We finish up our look at the recordings of Frank Sinatra with Part 4. I’ve tried to break down Frank’s career into sections that represent different eras. We started in the Big Band era and Frank’s work with Harry James and Tommy Dorsey then followed Frank as he went solo and recorded for Columbia Records. In Part 3, Frank moved to Capitol and enjoyed a reign that is like no other in history. Now, in Part Four, we look at a point in Frank’s career that could be called the ‘victory lap’. By the late ’60’s, with nothing left to prove, Frank just made records. Or he didn’t. And they charted. Or they didn’t. None of these things mattered anymore. He was Sinatra. In the late 1960’s, musical tastes and trends went through a mammoth transition. Things had been changing since 1956 but singers of popular song like Frank and Dean Martin and others had continued to stay somewhat relevant and also to enjoy some pop chart success. But by the time Frank turned 50 near the end of 1965, he himself was ready to change and capitulate somewhat to the changing tides in popular music.

Part Four encompasses Frank’s recordings between the Strangers in the Night album, released in May of 1966, and the end of his recording career which, in this case, we are calling L.A. is My Lady from 1984. I’ve chosen the Strangers album as a turning point in his recording career because of the marked difference between the Moonlight Sinatra album, released March of ’66 and Strangers two months later. While there may have been indicators previous to Strangers, that album introduced Frank in a ‘contemporary’ setting – the back cover declared “Sinatra Sings for Moderns”. Frank began to embrace the sounds of the time, if, at first, only slightly. Strangers features Frank’s take on two recent Tony Hatch-written hits for Petula Clark. “Call Me” was soon to become an easy listening standard and “Downtown” had been a major international hit for Clark in 1964. FS sounds comfortable breezing through “Call Me” but he seems to have disdain for “Downtown” which comes off weakly. Frank even manages to make an “ewww” sound during the recording. The other two contemporary-sounding numbers on this album would fare much better historically. The title track became Frank’s biggest chart hit, reaching the #1 slot on the pop charts, the easy listening charts and the UK singles chart. The song won Frank two Grammys and added a third for Best Arrangement for Ernie Freeman. “Summer Wind” appears second on the album after the title track. It topped the easy listening charts but only reached #25 on the pop charts. Through time, however, the song has become legendary as distinctly “Sinatra” and one of his most revered and referred to songs. These four tracks on the Strangers album were presented by arranger Nelson Riddle in a contemporary setting, emphasizing the rhythm section and a jazz organ Riddle utilized throughout the record. On the strength of the title track, Strangers in the Night has become Sinatra’s most successful and biggest-selling record and it ushered in a new pop/rock sound for the Chairman.

Frank Sinatra’s records from the late 1960’s and into the 1970’s sound like sunset to me (Later That Day…). They just have a unique feel. They always bring to mind the era in which they were released and how, at that time, Frank was perhaps looked on as old fashioned. But he still had his legion of fans who hung on every word. I always feel like these fans literally traveled through their lives with Frank. In the late ’60’s, he was in his 50’s just like they were. The fans may have felt older and out of touch, like Frank was perceived. Maybe their kids had left the nest and they found themselves in a new era of their lives. Maybe they looked at their spouses differently. Maybe they felt a strain. But – like Bruce Springsteen a generation later – Frank was right there with them. To his fans, he was still the pinnacle. To me, there is all this story to these recordings. There is an oaken quality to them. They sounded like the times – which was a new thing for Frank, having presented the standards for all his life – and yet they sounded different than the other records being released at the time. There was a quality, a class about them. It’s hard for me to describe this feeling in words – you’re either going to feel it or you’re not. I say all this to explain that the Top Ten list that follows does not represent the ten best recordings of Frank’s from this era. They are the ten recordings that exemplify this feeling best. Subsequently, nothing from She Shot Me Down (1981) appears on the list although this is his last truly great album and features many stellar performances. There is nothing from his 1984 outing with Quincy Jones, L.A. is My Lady, mostly because it was generally a return to standards and contains a high ’80’s polish which goes against the vibe I get from these years. Of the two Duets albums I won’t even speak.

After Strangers in the Night, Frank continued to record good albums consisting of some of the best from the current crop of pop songwriters while still fitting in some traditional pop sounds. If you were to pick up any of these albums, you would hear exactly what I’ve been trying to get across to you. All of them are good but I can particularly suggest Cycles and Watertown. And I simply must say a word about Frank’s 1967 release Francis Albert Sinatra and Antonio Carlos Jobim. Although the bossa nova craze of the early ’60’s had died down, Frank got together with the architect of that sound, Jobim, and recorded simply one of the greatest albums of his career. It is one of my all-time favourites and it features some of Frank’s best singing. It is a cruelly short album but is absolutely gorgeous. Again, the reason the songs don’t figure on my list is that they don’t fit the ‘vibe’ although they are some of the finest vocals of his career. Sinatra ‘retired’ for a year-and-a-half in 1971 and returned in ’73 with Ol’ Blue Eyes is Back. Over the next 11 years, he would record only four more albums. Without further ado, here are the ten recordings that best reveal the wonderful sound of Frank Sinatra between 1966 and 1984.

10. “That’s Life” (1966 – from That’s Life) — A great example of that hybrid sound of Frank’s from this time: hip and current but still old school classy. This dynamic recording was released as a single and reached #5 on the pop charts in this era of the new rock sounds. Helping to make it sound hip was undoubtedly the personnel that played on it, consisting of some of the Wrecking Crew, the best studio musicians of the day: Glen Campbell, Hal Blaine, Plas Johnson and Darlene Love. Legend has it that producer Jimmy Bowen was looking for a certain sound from Sinatra for this song. He just wasn’t getting it but how do you tell Frank Sinatra that he’s not really doing it the way you want it? So, Jimmy decided to keep calling for additional takes which was sure to rile the Chairman. Sure enough, eventually Frank was ticked enough to growl through the record the way Bowen wanted. You can certainly hear it, especially near the end.

9. “Somewhere in Your Heart” (1964 – single, 1968 – from Frank Sinatra’s Greatest Hits) — Here’s a song that no one would ever call one of Frank’s best. It appears on this list partly in honour of Frank Sinatra’s Greatest Hits. The first album in Sinatra’s catalog to claim to be a ‘best of’, this album does not contain anywhere near his greatest hits. What it does contain is singles from the era that serve as perfect examples of the “feel” I was talking about. Non-descript, easy listening, adult pop. Mature, contemporary and almost bland, “Forget Domani”, “Tell Her (You Love Her Each Day)” and “When Somebody Loves You” are delightfully interesting to listen to in the proper context. “Somewhere in Your Heart” is the best of the bunch and, although it was released as a single in 1964, it contains that late ’60’s feel I love.

8. “I Will Drink the Wine” (1971 – from Sinatra and Company) — An odd album from Sinatra. It was supposed to be a follow-up to his legendary bossa nova album with Antonio Carlos Jobim but at the last minute it was changed. In the end we got a record with a first side of great new songs with Jobim and a second side of middle-of-the-road pop/rock. Sinatra covers “Leaving on a Jet Plane”,  “(Just Like Me They Long to Be) Close to You” and “Bein’ Green”. Two other songs on this side are “Sunrise in the Morning” and “I Will Drink the Wine”, which has some interesting lyrics. It’s as if Sinatra is passing on the whole hippie scene and longing for something more substantial: “Someone gave me some small flowers, I held them in my hand. I looked at them for many hours, I just didn’t understand…I’ll give you back your flowers and I will take the land. I will drink the wine”. This song went to #16 in the UK.

7. “There Used to Be a Ballpark” (1973 – from Ol’ Blue Eyes is Back) — Sinatra returned from a brief retirement with a new nickname. This album has a great title (Frank’s name doesn’t appear on the jacket) and a great photo on the cover. Interesting songs on this album. Some of them sound like showtunes; big songs with big sounds. Wordy with heavy orchestration. Ostentatious. Like other things in the 1970’s – neck ties, lapels, Robert Plant’s hair, Freddie Mercury’s voice – the songs here are audacious and brimming with bombast. Four of the nine songs were written by Joe Raposo, who wrote the aforementioned “Bein’ Green” for Kermit the Frog. “There Used to Be a Ballpark” is Raposo’s sad lament of a bygone era, the lyrics also perhaps serving as a commentary on Sinatra’s career at this point and the theme of this list. “And the sky has gotten cloudy when it used to be so clear. And the summer went so quickly this year…” It’s wonderfully orchestrated by Gordon Jenkins and the lyric reminds me – unfortunately – of “This Used to Be My Playground”.

6. “What’s Now is Now” (1970 – from Watertown) — Here is a bright, shining moment from a harrowing album. Sinatra gave birth to the “concept album” in the mid-’50’s and he returns to it here. Watertown is the heart-breaking story of a man losing his wife and the mother of his two children to the lure of the big city. The songs were co-written and produced by Bob Gaudio of the Four Seasons. It is Frank’s only album to not crack the Top 100 and it’s the only time in his career that he did not record live with an orchestra – he added his vocals to pre-recorded tracks. The album is absolutely crushing to listen to. The ending, devastating. “What’s Now is Now” is a wonderful song that lives outside the album due to its inclusion on Frank Sinatra’s Greatest Hits Vol. 2 (1972).

5. “Let Me Try Again (Laisse-moi le temps)” (1973 – from Ol’ Blue Eyes is Back) — Ottawa’s Paul Anka had a knack for adding English lyrics to French melodies. Four years before this, he had added hopelessly pompous words to a French song called “Comme d’habitude” and handed it to Frank as “My Way”. That song may be the one most people identify with Frank but Frank didn’t like it much and neither do true Sinatraphiles. “Let Me Try Again” has a wonderful melody and it fits well on its album owing to it’s grand presentation. Arranged by Don Costa, it is well orchestrated and powerfully sung.

4. “Anytime (I’ll Be There)” (1975 – single) — And here’s Paul Anka again. Paul wrote this one all by himself and Frank put it out as a single in 1975. Full-on, mid-’70’s pop/rock. Female back-up singers pushed forward, strings in the back. Most Sinatra-types likely have no use for this obscure song. For me, it exemplifies the whole aura of Sinatra at this time. When I hear it, I can see the 1975 of my childhood. I see the sun coming up, the market opening for the day, the Italian barbers turning on their lights, stepping out onto the sidewalk. I can’t help but wonder who bought this single when it came out and why? What were they thinking when they bought it and when they played it? Who likes the song now and why? It’s a nugget buried so deep. My mother and stepfather used to run a bar. There was an old jukebox there and this record was in it. When I would hear it, it always amazed me that it was Frank Sinatra. A fascinating and pleasant record.

3. “Love’s Been Good to Me” (1969 – from A Man Alone) — In 1969, Sinatra put out this album featuring the songs of poet Rod McKuen. McKuen was at his peak popularity in 1969 and many of his songs had been recorded by numerous artists. His world-weary, emotional lyrics often lamenting lost love were a perfect fit for Sinatra at this time. “Love’s Been Good to Me” is a song that looks back on a life lived in a more realistic and melancholy way than the bombastic narcissism of “My Way”. Recounting loves past in a voice resigned to living without someone, a voice that accepts past joys with the full knowledge that they may never come again. The knowledge that nothing really lasting and good came out of them but they were satisfying at the time. The singer can still look back with gratitude even though he has nothing now to show for it. Nothing but memories. Another lovely melody and a sensitive and moving orchestration by Don Costa. Johnny Cash had the good sense, late in his life, to record this tender ballad.

2. “Cycles” (1968 – from Cycles) — This album has been savaged by critics as ‘wimp rock’ but this song speaks to me in the same way that “Love’s Been Good to Me” does. Indeed, “Cycles” serves as sort of a companion piece to the McKuen song. Both speak about the vagaries of life and love. I’m not deaf; I know “Cycles” is a little cornball and the lyrics come off as sounding pathetic but I think that here again Frank sounds weary, as if he is comforting the listener by telling us he has been there, too. Maybe it is a bit wimpy to say “So I’m down and so I’m out…” but the fact is that sentiment is real and the travails he mentions in this song are ones dealt with by all of us. A tinkling piano starts us off in waltz time and the orchestra builds as the song goes on. It’s just life but it hurts. And then it doesn’t. Cycles. Very emotive singing; listen to his voice on “I got fired”.

1. “Summer Wind” (1966 – from Strangers in the Night) — This is where I came in. This is the first Frank Sinatra song I ever heard. Before I was into Frank I was into Mickey Rourke and he made a film called The Pope of Greenwich Village that dealt with small time Irish/Italian Mafia. “Summer Wind” was used three times in the film and I watched the film several times, usually in autumn. I tried earlier to explain my whole “oaken quality” thing regarding Frank songs from this era and here is where that feeling originated. The Pope was made in 1984 so the small time criminals had an ’80’s look to them. I was more used to Mafia movies like The Godfather that take place in the ’50’s and ’60’s. So, here I’m seeing the depiction of a ‘crew’ long after the glory days of the Mob have passed. But they’re still doing their thing. Still doing gangster stuff and still listening to Sinatra. Even though by the 1980’s the ship had sailed on so many cool things of mid-century, Sinatra still meant something. There was something about that ’80’s visual paired with this gem from 1966 that really stayed with me whenever it came to latter-day Sinatra. It helped that the film was set in autumn and I watched it in autumn. That seems to go hand-in-hand with my feelings on Sinatra and the ‘autumn’ of his career. The song itself is an absolute classic. It was up second on the Strangers album after that celebrated title track. But it was “Summer Wind”, as the years went on, that emerged as the true favourite, the one everybody loved. Again, here’s older, wearier Frank singing about loves coming and going. The wind blows in gently – is there a more pleasing opening 15 seconds in any other Sinatra song? – reaches a peak and then drifts off; a “fickle friend”, indeed. This was Nelson Riddle’s last album with Frank and his use of organ and saxophone on this track are part of what makes it their greatest collaboration of the ’60’s. Going by feeling alone, this is Frank Sinatra’s greatest single recording. It’s the first one I ever heard and my absolute favourite. (Historical note: cool enough to be used in Blade Runner 2049)

This has been really fun for me. I really appreciate all of you who have read these posts.