The greatest pop voices of our time. Day 1: Sinatra

This week I’ll feature what I think are the four greatest pop singers—in terms of vocal quality—of our era.  There will be two males, two females, and then, on Thursday and Friday, the also-rans.  I’m not necessarily highlighting singers who are great stylists, or vocally inventive, but those whose voices simply give me the most pleasure.

I’m sure that at least one of my choices will be controversial, but the first one is not. It’s Old Blue Eyes, here singing the George Gershwin classic, “Our love is here to stay” (recorded in 1955, lyrics by his brother Ira Gershwin).  As in this instance, Sinatra did his best work with conductor/arranger Nelson Riddle.  I’ll try to feature live performances, but there’s not one of Sinatra doing this song.

Gershwin, who died of brain cancer at age 38, wrote so many great songs, including “I Got Rhythm,” “They Can’t Take That Away From Me,” and “Summertime” from his opera Porgy and Bess.  Imagine how much more music we’d have if he’d lived a normal span!

And Sinatra, of course, always gives an impression of effortless musicality in his songs.  Is there anyone who doesn’t like him?

Click on “Watch on YouTube”.

For a great jazzy version of this song by Ella Fitzgerald, click here. Want live Sinatra? Try here, here, and, for a LOLzy duet with Dino, here.

And, of course, you’re welcome to tout your own favorite artists or songs.


  1. NewEnglandBob
    Posted February 20, 2011 at 6:44 am | Permalink

    And this is not the best from either Sinatra or Gershwin, but is still great.

  2. Sili
    Posted February 20, 2011 at 6:59 am | Permalink

    Is there anyone who doesn’t like him?

    Yes. If you don’t restrict the liking to his voice.

    • Dominic
      Posted February 20, 2011 at 2:06 pm | Permalink

      Ah yes – the art & the artiste – you can like the one & dislike the other.

  3. joe
    Posted February 20, 2011 at 7:03 am | Permalink

    even disregarding his vile behavior, i don’t like him. i’ve never heard him sing a word that sounded like he MEANT it.

    • chemicalscum
      Posted February 20, 2011 at 7:19 am | Permalink

      Agreed – Sinatra puke !

    • Sven DiMilo
      Posted February 20, 2011 at 9:10 am | Permalink

      There’s no accounting for taste, eh?

      I think you’re a nut.

      • chemicalscum
        Posted February 20, 2011 at 9:59 am | Permalink

        No – you have no taste

        Sinatra – Boredom, Boredom

        • whyevolutionistrue
          Posted February 20, 2011 at 10:04 am | Permalink

          okay, enough of this trolling. You’re rude and you’ve made your point. You don’t like Sinatra. Do you think that comment is even worth making here? Maybe an analysis of why he is bad would be prescient, but no, you just have to come to my house and be rude.

          Please go to someone else’s house.

          • Robert MacDonald
            Posted February 20, 2011 at 6:02 pm | Permalink

            Sam Giancana wore a friendship ring from Frank Sinatra.

            Do you want more of an analysis?

    • sasqwatch
      Posted February 20, 2011 at 11:58 am | Permalink

      I appreciate Sinatra’s style – esp. the nexus between the big band greats (e.g. Buddy Rich, who was another asshole [except I love his musical work])… but I feel compelled to dissent as well.

      What grates for me is the way his notes slid up into tune all the time. It’s a lazy vocalists’ trick, rather than just nailing those notes on tune. I suppose it’s more acceptable for single (esp. pop) soloists to do this, it just bugs me to no end. (I have accompanied choruses and small vocal groups – and in these contexts, doing what Sinatra does is a most grave sin. When more than one person does it, you get wolf tones up the wazoo.) To me, just the pitch aspects of what he does sounds to me like the vocal equivalent of a drunken trombone player.

      That being said, the bandwork backing him up was always tops. And I also was not exposed to him growing up (when your personality is really forming), so I lack the mental associations with holidays and other good times, which is what makes most music appealing to us no matter what it sounds like.

      • sasqwatch
        Posted February 20, 2011 at 12:05 pm | Permalink

        Faves in the same (or at least similar solo vocalist) genre:

        Betty Carter (way favorite) and Cassandra Wilson.

      • sasqwatch
        Posted February 20, 2011 at 12:29 pm | Permalink

        some examples of Betty and Cassandra that kill me. am hoping this doesn’t “embed” the vids.

        behind the scenes with Betty.

        and Cassandra:

        On reflection I’m OK with vocalists sliding notes – just not every damn time. It’s nice to know they are capable of extraordinary precision. None of the classic crooners or their emulators (Connick) do that for me.

        • JS1685
          Posted February 20, 2011 at 1:53 pm | Permalink

          Even in the classical world occasional scoops are OK. But only in rep from the late Classical era forward. The renowned vocal coach Russel Miller recommends as a heuristic: no more than one scoop per page.

          • JS1685
            Posted February 20, 2011 at 2:05 pm | Permalink

            Obviously, this applies to solo rep.

        • Dominic
          Posted February 20, 2011 at 2:11 pm | Permalink

          In a sense he did what many performers do who perhaps survive on natural talent rather than technique, the same can be true of sprts stars, so I think he was not able to sustain his voice in later life. Still find it a very pleasant voice – I am sure he may have had his faults as a human being but I do not know enough to comment.

        • Dave Ricks
          Posted February 20, 2011 at 3:37 pm | Permalink

          Your musical nemesis would be Sex Mob (e.g., Sex Mob Does Bond). Bandleader Steven Bernstein explains why he plays a slide trumpet: Almost every trumpet player has one. It is so hard to play that most people after messing around with it, go “F&*@ it!” The slide is so small if you are a tiny bit off, you sound like you are way off. Unless you are like me and you are totally shameless. Most people have too much pride for that. I like being a little off. I am hearing it like that anyway.

          • sasqwatch
            Posted February 20, 2011 at 8:16 pm | Permalink

            🙂 I’m going to have to find me some Sex Mob now. I just reacquainted myself with Shooby Taylor (the human horn), and I’m thinking I might need to modify my favorites list.

      • Filippo
        Posted February 21, 2011 at 10:00 am | Permalink

        So, Sinatra is apparently guilty of excessive “glissando.”

        One is able to presume to critique him on that because hitting a note spot on was part of “best practices,” so to speak back in the hayday of The Popular Standard of The Great American Songbook. I.e., back at a time when it was taken to heart that Prior Proper Practice Prevents Poor Performence.

        [I gather it won’t do to apply Yesteryear’s performance standards to 50’s R&R, 60’s/70’s Rock, 80’s Pop, and contemporary Rap (assuming that that is music in the first place). Surely readers here have seen film (1971?) of John Lennon in the recording studio chewing gum as if it were his cud before and during recording a song. I suppose that that did add “something.” Re: Jimmy Buffet’s “Margaritaville.” I didn’t want to sing the song in the first place, but, as I was part of a trio, our mutually agreeing to do some of each others songs, whether we liked them or not, was our reasonable, compromising – dare I say “accommodationist”? – modus operandi. So, I acquiesced. I was mildly but congenially chastised for basically not singing it “carelessly” (perhaps the better word is “insouciantly”?) enough.]

        Well, if Sinatra “scoops” (too often) when he sings, that’s not sat. But, should one expect him to sing a song the same way at least two times in a row? Not necessarily but, all else being equal, it’s good to be able to. Certainly, it’s not required of a soloist, but it inescapably is of a harmony vocal group, especially one like the Modern Vocal Jazz group, The Singers Unlimited (a foursome including two members of the the 50’s vocal jazz group, The Hi-Lo’s, contemporaries of The Four Freshmen) who dub numerous additional tracks, so they have to have the ability and self-discipline to sing the exact same rhythm and tempo repeatedly.

        So, I offer for your kind consideration at the below link the Singers Unlimited version of “Mr. Music”‘s and “Mr. Words”‘s “Our Love Is Here to Stay.”

    • SaintStephen
      Posted February 20, 2011 at 12:10 pm | Permalink

      Listen to Sinatra sing The Man In The Looking Glass. I think he “meant” that one.

      Can it possibly, be me?

      (I love the way he sings that line!) It’s also one of my earliest childhood memories, since my mother was a huge Sinatra fan and played his records all the time when we were toddlers.

      • SaintStephen
        Posted February 20, 2011 at 1:02 pm | Permalink

        Bingo! You can listen to a little snippet of the song (plus any others off that album) right here.

        • SaintStephen
          Posted February 20, 2011 at 1:12 pm | Permalink

          And since we’re all about scientific precision here (cough), the actual line is:

          Can he possibly, be me?

          P.S. Perhaps an even greater song off the September of My Years album is It Was a Very Good Year, which won Sinatra the Grammy in 1966.

        • joe
          Posted February 20, 2011 at 5:07 pm | Permalink

          that link wouldn’t work for me, so i went to amazon for a 30 second sample. and i appreciate the suggestion, but, no…it just conveys no sincerity…not to me, anyway.

  4. Posted February 20, 2011 at 7:56 am | Permalink

    Sinatra means Christmas for me–if my mother didn’t have that 8-track on at Christmas, my grandma did. Or my Great Aunt (though she was more likely, come to think of it, to have Perry Como or Lawrence Welk on…). I actually didn’t (or said I didn’t) like Sinatra when I was a kid. I don’t know when I decided I *did* enjoy listening to him–it sort of snuck up on me. I like JC’s version of Silver Bells, though ;-))

  5. Helen Wise
    Posted February 20, 2011 at 8:14 am | Permalink

    My father was a music slut. He loved, and listened to it all. He made his own mix tapes, using a Grundig reel-to-reel. I spent many hours in his shop with him, building model cars and planes, with Sinatra, or Tommy Dorsey, or the Rolling Stones, or Ella Fitzgerald, or Rachmaninoff playing in the background.

    He loved Sinatra the most, I think.

  6. El bastardo
    Posted February 20, 2011 at 8:53 am | Permalink

    Never liked Sinatra. Like other certain figures, I have no idea how he manged to get such a following.

  7. Sven DiMilo
    Posted February 20, 2011 at 9:12 am | Permalink

    Sinatra distilled Louis Armstrong and Billie Holiday together into the swingingest phrasing style of pretty much any singer of jazz-like music, ever.
    You can dislike his timbre, or whatever else about his ‘voice’, but no musician would ever criticize Frank’s phrasing.
    Always hip.

  8. Posted February 20, 2011 at 9:39 am | Permalink

    I can see this list is going to be interesting… I would never have even *thought* of Sinatra if you’d asked me to list great pop singers.

  9. 386sx
    Posted February 20, 2011 at 9:59 am | Permalink

    Frank Sinatra About 14,800,000 results (0.15 seconds)

    Justin Bieber About 328,000,000 results (0.22 seconds)

    • JS1685
      Posted February 20, 2011 at 10:08 am | Permalink

      Which just goes to show popularity =/= aesthetic merit.

    • Helen Wise
      Posted February 20, 2011 at 10:10 am | Permalink

      Well, Ozzie said it best: “What the fuck is a Bieber?”

      • Helen Wise
        Posted February 20, 2011 at 10:20 am | Permalink

        Pardon. That would be Ozzy, not Ozzie.

    • Torbjörn Larsson, OM
      Posted February 20, 2011 at 11:59 am | Permalink

      Yeah, I was also hit by “our era”.

      Luckily all this is subjective, because Sinatra sure doesn’t sing to me. (I find the style rather boring, though he seems technically proficient in it.)

  10. Bill
    Posted February 20, 2011 at 10:08 am | Permalink

    When are you going to feature Morrissey?

  11. Posted February 20, 2011 at 10:16 am | Permalink

    Hmm. I don’t really like him much, but I’m not sure I could tell you why. The voice just doesn’t speak to me.

    Faves: Ella Fitzgerald, Billie Holliday.

    • Dominic
      Posted February 20, 2011 at 2:02 pm | Permalink

      I would say the young Sinatra was fab but I do not think his voice survived past middle age so listen to the earlier recordings rather than those after say the 1960s. The same for Bing & Asataire, my fave. Also it always depends on the type of song that the singer chooses, so you can like the singer but not the song, or the song but not the singer. Hmmmm… That is a rather inane cooment perhaps, but true I reckon.

  12. Gregory Kusnick
    Posted February 20, 2011 at 10:49 am | Permalink

    As a teen in the late ’60s and early ’70s I detested Sinatra, not just because he was of the pre-rock-n-roll generation, but also because, looking back on it, his music of that period was just not as good as his earlier stuff. He had an aggressively hip, over-syncopated, punchy delivery that in my opinion completely negated the melodic qualities of his voice. Like he was deliberately trying to distance himself from what made him famous in the first place. (Joe Piscopo parodied this style very effectively on SNL.)

    It wasn’t until I heard “Young At Heart” on the soundtrack of The Front in 1976 that I started to realize that hey, this guy really can sing.

  13. Posted February 20, 2011 at 10:53 am | Permalink

    Sirius satellite radio has had channel 75
    “seriously Sinatra” I find much of his stuff too slow. My two favorites of that era were, and are Vic Damone (On the street where you live)and Tony Bennett
    (San Francisco) and many others.

  14. Posted February 20, 2011 at 10:58 am | Permalink

    Is there anyone who doesn’t like him?

    I never liked him. That’s why we consider taste in music to be subjective.

  15. Robo
    Posted February 20, 2011 at 11:08 am | Permalink

    After Satch, Frank was the man who laid out the template for male popular singing in the 20th Century. And there’s more than a trace of Sinatra in Bob Dylan’s approach to phrasing. After those three, it’s all derivation.

  16. Robo
    Posted February 20, 2011 at 11:09 am | Permalink

    Sorry, forgot this great line from Bing Crosby:

    “Sinatra is a singer that comes along only once in a lifetime, but why did it have to be my lifetime?”

  17. Gordon
    Posted February 20, 2011 at 11:30 am | Permalink

    I do not like Sinatra or Crosby or any of the crooners because they always sound off-key, slightly out of tune.

    • Filippo
      Posted February 21, 2011 at 10:04 am | Permalink

      Andy Williams? Johnny Mathis? Nat “King” Cole? Among others.

  18. 386sx
    Posted February 20, 2011 at 11:33 am | Permalink

    Bing, Frank, and Dean all singing together. Ironically singing a song called “Together”. Irony alert!

  19. Vern
    Posted February 20, 2011 at 11:47 am | Permalink

    I never cared for Sinatra myself. But he had some of the best bands backing him up. When I hear him sing I try to ignore the vocals and enjoy the band.

  20. mordacious1
    Posted February 20, 2011 at 12:52 pm | Permalink

    Whether you don’t like him as a person, or even his voice, it still stands that he was one of the great ones. I prefer Tony Bennett myself, or Al Martino (who probably won’t make Jerry’s list).

  21. Andrew EC
    Posted February 20, 2011 at 12:59 pm | Permalink

    After Sinatra’s “New York, New York” was co-opted by the hated Yankees, I couldn’t bring myself to listen to Ol’ Blue Eyes anymore.

  22. ZenLady
    Posted February 20, 2011 at 1:52 pm | Permalink

    I have always loved Sinatra’s music. I used to play his greatest hits album every Saturday morning and (along w/ my kids), clean house it.

    Unfortunately, I ruined his music for my kids, who tell me that anytime they hear his voice, they feel compelled to grab the pledge and a clean rag.

    (However, you shouldn’t really get “pissy” just because other people don’t feel the same way. After all, you DID ask.)

    • Filippo
      Posted February 21, 2011 at 10:16 am | Permalink

      Armed with an iPod, I can do the most onerous, groady grunt house and outdoor work (shoveling dirt, cleaning toilets), so long as I can listen to great music, and, if within range of wireless, keep zee leetle gray cells wonderfully occupied listening to great lectures, discussions, and debates including the likes of Hitchens, Chomsky, Lewis Lapham, Richard Heffner (The Open Mind), Dawkins, Coyne, “The Ascent of Man” (Jacob Bronowski) and on and on.

      Re: “(However, you shouldn’t really get “pissy” just because other people don’t feel the same way. After all, you DID ask.)”

      Is this to say that he should adopt an “accommodationist” stance on the matter? To what extent? Beyond “reasonable and appropriate”?

      As the song goes, “How many seas must the white dove sail?”

  23. Posted February 20, 2011 at 2:01 pm | Permalink

    I love love love the Frank & Dean duet. Although Dean has my heart, I still love me some Frank, too.

    And this is one of my favorite things ever: Frank, Dean, and Judy Garland singing together. I believe it’s from The Judy Garland Show, which aired from ’63-’64, but I’m not absolutely certain.

  24. Dominic
    Posted February 20, 2011 at 2:04 pm | Permalink

    Sid Vicious cover of My Way – brilliant ‘deconstruction’ to use a word I don’t know the meaning of!

  25. TrineBM
    Posted February 20, 2011 at 2:18 pm | Permalink

    I’ve always liked Sinatra – without loving him. His phrasing is impeccable, and the bands he sang with!! WOW.
    But Dean … sigh … his voice is just soooo much better. No he doesn’t quite have the same edge, and the music he sang was often more corny than good. But the voice!!!

    • Diane G.
      Posted February 20, 2011 at 11:22 pm | Permalink

      + 1

  26. Tim
    Posted February 20, 2011 at 2:28 pm | Permalink

    Like many, perhaps most, popular singers Sinatra resonates with me because he reminds me of my mother listening to him. Imagine my surprise when it turns out that my adult daughter is a fan of Michael Buble – who seem’s like Sinatra redux (and, hopefully, a nicer guy.)

    • Diane G.
      Posted February 20, 2011 at 11:23 pm | Permalink

      My college student daughter’s a big Buble fan too!

  27. Rik
    Posted February 20, 2011 at 2:33 pm | Permalink

    Got to love Billie Holiday. Going back a bit but still classic. The 30’s and 40’s had some great artists.

  28. Michelle B
    Posted February 20, 2011 at 3:33 pm | Permalink

    Sinatra does nothing for me. As a kid, I would ask my parents why are they saying he is singing when he is talking?

    I need some fireworks in the voice, and pop singers usually do not supply that aspect, except for non-American singers like Edith Piaff and Jacques Brel. The only American pop singers that I enjoy are Patsy Cline and Roy Orbison (and they were both cross-overs from other genres). Barbara Streisand is too glib/slick rather possessing depth to my ears, talented that she is.

    • Filippo
      Posted February 21, 2011 at 10:31 am | Permalink

      “I need some fireworks in the voice.”

      I can perhaps see that in Roy Orbison, whose voice at least one pop music critic has favorably claimed to possess high-octane operatic qualities.I.e., “fireworks.”

      I don’t see it with Patsy Cline unless by “fireworks” you mean those such as Ulysseus felt when, strapped to the ship’s mast, he begged his deaf sailors to untie him so that he might respond to the Sirens’ calls.

      For viscerally-compelling vocal fireworks and tone and timbre of voice to set ones heart palpitating, I recommend Mario Lanza and Sergio Franchi.

      To what extent is Barbara Streisand “too glib/slick”? (Whatever exactly those subjective terms mean.) 3 21/37%? Pi%? Sqr rt of -1%?

      Suppose she is in her later albums. Not in those first few.

      Can one imagine Patsy Cline singing, “Anywhere I Hang My Hat Is Home”?

  29. Michelle B
    Posted February 20, 2011 at 3:36 pm | Permalink

    Now American Blues singers, wow, just wows. They have my heart in their hands.

  30. Posted February 20, 2011 at 5:11 pm | Permalink

    I can “appreciate” Sinatra, but I don’t really enjoy him. He just sounds a little
    too smug for me. I’d have to agree with
    Michelle B regarding blues vocalists and
    Roy Orbison. Orbison always seemed like
    an opera singer who got the right idea.
    Fats Domnino had a great voice, but I’m
    not sure if you’d call him a pop or R&B
    singer. I just like the happy/sad quality
    of his voice and the way it makes you feel good, like an old flannel shirt.

  31. Josh
    Posted February 21, 2011 at 5:24 pm | Permalink

    I could never really get into Sinatra, or any of the white singers from this time period. Their voices just sound so pompous and smug, as Rik G said.

  32. latsot
    Posted February 21, 2011 at 5:36 pm | Permalink

    I love Sinatra, but I’m going to cast a vote for Nat King Cole. Perhaps he didn’t have Sinatra’s sense of style and ability to work an audience, but his voice was just extraordinary.

  33. Posted February 22, 2011 at 2:14 am | Permalink

    Yes, there’s someone who doesn’t like him: me. I’ve never understood why people think Sinatra is so great. To me his voice is pedestrian and nothing out of the ordinary. Bland. Boring. I used to go to an Italian restaurant that played nothing but Sinatra as background music and I had to stop eating there.

  34. JBlilie
    Posted February 22, 2011 at 1:59 pm | Permalink

    I like Sinatra fine. But he does something almost no one else could get away with (and some people hate it): He doesn’t stick to the beat.

  35. Joe Fogey
    Posted February 22, 2011 at 4:01 pm | Permalink

    Not a very profound analysis, but it’s the bland/smooth cliche-ridden schmaltz of Sinatra and co that made radio in England so boring until rock’n roll and later the beat groups began to blow the mellow old cobwebs away. Then we got super-groups and stadium rock to lull us to sleep – but punk woke us up. I’d rather listen to Peter Tosh than Bob Marley, and I’d rather listen to Johnny Rotten that Frank Sinatra.

    As William Blake said, “Damn braces, bless relaxes”.

  36. Launcher
    Posted February 23, 2011 at 7:29 pm | Permalink

    I’m not sure we’d all define “our era” the same – certainly Sinatra’s prime is a full generation (or two, heading into three) ahead of my favorite artists.

    Anyway, I’ve long considered Sting one of the most distinctive and hard-working artists of my time. He’s incredibly diverse and always entertaining. That his repertoire goes well beyond the “pop” realm only adds to his appeal.

  37. Jeffrey Shallit
    Posted February 27, 2011 at 10:58 am | Permalink

    I can’t stand Sinatra. For me, he absolutely oozes insincerity. I’d much rather listen to Bruce Springsteen.

    If there is a hell, it will have a Sinatra soundtrack.

    But, you know, he was pretty damn good in Von Ryan’s Express.

  38. chris
    Posted March 17, 2013 at 6:47 am | Permalink

    I know I’m late to this thread but in reading the comments below I can see that many people have just not accurately looked at his music and career. To blanket say he sang out of tune or never sang songs he didn’t mean or scooped to all his notes is just ignorant. It comes from more of a personal taste stance rather than basis in fact. Do your homework first. His music and artistry will be remembered and studied long after we’re all here to comment on it!

    remembered long after

  39. nat
    Posted March 25, 2013 at 7:03 am | Permalink

    if you had to choose a singer for all the technical ability of Sinatra, yet more toned and ranged with far more voice control and flexibility and sounding incredibly fantastic then no one can match the unique voice of JOHNNY MATHIS even Frank Sinatra rated him as one of the few singers he admired andit was a jealous Sinatra who mocked Mathis, foolishly at times, shame on Sinatra.

%d bloggers like this: