS TRACK! No 18b: Deep Purple, Lazy, 1972
This is the song that got me started on the Top 50 countdown. I was thinking how great a song this is, then asked myself, just how great is it? One thing led to another and voila!

No 17: Marvin Gaye, Let’s Get it On, 1973
Another genius singer that we lost way too early. If music is a rainbow, Motown is the pot of gold at the end.

No 16: Dire Straights, Romeo and Juliette, 1981
Great ballad from a great band. Knoppfler’s picking is always picture-perfect, and his voice is one of a kind.

No 15: Queensryche, Silent Lucidity, 1990
Power ballad. Beautiful song. Unbelievable orchestration.

No 14: Crash Test Dummies, Superman, 1991
This is such an elegant song. It says  alot, about a lot of things that just aren’t right with today’s world. In that sense it’s very sad. And that voice, that voice…

No 13: Van Morrisson/The Band, Comfortably Numb, 1990, Live
Van the man and The Band covered this epic Pink Floyd song when Roger Waters did The Wall show in Berlin. This was a landmark event (The Band were pretty decent at backing up Sinead O’Connor on Mother too).

No 12: Amy Winehouse, Wake Up Alone, 2006
Wow could she ever destroy it! Command performance style. She was a musical treasure.

No 11: The Blasters, One Bad Stud, 1984
Epic jump blues cover by one of the masters – Phil Alvin. You might remember this song from the movie Streets of Fire (bar scene, bikers, stripper, Willem Dafoe in Lycra).
“He just hangs on the corner singing old country blues’

No 10: Billy Idol, Sweet Sixteen, 1986
Great ballad from a great rocker. Though I love a lot of his stuff, this song shows off his soft side. He clean up real well.

No 9: Tragically Hip, Wheat Kings, 1992
This one was dedicated to David Milgaard, a Canadian who was wrongly convicted of murder. Canadiana from a Canadian Band and a great one at that. If U don’t know The Hip, you’re missing out big time.

No 8: Johnny Cash, Hurt, 2002
Songs don’t get any more intense. The video is chilling, as is Cash’s frail, un-miked voice. Perhaps one of the greatest videos of all time, but the song doesn’t need video to be incredible. John can do that all by himself.

No 7: Etta James, I’d Rather Go Blind, 1968
She had the perfect voice that never failed, stumbled or growled. And so much soul. If there’s a heaven, the angels all sing like her.

No 6: Mamas and the Papas, Dedicated to the One I Love, 1967
Terrific cover. Love the song, love this version. Cass Elliott, you were something else.

NUMBER 5: ELVIS PRESLEY, BLUE CHRISTMAS, 1957
For me, a no-brainer – the King, a XMas song, and my favorite Uncle’s (the one who would hold me on the old bicycle frame while flying down the steepest hills and who drove his car at 100+ mph with me in it) favorite song.

NUMBER 4: BO DIDDLEY, BO DIDDLEY, 1955
The man who started it all. What an awesome cat! Check out his videos too – the man could move!

NUMBER 3: JOHNNY CASH, BIG RIVER, 1958
Love that BIG voice and that BIG, simple picking. His early, trademarked 3-chord sound was supposedly because Luther and the boys only knew 3 chords. Never met a Cash song I didn’t like.

NUMBER 2: SMOKEY ROBINSON, THE TRACKS OF MY TEARS, 1965
Magnificent Motown don’t get much better than this. And shout out to Boyz2Men who did a great cover not so long ago.

And here it is, Number One: JOHN LENNON, IMAGINE, 1971
It’s all about hope. From the Gretzky of musicians. Not the greatest at anything, just the greatest overall. Thanks for tuning in and I look forward to seeing some of your lists!

Download the list (PDF) >>