If pressed, a lot of people nowadays, but certainly not all, could name three or four singers of American popular standards. One name they would probably be able to come up with would be Nat King Cole. Most people would know the name, the fact that Natalie Cole was his daughter and that he sang Christmas music. But there is SO much more going on with Nat Cole that needs to be known and appreciated. As opposed to an in depth look at his life and career, what I propose to present is a quick run-through, focusing on the wonderful music he recorded and how it varied throughout his tenure as one of the smoothest voices in popular song. Lastly, I’d like to run down, in order, the ten greatest recordings of the man born Nathaniel Coles.

There are a few key things about Nat Cole that I would present to a beginner who is wanting to know what all the fuss is about and who is wanting to know what to listen to based on their interests. The first thing I like to point out – the thing that perhaps makes Cole cooler than anything else – is that, at the beginning of his career, he was a jazz pianist. And he was good. He was a student of the recordings of the great Earl “Fatha” Hines and Cole was considered one of the leading jazz pianists of the late 1940’s-early 1950’s. So much so that he was the featured pianist on the original “Jazz at the Philharmonic” concerts originated by Norman Granz that featured all-star line-ups of the finest jazz musicians in the land. Also notable is the make-up of Cole’s early trio – piano, guitar and bass. Those three instruments in particular (no drums) was a unique set up especially in the big band era and it was emulated by many combos that emerged later. It’s amazing to think that, with a voice like his, Nat originally sang only occasionally. Legend has it that he sang live for the first time because a drunken customer demanded it. Nat sang “Sweet Lorraine” and was tipped 15 cents. The recordings of the Nat King Cole Trio – with or without vocals – are wonderful. They present perfect, smooth, small combo jazz. It’s only Nat’s tremendous success later as a vocalist that somewhat relegates this part of his career to the background. In 1942, songwriter Johnny Mercer founded Capitol Records and a year later Johnny signed Nat and the trio to the label and they began enjoying great success there. The trio was so successful that the revenue from their record sales propelled Capitol to the forefront of the record business, allowing them to build the famous Capitol Tower as a home base. The world’s first circular office building is often referred to as “the House That Nat Built”.

By the early-to-mid 1950’s, Nat had – unfortunately, some jazz purists lamented – jettisoned the small group sound and stepped to the fore as one of the premier proponents of the smooth vocal pop tune with orchestral accompaniment. In 1953, Nat scored a hit of immortal proportions with his first recording with an orchestra: “The Christmas Song”. Many hit singles followed and Nat was paired with all the major arrangers of the day: Nelson Riddle, Gordon Jenkins, Billy May. He delivered album after album of sublime vocals. Indeed, you could look at Nat Cole as an “album artist”. Yes, he placed many tunes on the charts (28 top 40 hits between 1954 and 1964) but his main contribution to traditional pop or jazz vocal is a string of excellent albums with great arrangers and attractive album covers.

Nat Cole was a pioneering black entertainer. He became one of the first African American’s to host his own show – The Nat King Cole Show aired for a year starting in 1956. The show was well done and featured many big stars of the day but it could not maintain sponsorship as many brands were hesitant to support so visibly a black artist, even one as universally loved as Nat Cole. Finally, Nat had to shut the show down. Referring to the inability to maintain sponsorship, Nat quipped notably “Madison Avenue is afraid of the dark”. Nat was a quiet and gentle crusader for equal rights. He was an inspiration to all black entertainers at the time. Nat had married singer Maria Ellington and eventually had five children, two of them adopted. During his peak years, Nat moved his family to an affluent neighbourhood in Los Angeles where they were met with hostility from their neighbours. Nat attended a community meeting at which a spokesmen boldly stood up and proclaimed that the area did not want any “undesirables”. Nat responded by rising and saying “Neither do I. If I see any undesirables, I’ll let you know”. Nat’s home was vandalized (racial slurs burned into the lawn) and a family pet was killed (poison meat thrown over the fence). Nat soldiered on, dignity intact.

Into the 1960s, Nat began to work with lesser known arrangers and orchestrators. The results yielded many additional hits – “Ramblin’ Rose”, “Dear Lonely Hearts”, “Those Lazy-Hazy-Crazy Days of Summer” – but the old-timey, sing-along quality of this period represented the nadir of Nat’s recordings. Even still, with his vocal charm, he was able to squeeze out a couple more charming tracks. He does a version of “The Girl from Ipanema” on the last album released during his lifetime that is excellent and “Let Me Tell You Babe” is a track released after his death that purists probably hate as it has a late-60’s-pop-soft-rock sound to it but I like it. Throughout his career, Nat had been one of the sharpest dressed cats in the business, always in a sharp suit or sweater, sometimes sporting a fedora – and always, but always, smoking a cigarette in a cigarette holder. This wretched vice became the undoing of Nat King Cole. You have to understand that – and if you look into it, you’ll see it’s true – everybody loved Nat Cole. All reports indicate that there was not a classier person in show business. A loving husband and father, he quietly blazed a trail for black artists and was a genuine human being. When Nat fell ill in the early 1960’s, many friends and associates expressed their concern to him. The hazards of nicotine were not as widely known as they are today and people were simply worried that his constant smoking would wreck his voice and his health. A visit to the doctor confirmed a lung cancer diagnosis. The historic Surgeon General’s report confirming the negative effects of cigarette smoke was issued in January of 1964. Nat Cole received his death sentence 9 months later. The disease progressed rapidly and Nat was confined to hospital. He left one last time for an afternoon drive in February of ’65 looking gaunt and aged. He graciously allowed photographers to take pictures of him and his wife outside the hospital. As Mr. and Mrs. Cole drove away, the photographers wept.

Nat King Cole died on Valentines Day, 1965. In his last days, he reportedly pressed his doctors to get him well so that he could tell people to quit smoking. His cancer death – along with the Surgeon’s General report – were early events in the worldwide crusade against the evils of smoking and its link to cancer. While he was not without his transgressions, Nat Cole was truly and dearly loved by his family, his friends, all of his contemporaries, the press, the recording industry and fans the world over. His legacy is unique and his gifts to all of us are immense.

Let’s return to that which never dies; the music. You have to be careful with record companies. They will often stick with an established and well-known group of songs and – with little deviation – reissue these tracks ad nauseam. Beware the many redundant ‘greatest hits’ packages. It seems, with Cole, that many of his most popular “hits” are actually some of his most mediocre recordings. Keep in mind that, as you scan this list, you may not see songs you thought you would. In compiling this list, I took many things into consideration and I found that sometimes ‘immense worldwide familiarity’ did not necessarily indicate a quality recording. Not only are there many Cole songs you know by heart and you don’t need me to tell you about them but also, as I’ve said, the recordings embraced by the masses don’t always represent high quality material. Helping you to know what is good based on what you like (trio jazz or pop vocal) is the goal of this list of the ten greatest recordings of Nat King Cole.

10. “Baby, Baby All the Time” (1946)  This track from the Nat King Cole Trio was written by Bobby Troup. I notice that the little known Troup penned two songs in this top ten. Better known as the husband of chanteuse Julie London and as Dr. Joe Early on Emergency!, Troup wrote jazzy little numbers for small jazz combo settings and Cole and company introduced this track which quickly became a jazz standard. It’s gentle gait and pleading lyrics are straight down the Trio’s alley. It’s a cozy piece that serves as a delightful example of what Cole and his trio did best.

9.  “That’s All” (1953)  Written in 1952 by singer Dick Haymes’ younger brother, Bob, here’s another standard that was introduced by Nat. This song is unique in that it really had no initial “hit” phase and instead went straight to “standard”. Bobby Darin helped popularize it when he presented it as the energetic title track of a 1959 album. Nat’s version was one of his early successes with the great conductor and arranger Nelson Riddle. Riddle’s name is synonymous with the very best recordings of Frank Sinatra but the Chairman himself has said that it was Nat’s records with Nelson like “That’s All” that made him want to work with the arranger. This recording of Cole’s is sublime and is an early example of him plying the sound that would become his trademark.

8. “Answer Me, My Love” (1954)   This song has its origins as a German piece to which English lyrics were added. It was a hit in 1953 for both David Whitfield and Frankie Laine. Another of Cole’s outings with Nelson Riddle, Nat had the best-selling version of the song which was popular throughout 1954. It is another marriage of the very finest of Cole’s ballad singing and absolutely gorgeous strings and orchestra directed by Riddle. The chorus of white, female voices detracts from it only slightly. Like “That’s All” before it, this track is quintessential, sigh-worthy Nat Cole balladry. Celestial.

7. “Sweet Lorraine” (rec. December 15, 1943)  Perhaps the oldest song on this list, “Sweet Lorraine” was written in the late 1920’s and featured lyrics by Mitchell Parish who also contributed the words to such perennials as “Stardust”, “Moonlight Serenade” and “Sleigh Ride”. It is another song that has become a jazz standard. This is a significant recording in Nat Cole’s oeuvre. Earlier recordings than the 1943 edition I’ve chosen here represent the first of Nat Cole’s truly fine vocals. Singing this song early on in clubs gave audiences their first taste of Cole’s fine voice and provided him with an opportunity and the confidence to hone his vocal skills. This Trio recording from ’43 – like “Baby, Baby…” – is just another fine example of this small group at it’ subtly swinging best. You can notice a slight lisp that never gave Nat much of a problem – except when he sang “Sweet Lorraine”. Listen for him to sing “I’m as happy as a baby boy playing with a brand new choo-choo choy“ – as opposed to “toy”. Three years after this recording, Frank Sinatra recorded a version also employing the Nat King Cole Trio’s intimate sound. After Cole’s death, Tony Bennett sang “Sweet Lorraine” in tribute on his If I Ruled the World: Songs for the Jet Set album (1965).

6. “L-O-V-E” (1964)  Our first selection on this list from the latter part of Cole’s career. Actually, the last part. “L-O-V-E” is the title track of the final album of Nat’s to be released during his lifetime. He finished making the album with his final recording sessions in December of ’64. This means that this swinging number was recorded so sublimely by Nat when he was already sick with the disease that would take his life only months later. This track was written by legendary German Bandleader Bert Kaempfert and Nat, again, was the first to sing it. Although any list of the finest recordings of Nat King Cole will undoubtedly be laden with ballads, the cat could swing, as this song attests. It starts off gently trotting and sounding like Bobby Darin’s “Hello, Dolly!” and then – also like the Darin track – builds to a brash climax. It is a joy to sing along to and is a prime example of how good Cole was at uptempo material.

5. “(Get Your Kicks on) Route 66” (1946)  I realized as I was compiling this list that Nat Cole can give Fred Astaire a run for his money when it comes to introducing some of the most enduring songs in the history of American popular music. Here he is again with his Trio being the first to record another standard written by Bobby Troup. In this case, the song is considered to be an R&B standard and has been covered by an extensive and varied list of artists: Bing Crosby, Chuck Berry, the Rolling Stones, Them, Depeche Mode, the Cramps and John Mayer. Cole’s first version with his trio is an uptempo swinger featuring lyrics about traveling the expanse of the American country side on the famed highway. It is one of the very few quintessential Cole recordings not only in terms of quality but also popularity. An absolute delight featuring Cole in great voice and displaying his light-fingered chops on the keys.

4. “Straighten Up and Fly Right” (1943)  A companion piece to “Route 66”.  Many similarities exist between these two seminal Trio recordings. The main difference being that while this is also a song that Cole introduced to the world before it became a standard, this was one that he actually wrote himself. He took the lyrics from an old, black folk tale that Cole’s father – a Baptist minister – had used as a basis for a sermon. A lighthearted vocal from Nat is paired with the Trio’s charming brand of breezy small combo jazz. The song’s popularity has been sustained through uses in the 2010 video game Mafia II and more recently in the TV series This Is Us.

3. “That Sunday, That Summer” (1963)  And here we are at probably the only recording on this list that I would really have to defend. This song was published in 1963 and, as far as I can tell, Nat Cole was, again, the first to record it. The problem is it appeared on his Those Lazy-Hazy-Crazy Days of Summer album, the title track of which went to #6 for Nat in the spring of ’63. He followed that up with an album of the same name made of turn-of-the-last-century sounding songs singing the praises of summer. A lot of banjo. The album was successful for Nat but it is a good example of one of those times when public adoration did NOT mean quality work. The title track is delightful but this old-timey setting simply does not mesh well with Nat’s dulcet tones. The exception is “That Sunday, That Summer”. This is the only track on this list that charted in the top 40 on the pop charts during the “modern era” of the tracking of chart activity which began in 1954-55. Fittingly, in September of ’63, after summer frolicking had given way to autumn studies, the nostalgic “That Sunday” spent 9 weeks on the charts peaking at #12. The banjo is present but subdued and adds to the wistful nature of the lyric and compliments Nat’s dreamy vocal. Again, we’re assaulted with an inappropriate chorus of angelic female voices but it doesn’t matter here. The track never appears on any compilations you’ll find at the record store but that just supports my theory that the real ‘best of Nat’ is not that easily found. Seek out this gorgeous number and drift away.

2. “The Christmas Song (Chestnuts Roasting on an Open Fire)” (1961)  Here’s a song that deserves its own post. Let’s just take it slow and from the beginning. This song was written by singer Mel Tormé and Bob Wells. It was written on an exceedingly hot day in an effort to keep cool. Here’s also another example of a new song making its way to Nat Cole first. The Nat King Cole Trio recorded the song first in 1946. Cole then convinced Capitol to let him record it again months later but this time with a small string section – an auger of things to come for Nat. This second version became a massive hit on pop and R&B charts. Cole again recorded an orchestral version during his productive year of 1953 with Nelson Riddle. Nat’s fourth recording of it took place at Capitol Studios in March of 1961 with the Ralph Carmichael Orchestra. This is the version that you hear every Christmas. Cole issued a Christmas LP in 1960 called The Magic of Christmas and then, in 1963 while his newest version of “The Christmas Song” was becoming legendary, Capitol decided to reissue The Magic of Christmas as “The Christmas Song”, adding the new title track and deleting “God Rest Ye Merry, Gentlemen”. This version of his Christmas album (complete with new cover replacing white kids admiring tree with Nat chilling in sweater by the fire) has sold untold scores of copies and is still a seasonal favourite. (All this, of course, makes Nat’s “God Rest Ye Merry” the lost carol!) “The Christmas Song” – the track – is sublime but here’s the funny thing: Nat Cole has an incredibly huge rep as a Christmas artist but the truth is that the rest of “The Christmas Song” album is quite boring and plain and since Nat never again recorded a full album of Christmas music this means that his huge Christmas rep is based solely on these three minutes of absolute perfection. There may be no finer recording in Nat’s catalog than his 1961 version of “The Christmas Song”. From the opening two notes, this tune manages to encapsulate all the warmth, peace and joy, all the emotion of the Christmas season. Nat’s vocal is the pinnacle of excellence and the unheralded Ralph Carmichael provides an appropriately lush setting featuring a wonderfully mellow guitar solo. It conjures up all the wonderful feelings usually associated with a night in late December relaxing in a warm room lit only by your Christmas tree and surrounded by those you love. The only reason it’s not number one on this list is because it would’ve been too easy. It benefits so much from these external things.

#1 “Stardust” (1957)  “The Christmas Song” is a resplendent recording. However, part of its immense charm certainly comes from the Christmas season itself and all of our thoughts, feelings and memories regarding it. “Stardust” does to you what that Christmas classic does to you but all on its own. “Stardust” is the aural manifestation of Nat King Cole in all his glory. This standard among standards was written in 1927 by the great Hoagy Carmichael (who not only wrote great songs but possessed one of the greatest names in history) with lyrics added by Mitchell Parish. It is one of the most recorded songs of the 20th century with 1,500 recordings of it to date. Nat recorded his version in December of 1956 for his album Love is the Thing. The orchestral accompaniment for this album was arranged for strings alone and conducted by the great Gordon Jenkins. Jenkins provides strings so lush that “Stardust” takes on an ethereal quality. It seems to drift down out of the heavens. Nat does well with any type of material but his legacy and his strength is definitely ballad singing and “Stardust” is the quintessence of this strength and represents one of the peak experiences of vocal balladry in the history of recorded sound. It is that good. Love is the Thing was the first of four albums Nat would make with Gordon Jenkins. This album was one of the earliest stereo albums made at a time when such albums were made specifically for a niche stereo hi-fi market. The album was also very successful for Nat reaching #1 on the charts while “Stardust”, released as a single, reached #79. What more can be said? It is a flawless vocal performance wrapped in a plush and almost surreal environment of dreamlike beauty. The album is perhaps the finest single moment in either Nat’s or Gordon’s career and provides us with the finest example of the art of Nat King Cole.

In compiling this list one of the many things I discovered is that looking at single recordings maybe isn’t the best way to explore Nat Cole. As Bennett has said, it’s about the catalog, the whole, as opposed to single moments. Nat’s entire career is a joy. Do yourself a favour and grab an album – not a compilation – of his. You won’t be disappointed.

Honourable Mentions: “Unforgettable”, “Walking My Baby Back Home”, “Mona Lisa”, “Embraceable You”, “When I Fall in Love”, “Too Young”, “Somewhere Along the Way”, “Say It Isn’t So”, “Lights Out”