My Favorite Recordings of Popular Songs

Last year, I did a multi-series of posts that went into 100 of my favorite showtunes of all time. Now, while I know that a good amount of theatre fans read this blog, I also know that the showtune love is limited.

I do have an interest in music beyond Broadway…but it is certainly not the same as most people that I grew up around. I was always drawn to the oldies as a kid and especially grew to love the singers who prospered in the Big Band/Swing era (Judy Garland, Nat King Cole, Lena Horne, Sinatra, Dean Martin, Ella Fitzgerald, Peggy Lee…you get the idea). I feel like some of my music tastes could even surprise some of you as I don’t often express my passion on various groups/singers…but this list isn’t really going to necessarily my favorite songs per se. They are most certainly some of my favorite songs but I am specifically choosing these particular recordings of these songs as being the definitive example of each.

Taking all of that into account, I will be considering my love of the song itself, the vocal performance of the song, the orchestration of the song, and the general mood it conveys. Also, these will not be showtunes; These are songs that began life via records/radio….and songs from movies will be considered in this case. One last requirement I am going to stick with is limiting each singer to one song.

#10-KILLING ME SOFTLY WITH HIS SONG: performed by Roberta Flack

This was a song that was originally performed by a white woman, Lori Lieberman. It’s a nice version, but leave to a black woman to show her how it should be done.

Part of the reason that Roberta Flack’s version took off and Lieberman’s didn’t could be due to the simple fact that Flack gave it a driving beat (which The Fugees also did in their own way to exceptional results as well).

This is a song, which I will sort of address in other selections coming up, that I’ve never quite understood why I loved it as much as I do.

It’s mostly quite simple in its approach and execution, but Flack’s voice along with the subtle harmonies and the soulful beat just add up to make a truly classic song. There is also this sort of sensual personal edge to it which I think gives it a lot of flavor as well.

I would recommend looking at the Lori Lieberman version for comparison with Flack’s:

Lieberman’s version is lovely in its own right. It feels very much like a Joni Mitchell song.

#9-WHERE DID YOU SLEEP LAST NIGHT (IN THE PINES): performed by Kurt Cobain/Nirvana

As a child of the 90s, I was definitely aware of Nirvana and the suicide of its frontman Kurt Cobain.

I never bought into the Grunge aesthetic in the slightest and definitely felt more drawn to polished styles at that time…but I was also a kid who basically rejected his West Virginia surroundings and wanted an urban life.

Looking back on the 90s now, I don’t necessarily like the Grunge aesthetic but I can’t deny that I do still like certain qualities in guys that show a little roughness around the edges.

Cobain was a sexy man to me, but a lot of that had to do with his face more than his shabby clothes. However, Cobain possessed a raw quality as a performer that I think was unmistakably dark and emotional and raw.

The NIRVANA: UNPLUGGED album is a masterpiece and the fact that it was also filmed live is an absolute gift. While this song was a Lead Belly cover, I still distinctively remember the first time I heard it and Cobain shrieked out at the end and then briefly opened his eyes…it could be in retrospect but it truly felt like we were getting a quick glimpse into his tortured soul.

Cobain may not impress or please those looking for singing that is technically perfect, but Cobain was a master at conveying emotion…and it’s a shame that once he got the fame he originally craved, it destroyed him. I would’ve loved to see where he ended up today had he kept performing.

#8-WHITE CHRISTMAS: performed by Bing Crosby

And now for something completely different….

I am a Christmas freak….I always have been. I do not tire from Christmas music during the holiday season and I am one of those people who actually anxiously awaits Halloween to be over so that Christmas can start creeping in.

WHITE CHRISTMAS is such a definitive holiday classic, which is not surprising as it was written by Irving Berlin who was the forerunner of creating music that would define “The Great American Songbook”.

As written for the movie HOLIDAY INN, the song was first popularized by Bing Crosby, who…if I may make a morbid joke…took a break from beating his kids just so he could give us this warm soothing holiday treat.

Yes, Crosby was one of many heinous human beings from that era in Hollywood (something I guess hasn’t really changed), but there is a reason this particular record was the best selling Christmas song ever.

While it isn’t my favorite Christmas song, I can’t deny that it is the definitive song for the holidays for me.

#7-A CHANGE IS GONNA COME: performed by Sam Cooke

The King of Soul…and someone I feel like often isn’t as mentioned as other people. I mean they called James Brown “The Godfather of Soul”…and frankly that’s a title he deserved because he was a stellar performer.

Sam Cooke was a very suave and passionate singer who was basically, to quote AllMusic biographer Bruce Eder: “the inventor of soul music…possessed an incredible natural singing voice and a smooth, effortless delivery that has never been surpassed”.

I would say that’s fair, especially if we are speaking for male singers.

A CHANGE IS GONNA COME was his last big hit before he was murdered in a rather questionable incident at a hotel which the LAPD (no surprise as they are the WORST) had passed off as a “justifiable homicide”.

I think every song he did was quite wonderful but I think this song is basically the epitome of soul music. Also, very few songs have as stellar an opening as Cooke’s “I was BOOOOOOOORN by a river!”

#6-SAVING ALL MY LOVE FOR YOU: performed by Whitney Houston

There was no question that Whitney Houston was going to be on this list. The biggest problem for me was choosing which song to go with.

While I might listen to a couple of her songs more often than others, I ended up settling on SAVING ALL MY LOVE FOR YOU, which came from her debut titular album.

The choice sort of even surprises me, but it almost came to my mind instantly when thinking of her songs. It’s a beautiful, jazzy, soulful arrangement while also having that distinctive 80s sound…and on top of that, it gives Houston the chance to go up and down her range from sweetly purring up to belting her head off and giving us some lovely head voice.

Judy Garland was my favorite singer/entertainer, but if you strictly base it on the quality of the voice, I feel like Whitney Houston was the greatest singer we’ve ever had.


This is her performance of the song on David Letterman back in the 80s…and it is truly fantastic.

And below is her performance of the song on the Grammy Awards in 1986. This performances wowed people so much that she actually WON A FREAKING EMMY FOR IT! That kind of thing never happens with Grammy performances.

#5-YOU MAKE ME FEEL LIKE A NATURAL WOMAN: performed by Aretha Franklin

Originally written by Carole King and Gerry Goffin, with the former even recording it herself, I think most people recognize this song more solely with Aretha Franklin, who was undoubtedly one of the greatest singers to have ever lived.

I do think there was quite a bit to Franklin’s catalog that gets overlooked when compared to songs like RESPECT or even this song, but I have always been drawn to this one. It can be hard to explain why certain songs get to us but I think a lot of what drove me to really liking this song was the fact it just sounded so unique.

I very much loved the soulful/R&B sound in music that came out of Motown and would grow more in the 70s, and I think this song was part of that tradition.

It is a wonderful arrangement of the song and I certainly can’t deny that Franklin deserves a lot of credit here.

#4-CRAZY: performed by Patsy Cline

Patsy Cline is often considered by historians to be THE greatest country music singer of all time. I am not sure I personally feel that…I can’t say I’ve given it too much thought recently. I do, however, acknowledge that her voice is magnificent and that her tone/timbre is so distinctive that you can’t help but recognize her within a mere note or two of singing.

My selection of CRAZY really comes down to the combo of her voice and the quality of the song and how simplistic the record was produced.

It tells a story that is very relatable to pretty much anybody; she gets to show a nice range of her voice; and it is also an example of how Country music isn’t a genre that should be completely discounted….just keep in mind that you probably have to go back to the 50s-70s to find the better stuff.

#3-THE MAN THAT GOT AWAY: performed by Judy Garland

I sort of chose this at random a little bit. I used to acknowledge this as my favorite performance of a song years ago, but I am not sure I can make that claim now. I do still acknowledge it as a truly definitive piece of work and since I always proclaim Judy Garland to be the best (or “the GOAT” as you young Gen Z people say…), I wanted to include her here.

As most of you probably know, this song was written for her to be performed in a scene from the 1954 remake (the 2nd of 4 movies from this series): A STAR IS BORN.

We tend to forget that at one time, the popular music of the day were songs that did come from movies or, gasp, the musical theatre scene. A lot of that changed going into the 50s and 60s while most of Broadway just sort of remained in its own corner (with the exception of stuff like HAIR or songs like “Send in the Clowns” which seemed to have taken off by accident)…and the same could be said for a lot of movie songs too.

Nevertheless, this song is often listed as being one of the greatest to come from a film…and I certainly resist Judy Garland singing what may be the most ultimate torch song there is.

#2-GEORGIA ON MY MIND: performed by Ray Charles

“Wait…isn’t this the theme song for DESIGNING WOMEN?”

Yes, younger Anthony…it is. It is also the state song for Georgia, too.

I LOVE this version so much…like I truly think it is a stunning piece of work. I honestly think this is practically a tie with what will be my #1 song…but for now, let me explain my love for this song.

……can I really explain it??

The song existed for many years prior to Ray Charles recording it, but his arrangement made it seem so haunting and sentimental without being the least bit cloying. He was a master at entertaining and working the crowd with his soulful voice and even though this is one of his subtler efforts, I think his vocal performance here is still pure perfection.

It’s also remarkable that I once heard this song every day up to twice a day. Back when I worked for UPS, I would often be the only one in the office in the morning before my colleague would show up two hours later. I got into the habit of playing Big Band music on Pandora and every day, like clockwork, this song would play. It got to a point where it would repeat when my coworker would come in and he’d comment on how it seemed like I never tire of this song because I would never skip it when it came on.

I just think it is one of those songs where they truly captured lightening in a bottle with the arrangement they created. A truly astonishing record.

#1-STARDUST: performed by Nat King Cole

As I said, this was really a close call to the point of being a tie…but I am still going to give STARDUST my #1 selection. Here is why that is the case: I feel like this song, and also my love of jazzier music came from, of all things, the movie SLEEPLESS IN SEATTLE. That movie came out when I was only 5 going on 6 years old and I just distinctly remember hearing the soundtrack of that film and finding it very unique…especially considering my childhood up to that point had been devoted to country music (yes, I am not kidding…there was a time in the early 90s when yours truly was obsessed with CMT like most people were with MTV….)

STARDUST is a song that had been around long before even Nat King Cole recorded it (just like Ray Charles with GEORGIA), though I feel very comfortable saying that most people do still associate the song with him. For me, his version literally feels like you are walking on a pier by the water at night watching the lights twinkle whether they be the stars or stand-in stars from the skyscrapers around you. When I first moved to New York, I went down to the pier off of Christopher St in the Village and walked along the Hudson River as the sky loomed dark and I played this song…and make fun of me all you want…but I actually teared up. It felt like a fantasy of mine was coming true in some way that I was finally living in the art deco bubble I longed for since I was a child.

I would be remiss if I didn’t mention more about Nat King Cole. He is my favorite male singer and I know that might raise some eyebrows. His voice was not boisterous or even impressive in terms of range, but he had the voice of silk (ironically considering his smoking habit…which he thought HELPED his voice but only led to his death in 1965). I would say he, along with Karen Carpenter, have the market cornered when it comes to voices that just feel like pure soothing bliss.


There it is…and perhaps some of these songs wouldn’t be featured if I made this list a week from now. That’s okay…it’s a snapshot in time; I just felt the need to discuss and share these songs. I wasn’t able to fit a lot of my favorite singers on this list even though I might like them more than some of the people I put up here like: Karen Carpenter, Ella Fitzgerald, Lena Horne, Eydie Gorme….you can tell I love the women singers most.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Blog at

Up ↑

Create your website with
Get started
%d bloggers like this: